Chicago is the great American city. Not the most famous, not the oldest, not the wealthiest, but in the particular combination of architectural grandeur, cultural depth, culinary excellence, lakefront beauty, neighborhood diversity, and sheer urban vitality, it makes a compelling case for being the most completely and authentically American metropolis on the continent. Situated on the southwestern shore of Lake Michigan in northeastern Illinois, Chicago is the third largest city in the United States with a population of approximately 2.7 million, anchoring a metropolitan area of nearly ten million people that stretches across the flatlands of the upper Midwest with the confidence of a city that has always known its own importance.
Chicago’s story is one of almost incomprehensible ambition and resilience. Founded as a trading post at the mouth of the Chicago River in the early nineteenth century, it grew with staggering speed into a commercial and industrial powerhouse, the great hub connecting the agricultural interior of the continent to the markets of the East and the world beyond. It burned almost entirely to the ground in the Great Fire of 1871 and rebuilt itself within a generation into a city more magnificent than the one the flames had consumed, pioneering in the process an entirely new approach to architecture that would define the skylines of cities around the world for the next century and beyond. It absorbed wave after wave of immigrants from Europe, the American South, Latin America, and Asia, each community leaving indelible marks on the city’s neighborhoods, its food, its music, its politics, and its cultural life. It gave the world the skyscraper, the blues, gospel music, deep dish pizza, the improv comedy tradition, the greatest architectural school in American history, and a model of urban public space centered on the magnificent lakefront that remains the envy of cities everywhere.
For visitors, Chicago is one of the most rewarding destinations in the United States, a city that combines world-class museums, an extraordinary architectural heritage, a dining scene of genuine national distinction, a music and arts culture of remarkable depth, beautiful parks and lakefront access, and a quality of urban street life and neighborhood character that feels lived-in and authentic in ways that more tourist-saturated cities sometimes do not. It is also a city of genuine complexity and difficulty, grappling honestly with histories of racial segregation, political corruption, and economic inequality that are inseparable from understanding what it is and how it came to be. Engaging with that complexity honestly makes the experience of Chicago richer, not poorer.
The weather, famously, is an obstacle. Chicago winters are genuine northern winters, cold, windy, and often snowy, and the city’s nickname of the Windy City, while actually derived from the boastful hot air of nineteenth century politicians rather than meteorological conditions, has nevertheless attached itself to a city where the wind off Lake Michigan can cut through the most determined tourist in February. But Chicago’s summers are glorious, its springs and falls are beautiful, and the city’s culture of endurance and good humor in the face of meteorological adversity is part of what makes its people so characteristically warm, direct, and lacking in pretension. Come in summer if you can. Come in winter if you must. Come either way, because Chicago is always worth it.
Getting There
Chicago is served by two major airports, each with its own character and geographic relationship to the city.
O’Hare International Airport is one of the busiest airports in the world and the primary international gateway to Chicago, located approximately seventeen miles northwest of downtown in a suburban setting that makes it feel considerably more distant than it actually is. O’Hare is a hub for both United Airlines and American Airlines and offers direct flights to cities throughout North America, Europe, Asia, Latin America, and beyond. The international terminal handles an enormous volume of transatlantic and transpacific traffic, and the airport’s connectivity makes it one of the most important aviation hubs in the United States. The CTA Blue Line train connects O’Hare directly to downtown Chicago, with trains running twenty-four hours a day and reaching the city center in approximately forty-five minutes. This is almost always the fastest and most economical way to reach downtown from O’Hare, as road traffic on the Kennedy Expressway connecting the airport to the city can be severely congested, particularly during rush hours.
Midway International Airport is smaller, older, and located about ten miles southwest of downtown on the city’s South Side, in a neighborhood context that gives it a more urban and less suburban character than O’Hare. Midway is a hub for Southwest Airlines and also serves Spirit, Delta, and several other carriers, with strong domestic connectivity and a more limited but growing international route network. The CTA Orange Line connects Midway to the Loop in approximately thirty minutes, and the airport’s proximity to the city makes ground transportation generally faster and easier than from O’Hare.
Chicago’s Union Station is one of the great railroad stations of America, a magnificent Beaux-Arts terminal completed in 1925 and still serving as a major hub for Amtrak’s national network. The Capitol Limited connects Chicago to Washington DC and Baltimore. The Lake Shore Limited runs to New York and Boston. The Empire Builder heads northwest to Seattle and Portland. The California Zephyr departs for San Francisco via Denver and Salt Lake City. The Southwest Chief travels to Los Angeles via Kansas City, Albuquerque, and Flagstaff. Several regional routes connect Chicago to cities throughout the Midwest. For visitors from cities within the Midwest, Amtrak service to Chicago is often competitive with flying once airport hassle is factored in. The City of New Orleans route connecting Chicago to Memphis and New Orleans is one of the most historically resonant train journeys in America.
Driving to Chicago from Midwest cities is common and practical, with excellent interstate highway connections in all directions. The parking situation in downtown Chicago is expensive and congested, and visitors arriving by car are generally better served by parking at a hotel or a longer-term garage and using public transit or walking for their time in the city.
Getting Around
Chicago’s public transit system, operated by the Chicago Transit Authority and universally known as the CTA, is one of the best in the United States and the primary mode of transportation for most visitors exploring the city.
The elevated rail system, known as the L, is the most distinctive and visually iconic element of Chicago’s transit infrastructure. Eight color-coded rail lines radiate from the downtown Loop, the central elevated track structure that circles the heart of downtown Chicago and gives the central business district its name. Riding the L, particularly on the elevated sections that pass above city streets and between the upper floors of downtown buildings, is one of the quintessential Chicago experiences and a remarkable way to understand the city’s geography. The lines connect the downtown core to neighborhoods throughout the North Side, West Side, South Side, and northwest suburbs, and the system operates twenty-four hours a day on most lines.
The Red Line is the most useful for many visitors, running north-south through the heart of the city from Howard Street on the far North Side through downtown and south to 95th Street. It connects neighborhoods including Rogers Park, Andersonville, Wrigleyville, Boystown, Lincoln Park, and the Near North Side to the Loop and the South Side. The Blue Line connects O’Hare and Midway through downtown. The Brown Line serves the Lincoln Square, Ravenswood, and Wicker Park areas. The Green Line serves the West Side and the South Side including the historic Bronzeville neighborhood.
The CTA bus network is extensive and serves the many neighborhoods not reached by the rail lines. The Ventra card, available at L stations, provides tap-to-pay access across the entire CTA system. Unlimited ride passes are available for one, three, and seven day periods and are excellent value for visitors planning to use the system extensively.
Rideshare services are widely available and convenient for trips between neighborhoods not well-connected by the L, for late-night travel, and for reaching destinations with awkward transit connections. Taxis operate throughout the city. The Divvy bike share system has become a significant part of the city’s transportation infrastructure, with hundreds of docking stations throughout the city and an expanding network of protected bike lanes. The lakefront trail, running along the shore of Lake Michigan, is one of the finest urban cycling and running paths in the United States.
Walking is excellent in many Chicago neighborhoods, particularly in the Loop, the Near North Side, Lincoln Park, Wicker Park, Bucktown, and the neighborhoods along the lakefront. The city’s grid street system, with numbered addresses increasing predictably from the center, makes navigation straightforward once the basic logic is understood.
Neighborhoods Worth Exploring
The Loop and Grant Park
The Loop is Chicago’s central business district and its architectural heart, a dense concentration of skyscrapers, cultural institutions, theaters, and public spaces that contains some of the most important buildings in the history of American architecture. The elevated L tracks that circle the district give it its name and its distinctive soundtrack. Walking the streets of the Loop is an architectural education in itself, with landmark buildings from virtually every era of the city’s development visible from every block.
The Chicago Riverwalk, running along the south bank of the Chicago River through the Loop, has been transformed in recent years into one of the finest urban waterfront promenades in the country, lined with restaurants, bars, kayak rentals, and public art installations. The river itself, famously dyed green each St. Patrick’s Day, is the site of excellent architecture boat tours that provide the best perspective on the city’s skyline and building history. Chicago Architecture Center river tours are widely considered the finest introduction to Chicago’s architectural heritage available to visitors.
Grant Park is the vast green space east of the Loop between Michigan Avenue and the lakefront, often called Chicago’s front yard and containing some of the city’s most beloved public spaces and institutions. Millennium Park, at the northern end of Grant Park, opened in 2004 and immediately became one of the most successful urban public spaces created anywhere in the world in recent memory. Cloud Gate, the massive reflective stainless steel bean-shaped sculpture by Anish Kapoor known universally as The Bean, has become one of the most photographed public artworks in the United States and a beloved symbol of the city.
The Crown Fountain, two fifty-foot glass towers displaying faces of Chicago residents and periodically shooting jets of water, is another beloved public art installation. The Jay Pritzker Pavilion, a spectacular outdoor performance venue designed by Frank Gehry with a stainless steel bandshell and an overhead trellis of speakers extending into the lawn, hosts the Grant Park Music Festival and dozens of free concerts throughout the summer. The Lurie Garden, a beautifully planted public garden occupying five acres at the southern end of Millennium Park, is a triumph of landscape design that draws visitors year-round.
Buckingham Fountain at the center of Grant Park is one of the most beautiful public fountains in the world, a massive Beaux-Arts structure modeled on the Latona Fountain at Versailles and operating with hourly light and water shows from May through October.
The Magnificent Mile and the Near North Side
Michigan Avenue north of the Chicago River, known as the Magnificent Mile, is Chicago’s premier shopping and hotel corridor, lined with flagship stores from major American and international retailers, luxury hotels, and some of the city’s most important architectural landmarks. The Tribune Tower, completed in 1925 in Gothic Revival style, contains embedded fragments of famous buildings and monuments from around the world pressed into its base. The Wrigley Building, its gleaming white terra-cotta twin towers flanking the river at the south end of the Mag Mile, is one of the most beautiful commercial buildings in Chicago. The John Hancock Center, now formally known as 875 North Michigan Avenue, rises dramatically at the northern end of the Mag Mile and offers panoramic views from its observation deck and its top-floor bar.
The Water Tower and Pumping Station, survivors of the Great Chicago Fire of 1871 and beloved landmarks of the Near North Side, stand amid the retail density of Michigan Avenue as reminders of the city’s pre-fire history.
The Newberry Library, a short walk west of Michigan Avenue, is one of the great independent research libraries in the United States, with extraordinary collections in the humanities and a public program of exhibitions, lectures, and events. The Moody Church and the Fourth Presbyterian Church, both near the Mag Mile, are architecturally significant religious buildings worth a detour.
River North
River North, the neighborhood immediately north of the Chicago River and west of Michigan Avenue, is one of the most densely concentrated gallery districts in the United States, with dozens of commercial art galleries occupying the loft spaces of former warehouses along Superior, Huron, and Erie Streets. The neighborhood is also home to some of Chicago’s best restaurants and a vibrant nightlife scene, and the conversion of its industrial buildings into restaurants, clubs, and creative spaces has made it one of the most economically dynamic neighborhoods in the city.
Gold Coast and Streeterville
The Gold Coast, along the lakefront north of the Magnificent Mile, is one of the wealthiest urban residential neighborhoods in the United States, lined with magnificent mansion architecture from the late nineteenth and early twentieth centuries alongside luxury high-rise apartment buildings. The neighborhood’s retail along Rush Street and Oak Street includes some of the finest boutique shopping in the city. Oak Street Beach, at the foot of the neighborhood’s lakefront, is one of the most urban and dramatic beach settings in the country, with the skyline rising immediately behind the sand.
Streeterville, east of Michigan Avenue near the lake, contains Northwestern University’s Chicago campus, several of the city’s major hospitals, and the Museum of Contemporary Art Chicago, one of the finest contemporary art museums in the United States.
Lincoln Park
Lincoln Park is one of Chicago’s most beloved and livable neighborhoods, a long stretch of residential streets, restaurants, bars, boutiques, and parks running along the lakefront north of the Near North Side. The neighborhood takes its name from the enormous park that borders it to the east, one of the finest urban parks in the country. Lincoln Park Zoo, within the park, is one of the last free admission zoos in the United States and one of the finest of its size anywhere, with excellent habitats for gorillas, polar bears, big cats, and hundreds of other species. The Lincoln Park Conservatory, an ornate Victorian greenhouse adjacent to the zoo, houses palm trees, ferns, and exotic plants year-round and is a welcome refuge in the winter months.
Armitage Avenue and Halsted Street within the neighborhood offer excellent independent shopping, dining, and cafe culture. The neighborhood’s farmers market, theater companies, and active community life make it one of the most complete urban neighborhoods in Chicago.
Wicker Park and Bucktown
Wicker Park and Bucktown, just northwest of downtown, are neighboring areas that have evolved from working-class immigrant communities through an arts-and-music counterculture phase in the 1980s and 1990s into one of the most fashionable and expensive residential neighborhoods in Chicago, while retaining more of their original character and independent spirit than many similarly gentrified urban neighborhoods. Milwaukee Avenue, the diagonal street cutting through the neighborhood, is lined with independent restaurants, bars, coffee shops, vintage clothing stores, and music venues that reflect the area’s creative heritage.
The Flat Iron Arts Building and the nearby Wicker Park neighborhood house is a concentration of artists’ studios and gallery spaces. The Double Door, Empty Bottle, and Subterranean are among the most important independent music venues in Chicago, hosting a mix of local and national acts across virtually every genre. The Green Mill cocktail lounge in the Uptown neighborhood nearby, a legendary jazz club that dates to the Prohibition era and was a frequent haunt of Al Capone, offers live jazz seven nights a week in one of the most atmospheric bar environments in the city.
Pilsen and the Lower West Side
Pilsen is one of Chicago’s most culturally vibrant and visually striking neighborhoods, a historically Mexican-American community on the Lower West Side whose streets are covered in extraordinary murals and whose restaurants, bakeries, and tortillerias offer some of the finest and most authentic Mexican food in a city with remarkable Mexican culinary depth. The neighborhood has attracted artists, galleries, and creative businesses alongside its established community institutions, and the tension and energy produced by that coexistence gives Pilsen a particular dynamism.
The National Museum of Mexican Art in Pilsen is the largest Latino cultural institution in the United States and one of the finest art museums in Chicago, with a permanent collection of over ten thousand works spanning pre-Columbian to contemporary Mexican and Mexican-American art and a dynamic program of changing exhibitions and community events. Admission is free.
The 18th Street business corridor is the heart of Pilsen’s commercial life, lined with taquerias, panaderias, restaurants, bars, and shops. The Damen Avenue strip of galleries and independent businesses reflects the neighborhood’s artistic dimension. The Pilsen Murals Project has produced dozens of large-scale works covering building walls throughout the neighborhood that constitute one of the finest open-air public art collections in the city.
Bronzeville and the South Side
Bronzeville, on Chicago’s South Side, is one of the most historically significant African-American neighborhoods in the United States, the destination for hundreds of thousands of Black migrants from the American South during the Great Migration of the early to mid-twentieth century and the birthplace of a cultural flowering in music, literature, journalism, and civic life that produced figures including Ida B. Wells, Gwendolyn Brooks, Richard Wright, and Louis Armstrong. The neighborhood’s architectural heritage includes magnificent churches, greystone apartment buildings, and the elegant homes of the Black professional class that established itself here during the decades of segregation.
The DuSable Black History Museum and Education Center, named for Jean Baptiste Point DuSable, the Haitian-born fur trader who established the first permanent settlement at the site of what would become Chicago, is one of the most important African-American history museums in the United States, with a collection of over 15,000 objects documenting the history, culture, and achievements of Black Americans.
Hyde Park, further south along the lakefront, is the home of the University of Chicago, one of the great research universities in the world, and its campus of Gothic Revival stone buildings and beautifully maintained green spaces is one of the finest academic environments in the country. The Barack Obama Presidential Center, currently under construction in Jackson Park adjacent to Hyde Park, will be one of the most significant new cultural institutions in Chicago when it opens.
Andersonville and Rogers Park
Andersonville, on the far North Side, is a neighborhood of Swedish heritage that has evolved into one of Chicago’s most welcoming and LGBTQ-friendly communities, with an excellent concentration of independent restaurants, coffee shops, bookstores, and bars along Clark Street. Women and Children First, a feminist bookstore operating since 1979, is one of the most important independent bookstores in Chicago. The neighborhood’s Swedish-American heritage is celebrated at the Swedish-American Museum, a small and charming institution documenting the community’s history and cultural contributions.
Rogers Park, at the northernmost tip of the city on the Lake Michigan shore, is one of the most racially and economically diverse neighborhoods in Chicago, with a large immigrant population from Ethiopia, Ghana, West Africa, Mexico, and many other origins coexisting with students from Loyola University, long-time residents, and a growing creative community. Its lakefront, accessible at several points, has a more intimate and less developed character than the lakefront further south.
Major Attractions and Museums
The Art Institute of Chicago
The Art Institute of Chicago is one of the greatest art museums in the world and the crown jewel of Chicago’s extraordinary cultural infrastructure. Founded in 1879 and housed in a magnificent Beaux-Arts building on Michigan Avenue at the edge of Grant Park, with a major Modern Wing addition designed by Renzo Piano opened in 2009, the museum contains a collection of over 300,000 works spanning five thousand years of human artistic production across every medium and culture.
The Impressionist and Post-Impressionist collection is one of the finest outside of Paris, with iconic works including Georges Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, and Pablo Picasso’s The Old Guitarist among its most celebrated holdings. The American art collection, the Asian art galleries, the medieval European collection, the textiles department, the photography collection, and the architecture and design holdings are all of exceptional quality and depth. The museum’s restaurant, Terzo Piano, in the Modern Wing is one of the finest museum dining experiences in any American institution. Visiting the Art Institute is an essential Chicago experience and one of the finest museum days available anywhere in the United States.
The Field Museum
The Field Museum of Natural History on the Museum Campus south of Grant Park is one of the great natural history museums in the world, with a collection of over 24 million specimens and objects spanning geological, biological, anthropological, and cultural history across the full breadth of life on Earth. The museum’s centerpiece is Sue, the largest, most complete, and best-preserved Tyrannosaurus rex skeleton ever discovered, displayed in the main Stanley Field Hall in a pose of breathtaking scale and presence. The museum’s permanent exhibitions cover Ancient Egypt, Native American cultures of the Pacific Northwest and the Great Plains, the geological history of the Earth, the ecosystems of Africa, and dozens of other subjects with depth and scholarly rigor that rewards repeated visits.
The Shedd Aquarium
The John G. Shedd Aquarium, also on the Museum Campus, is one of the finest indoor aquariums in the world and one of the most beloved institutions in Chicago. Its collection of over 32,000 animals includes beluga whales, Pacific white-sided dolphins, sharks, sea otters, penguins, and an extraordinary diversity of fish, invertebrates, amphibians, and reptiles. The Caribbean Reef exhibit, where divers interact with the inhabitants of a 90,000-gallon reef tank during feeding demonstrations, is one of the most popular attractions in the city. The Wild Reef exhibit recreates a Philippine coral reef environment with exceptional naturalism.
The Adler Planetarium
The Adler Planetarium, the third institution of the Museum Campus, is the oldest planetarium in the Western Hemisphere and one of the finest in the world. Its sky shows, astronomy exhibitions, and genuine research mission combine to make it one of the most substantive and engaging science institutions in Chicago. The planetarium’s position at the tip of a peninsula jutting into Lake Michigan also provides one of the finest panoramic views of the Chicago skyline available anywhere, and the lakefront walk around the Museum Campus offers spectacular vistas in all directions.
The Museum of Science and Industry
The Museum of Science and Industry, located in Hyde Park in a magnificent building originally constructed as the Palace of Fine Arts for the 1893 World’s Columbian Exposition, is one of the largest science museums in the Western Hemisphere and one of the most engaging and interactive science institutions in the country. Its collection includes a genuine German U-boat submarine captured during World War Two, a full-scale reproduction of a working coal mine, a Boeing 727 suspended from the ceiling, a simulated space mission, and hundreds of interactive exhibits covering every domain of science and technology. It is one of the finest family destinations in Chicago and genuinely absorbing for adult visitors as well.
The Chicago History Museum
The Chicago History Museum, in a handsome building at the south end of Lincoln Park, is the definitive institution for understanding the history of Chicago and Illinois. Its collections span the full range of the city’s extraordinary history, from the Fort Dearborn era through the Great Fire, the World’s Columbian Exposition, the Jazz Age, the civil rights movement, and the political upheavals of the late twentieth century. The museum holds Abraham Lincoln’s deathbed, an original copy of the Emancipation Proclamation, and the first locomotive to operate in Chicago, alongside thousands of photographs, documents, and objects illuminating the lives of ordinary Chicagoans across the city’s history.
Architecture
Chicago’s relationship with architecture is unlike that of any other city in the world. The destruction of the Great Fire created a blank slate on which the architects of the Chicago School, working in the last two decades of the nineteenth century, invented the modern skyscraper and established principles of structural logic, ornamental restraint, and functional expression that transformed the built environment of cities globally.
The subsequent century of building in Chicago produced a skyline that is simultaneously one of the most beautiful and one of the most architecturally significant in the world, a living museum of the history of modern architecture in which buildings by Louis Sullivan, Daniel Burnham, Mies van der Rohe, Skidmore Owings and Merrill, Helmut Jahn, Renzo Piano, Jeanne Gang, and dozens of other pivotal figures stand in conversation with one another across a remarkably compact geography.
The Chicago Architecture Center on the Chicago Riverwalk is the essential starting point for architectural exploration. Its exhibition space presents the history and significance of Chicago’s built environment with exceptional clarity and depth, and it operates the finest selection of architecture tours available in the city, including the celebrated river tours aboard glass-topped boats that provide views of the skyline from the water and expert commentary from knowledgeable docents. Walking tours of the Loop, the lakefront, and specific neighborhoods are also available and are among the finest educational experiences available to visitors in Chicago.
Among the most significant individual buildings, the Rookery Building of 1888, with its extraordinary light court redesigned by Frank Lloyd Wright in 1905, is one of the most beautiful interior spaces in Chicago. The Auditorium Building by Adler and Sullivan is a masterpiece of acoustic and structural engineering. The Monadnock Building is the tallest load-bearing masonry structure ever built. The Carson Pirie Scott building, now Sullivan Center, displays Louis Sullivan’s ornamental genius in its cast-iron entrance surround. The Reliance Building, now the Burnham Hotel, anticipated the glass-curtain-wall skyscraper by sixty years. Mies van der Rohe’s Illinois Institute of Technology campus on the South Side and his 860-880 Lake Shore Drive apartment towers are monuments of International Style modernism. The John Hancock Center, the Willis Tower formerly Sears Tower, and the Aqua Tower by Jeanne Gang represent successive generations of Chicago’s continued architectural ambition.
Frank Lloyd Wright’s influence is also profound in the Chicago region. His studio and home in the suburb of Oak Park, a short L ride from downtown, is a pilgrimage site for architecture enthusiasts, and the surrounding neighborhood contains the largest concentration of Wright-designed buildings in the world. The Robie House in Hyde Park near the University of Chicago is his masterpiece of the Prairie Style and one of the most important domestic buildings in American architectural history.
Food and Dining
Chicago’s food culture is one of the richest and most diverse in the United States, a reflection of the city’s extraordinary immigrant history, its agricultural heartland context, its blue-collar culinary traditions, and its increasingly sophisticated and nationally recognized fine dining scene.
The deep dish pizza is Chicago’s most famous culinary export and a subject of genuine civic pride and occasional defensiveness. Deep dish is a casserole-style pizza baked in a high-sided pan, with a thick buttery crust, layers of cheese and toppings beneath a thick layer of chunky tomato sauce, requiring forty-five minutes or more of baking time. Lou Malnati’s, Giordano’s, Gino’s East, and Pequod’s are the most beloved deep dish institutions, each with devoted partisans and genuine differences in crust style, sauce character, and ingredient quality. Pequod’s caramelized cheese crust is a particular cult favorite. It is worth noting that Chicagoans themselves frequently eat thin-crust tavern-style pizza, cut into squares rather than wedges, with equal enthusiasm, and the thin-crust offerings at places like Vito and Nick’s and Marie’s Pizza are as authentically Chicago as the deep dish variety.
The Chicago-style hot dog is another canonical local food, a beef frankfurter in a poppy seed bun topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, sport peppers, and celery salt. The absolute prohibition against ketchup on a Chicago hot dog is one of the city’s most earnestly held culinary convictions. Vienna Beef is the historic producer of the authentic Chicago hot dog, and dozens of venerable hot dog stands throughout the city, including Gene and Jude’s in River Grove and the Wieners Circle in Lincoln Park, serve them with the institutional confidence of places that have been doing one thing perfectly for decades.
The Italian beef sandwich, another Chicago original, is thinly sliced seasoned roast beef piled onto a long Italian roll and dipped into the savory cooking jus, with the option of sweet or hot giardiniera peppers. Al’s Beef, Portillo’s, and Mr. Beef on Orleans are among the most celebrated purveyors. Eating an Italian beef sandwich correctly involves getting it dunked, accepting the inevitable dripping, and consuming it with the unselfconscious pleasure of someone who is not thinking about their clothes.
Beyond these iconic local specialties, Chicago’s dining landscape is extraordinarily diverse and increasingly celebrated at the national and international level. The city has produced some of the most influential chefs and restaurants in American culinary history. Alinea, Grant Achatz’s three-Michelin-starred temple of avant-garde gastronomy in Lincoln Park, is consistently ranked among the finest restaurants in the world, presenting multicourse tasting menus that challenge the fundamental assumptions of what eating in a restaurant can be. The Publican in Fulton Market is one of the most celebrated gastropubs in the country, with an emphasis on whole animal butchery, house-cured charcuterie, exceptional oysters, and a beer list of extraordinary depth. Girl and the Goat by Stephanie Izard is another Fulton Market landmark, consistently one of the most vibrant and delicious restaurants in the city. Smyth and the Loyalist in the West Loop offer exceptional fine dining and casual dining respectively from chef John Shields and Karen Urie Shields.
The restaurant landscape of Chicago’s immigrant communities is perhaps the most underappreciated aspect of the city’s food culture by outside visitors. Chinatown on the South Side, centered around Cermak Road and Wentworth Avenue, is one of the most vibrant and authentic Chinatown districts in the United States, with excellent Cantonese, Sichuan, Hong Kong-style, and dim sum restaurants. Devon Avenue on the far North Side is one of the most remarkable ethnic restaurant corridors in the country, where Indian, Pakistani, Afghan, and Middle Eastern restaurants succeed one another for blocks. Pilsen and Little Village on the Southwest Side offer the finest Mexican food in a city with extraordinary Mexican culinary depth. Argyle Street in Uptown is the center of the Vietnamese community with excellent pho and other Southeast Asian restaurants. The Ethiopian restaurants of Rogers Park and Edgewater are outstanding.
The craft beer scene in Chicago is rich and well-developed, with dozens of breweries operating across the city and suburbs. Goose Island Beer Company, founded in Chicago in 1988 and now nationally distributed, pioneered craft brewing in the city. Revolution Brewing, Half Acre Beer Company, Dovetail Brewery, and Maplewood Brewery are among the most respected independent craft breweries currently operating in the city. The craft cocktail scene is equally sophisticated, with excellent bars in virtually every neighborhood.
Music
Chicago’s contribution to American music is almost impossible to overstate. The city is the birthplace of the electric blues, the genre that directly shaped rock and roll and therefore the entire landscape of popular music in the second half of the twentieth century. Muddy Waters, Howlin Wolf, Little Walter, Buddy Guy, Otis Rush, and dozens of other artists who migrated from the Mississippi Delta and the American South brought the blues to Chicago and transformed it in the city’s noisy, electric environment into something harder, louder, and more urgent. That music traveled to England in the early 1960s, where it ignited the Rolling Stones, the Yardbirds, and Led Zeppelin, and from there it changed the world.
Buddy Guy’s Legends on South Wabash Avenue is the most important blues club in Chicago, operated by the legendary guitarist himself, and features live blues performances seven nights a week. SPACE in Evanston and the Hideout in Bucktown are among the finest small music venues in the city for a broader range of Americana, folk, country, and alternative music.
Chicago is also the birthplace of house music, the electronic dance music genre that emerged from the city’s Black and Latino gay club culture in the early 1980s, particularly from the legendary Warehouse club whose DJ Frankie Knuckles became one of the founding figures of the genre. House music spread from Chicago to the world and remains one of the most globally influential American musical exports of the late twentieth century.
The Chicago Symphony Orchestra, one of the five great American orchestras and among the finest in the world, performs at Orchestra Hall, a magnificent 1904 building on Michigan Avenue that is one of the finest concert venues in the United States. The Lyric Opera of Chicago is one of the three major opera companies in the country. The Chicago Jazz Festival, held free of charge in Millennium Park and the Cultural Center each Labor Day weekend, is one of the premier outdoor jazz events in the United States.
The city’s live music venue ecosystem, from the enormous United Center and Wrigley Field for the largest touring acts to intimate clubs in Wicker Park, Logan Square, and Pilsen, is one of the richest and most diverse of any American city.
Comedy
Chicago is the capital of American improv comedy, the city where the form was pioneered in the 1950s and where the institutions that have trained the majority of the country’s working comedians continue to operate with extraordinary vitality. The Second City comedy club on North Wells Street in Old Town has been the most important institution in American comedy for over sixty years, the training ground for generations of performers including John Belushi, Bill Murray, Gilda Radner, Harold Ramis, Tina Fey, Stephen Colbert, Steve Carell, Amy Poehler, and hundreds of others whose work has defined American comedy. Second City presents multiple shows nightly on its main stage and e.t.c. stage, mixing scripted sketch comedy with improvised scenes in the tradition the company has refined over six decades. Visiting Second City is one of the finest and most distinctly Chicago entertainment experiences available.
iO Theater, also in Lincoln Park, is the other pillar of the Chicago improv scene, founded by Del Close and Charna Halpern and the originator of the long-form improv format known as the Harold. The Annoyance Theatre and ComedySports round out a comedy ecosystem of remarkable depth and quality.
Sports
Chicago is one of the great sports cities in the United States, with passionate and knowledgeable fan bases for all of its major professional franchises and two of the most historic and beloved ballparks in the country.
Wrigley Field, the home of the Chicago Cubs, opened in 1914 and is the second-oldest ballpark in Major League Baseball, a beloved ivy-covered brick structure on the North Side of the city that has become one of the most iconic sports venues in America. Attending a game at Wrigley, with its rooftop bleachers on the buildings beyond the outfield walls, its hand-operated scoreboard, and its intensely loyal fan community, is one of the finest sports experiences in Chicago regardless of one’s baseball allegiance. The Cubs ended their 108-year World Series championship drought in 2016, winning the championship in a Game 7 for the ages.
Guaranteed Rate Field, formerly Comiskey Park, is the home of the Chicago White Sox on the South Side, a more modern facility with a different but equally devoted fan base. The White Sox won the World Series in 2005.
The Chicago Bulls, winners of six NBA championships in the 1990s in the era of Michael Jordan, Scottie Pippen, and Phil Jackson, play at the United Center on the West Side, which they share with the Chicago Blackhawks of the NHL. The Blackhawks won three Stanley Cup championships between 2010 and 2015 in one of the most dominant runs in recent hockey history. The United Center is also one of the premier concert venues in the Midwest.
The Chicago Bears of the NFL are one of the oldest and most storied franchises in professional football, and while they have been rebuilding for several seasons they retain a massive and passionate fan base. They play at Soldier Field on the lakefront adjacent to the Museum Campus, a peculiar but historically significant building with a classical colonnade wrapped around a modernized interior.
Festivals and Events
Chicago’s calendar of festivals and public events is one of the richest of any American city, reflecting both the city’s cultural diversity and its commitment to free and accessible public programming.
The Chicago Blues Festival, held each June in Millennium Park and the surrounding Grant Park area, is the largest free blues festival in the world, drawing hundreds of thousands of attendees over three days for performances across multiple stages by the greatest living blues artists alongside emerging talent.
The Chicago Jazz Festival at Labor Day weekend, also free in Grant Park, is one of the premier outdoor jazz events in the country. The Grant Park Music Festival presents free classical concerts throughout the summer at the Jay Pritzker Pavilion, one of the finest outdoor classical music settings in America. The Chicago Folk and Roots Festival in Wicker Park’s Holstein Park in July is a beloved community festival with an excellent lineup.
Lollapalooza, the massive multi-day music festival held each August in Grant Park, transforms the lakefront park into one of the largest music events in the country, drawing over 100,000 people per day for a lineup that spans virtually every genre of popular music.
The Chicago Air and Water Show, held each August along the North Side lakefront between North Avenue Beach and Oak Street Beach, is the largest free air show in the United States, drawing enormous crowds to watch military and civilian aerobatics above the lake. The Chicago Marathon in October is one of the six World Marathon Majors, attracting elite runners from around the world and tens of thousands of recreational participants through a course that passes through dozens of Chicago neighborhoods.
The Taste of Chicago, a massive food festival in Grant Park in July, showcases dozens of Chicago restaurants across multiple days of eating, entertainment, and lakefront celebration.
Parks and the Lakefront
Chicago’s lakefront is its greatest civic achievement, and the fact that the entire twenty-six miles of Lake Michigan shoreline within the city limits is publicly accessible parkland, with no private development blocking the view or the access, is the result of deliberate policy choices stretching back to the nineteenth century and the vision of landscape architect Daniel Burnham’s 1909 Plan of Chicago.
The lakefront trail connects the entire length of Chicago’s lakefront and is one of the finest urban recreational paths in the United States, used year-round by runners, cyclists, rollerbladers, and walkers. The beaches along the lakefront, including Oak Street Beach, North Avenue Beach, Montrose Beach, and dozens of others, are beautiful, well-maintained, and free. Lake Michigan, despite its inland location, behaves like a sea, with waves, currents, and weather systems that make it genuinely dramatic and occasionally dangerous. Swimming is excellent in summer when the water warms sufficiently, and the beaches are packed with Chicago residents taking full advantage of their extraordinary lakefront.
Lincoln Park, Grant Park, Millennium Park, Humboldt Park, Washington Park, Jackson Park, and dozens of neighborhood parks throughout the city provide green space, recreation, and community gathering places for residents across the city. The 606, a elevated trail converted from a former rail line through Wicker Park, Bucktown, Logan Square, and Humboldt Park, is one of the finest examples of the rail trail conversion model that has transformed post-industrial infrastructure into beloved public amenities in cities around the world.
Day Trips from Chicago
Chicago’s central location and excellent transportation connections make it an ideal base for day trips to a remarkable range of destinations.
Evanston, immediately north of Chicago and accessible by CTA Purple Line or Metra, is a beautiful lakefront university town, home to Northwestern University, with excellent independent restaurants, bookstores, and lakefront access.
Oak Park, accessible by CTA Green Line, is the birthplace of Ernest Hemingway and the location of Frank Lloyd Wright’s home and studio alongside the world’s largest concentration of Wright-designed buildings. The combination of literary and architectural significance makes it one of the finest day trips from Chicago.
The Indiana Dunes National Park, about an hour east of Chicago on the southern shore of Lake Michigan, is a stunning natural landscape of massive sand dunes, beaches, and diverse ecosystems that represents one of the most ecologically varied national parks in the country. Swimming, hiking, and dune climbing are the primary activities.
Galena, in the far northwestern corner of Illinois about three hours by road from Chicago, is a beautifully preserved nineteenth century town with excellent architecture, independent shops, and the former home of Ulysses S. Grant. The rolling hills of Jo Daviess County surrounding it offer beautiful scenery distinct from the flat prairie that characterizes most of Illinois.
Milwaukee, Wisconsin, about ninety minutes north by road or Amtrak Hiawatha service, is a city with excellent museums including the magnificent Milwaukee Art Museum, a strong craft beer culture rooted in its German-American heritage, and a lively and affordable dining and nightlife scene.
Practical Information
Climate: Chicago has a continental climate of genuine extremes that should not be underestimated. Winters are cold, with temperatures frequently dropping below zero Fahrenheit with wind chill, and snowfall that can be substantial. Lake-effect snow from Lake Michigan can produce significant accumulations with little warning. Summers are warm to hot, with temperatures in the mid-eighties to low nineties Fahrenheit and humidity that can make the heat feel more intense than the thermometer indicates. The finest weather occurs in May, June, September, and October, when temperatures are mild, the lakefront is beautiful, and the city’s outdoor life is in full expression. July and August are the peak tourist months, bringing the largest crowds and the most active festival calendar alongside the warmest weather.
Safety: Chicago is a large and complex city with significant variation in safety between neighborhoods. The areas most visited by tourists, including the Loop, the Magnificent Mile, River North, Lincoln Park, Wicker Park, and the lakefront, are generally very safe. Visitors should exercise the standard urban common sense of any major American city, be aware of their surroundings, and consult local knowledge or current resources about specific areas they plan to visit.
Getting the Most from the City: Chicago rewards the visitor who ventures beyond the major museum campus and the Magnificent Mile into the neighborhoods. The city’s neighborhood life, its restaurants, its music venues, its community institutions, and its street character are where the most authentic and memorable experiences are often found. Using the L to explore is both practical and revealing, offering an elevated perspective on the city’s geography and character that no other mode of transit can provide.
Costs: Chicago is significantly more affordable than comparable coastal cities, particularly for accommodation, dining, and entertainment. Excellent meals are available at every price point, and the city’s extraordinary collection of free cultural institutions, including the Art Institute on certain evenings, the Museum of Science and Industry on select days, the Field Museum, and many smaller museums with free admission policies, makes a rich cultural experience accessible at relatively modest cost.
Conclusion
Chicago earns its greatness the hard way, not through scenery or climate or geography that nature handed it as a gift, but through the accumulated effort, ambition, creativity, and resilience of the people who built it and continue to build it. The lakefront is magnificent but it was made magnificent by deliberate choice. The architecture is extraordinary but it was created by human vision applied to the specific challenges and opportunities of this place. The music, the food, the comedy, the literature that Chicago has given the world all emerged from the specific conditions of a specific city, its immigrant communities, its industrial economy, its racial history, its weather, its pride.
That is what makes Chicago, finally, so moving to visit. It is a city that made itself, that decided it was going to be great and then went about the serious business of being great with a thoroughness and a lack of pretension that are entirely characteristic. It does not perform its greatness for visitors. It is simply great, and it invites you to discover that for yourself, neighborhood by neighborhood, meal by meal, musical note by architectural detail, along the magnificent shore of its incomparable lake.
