A cultural guide to Chicago
America’s “Second City” is first class for architecture, comedy, art, and food—from fine dining to (of course) deep-dish pizza
Your essential guide to the best things to see and do in Chicago. Find more travel inspiration for more amazing cities here.
Chicago’s soaring steel skyscrapers rise from the edge of the seemingly infinite blue expanse of Lake Michigan; a patchwork of diverse neighborhoods unfurls beyond them. It all started with a Black trader named Jean Baptiste Point du Sable, the area’s first non-native settler, who arrived in 1779. Soon, it grew into the “City of the Big Shoulders,” a nickname coined by poet Carl Sandburg in tribute to the working-class grit that transformed a swampy patch of prairie into a magnificent cluster of glass and steel towers.
Today, America’s “Second City” still teeters between blue-collar modesty and great aspirations, a tension played out in its innovative but accessible dining scene, its genre-defining comedy style, and even the functional-meets-elegant architecture that fills its skyline. Peel away the layers here and you’ll discover a buzzing creative energy, and a bold authenticity that’s made Chicago one of the most American of American cities.
Art & architecture
The Art Institute of Chicago is the city’s most-visited museum, thanks to its hit list of greats like Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, and one of the world’s largest collections of impressionist art. The city’s Museum of Contemporary Art, meanwhile, champions “the new and unexpected”—think Jasper Johns, Kerry James Marshall, and Cindy Sherman. Walk through verdant Millennium Park to view Anish Kapoor’s famed Cloud Gate aka “the Bean” (pictured top). Save time for gallery hopping: Pilsen (Woman Made, Vault Gallerie), Bridgeport (Morgan Arts Complex, Bridgeport Art Center), and West Town (Rhona Hoffman, PATRON) are the districts to know.
Chicago is the birthplace of the modern skyscraper, and the city’s super-popular Architecture River Cruise is a great way to learn more about its groundbreaking building design. You’ll motor along downtown’s urban “canyon,” flanked by heavy hitters like the Wrigley Building, Lyric Opera House, and Willis Tower (the world’s tallest until 1998). Or for something a little more ornate, Chicago Cultural Center is home to the world’s largest Tiffany glass dome, with 30,000 pieces of glass cut in the shape of fish scales, topped with the signs of the zodiac.
Expert tips
The essentials
O’Hare International Airport is Chicago’s sprawling main airport. Smaller Midway services almost exclusively North American destinations. The CTA trains in Chicago are known as “L” trains. From Midway, take the Orange Line to downtown in 20–25 minutes. The Blue Line connects O’Hare to downtown in 40–45 minutes. Trains run 24 hours a day.
Getting around
Contactless card payments are taken on CTA trains and buses, while yellow cabs accept credit card payments with no minimum fare. Chicago is a walkable city and the grid system is easy to navigate. For an alternative mode of transport, take a water taxi along the Chicago River from mid-March to late November. Buy tickets with cash or card at the dock.
Accessibility
All CTA buses are wheelchair-accessible; 70% of train stations are accessible. Note that elevator services can also be unreliable, so check before traveling. The Goodman Theatre offers audio descriptions for all its regular productions.
LGBTQ+
Chicago’s LGBTQ+ scene centers around Boystown (recently rebranded as Northalsted to be more inclusive). Uptown, Edgewater, and Rogers Park are also key neighborhoods. Chicago’s Pride Month celebrations kick off in June, culminating in a two-day Pride Fest and parade. If you miss it, the Northalsted Market Days festival is in August.
Family
Chicago’s museum scene makes it a great destination for families. Start at the city’s lakefront Museum Campus to explore multiple institutions in one place, including The Field Museum, the Shedd Aquarium, and the Adler Planetarium. Meanwhile, Navy Pier is home to the interactive Chicago Children’s Museum (and the city’s famed Ferris wheel). Further south, the Museum of Science & Industry offers hands-on, whizbang exhibits. And Millennium Park, with its climbing wall, seasonal ice-skating rinks and playgrounds, is another can’t-miss for families. Kids under seven ride CTA trains and buses for free.
Food & drink
Chicago is home to nearly two dozen Michelin-starred restaurants, but where the city really excels is in casual and mid-range dining. Mexican food in particular shines here—from fast and friendly storefront taquerias to sophisticated regional takes like Mi Tocaya in Logan Square and 5 Rabanitos in Pilsen, near the formidable National Museum of Mexican Art.
For lunch, dig into irresistible casual eats like an Italian-beef sandwich from Mr. Beef, which inspired the Hulu series The Bear. For an authentic Chicago hot dog, late-night favorite The Wiener’s Circle in Lincoln Park serves comical insults (and the occasional celebrity sighting) with your order. If your curiosity for deep-dish pizza must be sated, Pizano’s makes a fine pie, while Pizzeria Uno is the original; both are downtown.
Many of the city’s top restaurants are clustered around Randolph Street, a.k.a. Restaurant Row. There, you’ll find Girl & The Goat from Top Chef winner Stephanie Izard, as well as Monteverde for Italian, Oriole for its two-star Michelin tasting menu, and many more. In Lincoln Park, the city’s most famous restaurant, Alinea, offers an immersive modernist experience, but reservations are scarce.
Music
There are plenty of sounds to be soaked up in this city: Take your pick from small-but-iconic rock venues like Metro, Empty Bottle, and Thalia Hall, or hit one of the famous festivals, including Lollapalooza in August.
Throughout the summer, free lakefront fests bring blues, jazz and gospel to the masses; travelers and locals alike adore the intimate Green Mill lounge for jazz and Buddy Guy’s for blues.
Hot ticket
The Second City comedy club has likely churned out more comedic stars than any other. Since opening in 1959, the sketch and improv club has launched the careers of big film and TV names such as Steve Carrell, Tina Fey, Eugene Levy, and more. To catch the best talent, book a Mainstage or e.t.c. show (there are seven stages in all). Stay late for the free improv set offered after most performances.
Eugene Levy: “It’s never too late to travel”
Most hotels are located downtown, also known as The Loop. From there, you can easily access the Riverwalk, museums, Magnificent Mile shops and Millennium Park’s Anish Kapoor sculpture nicknamed “The Bean.” One of the more intriguing places to stay is the Chicago Athletic Association hotel, housed in a reimagined 1893 athletic club; head to the rooftop for Cindy’s bar, eatery and terrace, which overlooks Millennium Park and the lake.
Away from downtown’s bustle, leafy Lincoln Park stuns with its expansive lakefront park and trail (perfect for jogging or biking), a free zoo, lively North Avenue Beach, and several museums. Stay at Hotel Lincoln and pop up to the rooftop for gorgeous views.
Northwest of downtown, Milwaukee Avenue runs through the trendy Wicker Park and Logan Square neighborhoods, offering great restaurants, bars and shops. Stay in the heart of the action at The Robey, housed in an art-deco former office building, with a seasonal rooftop pool and bar offering skyline views.
Martina Sheehan is a Chicago-based travel writer-editor who has written for the New York Times, Condé Nast Traveler, Budget Travel, Forbes Travel Guides, and Time Out guidebooks, among others. She has traveled to 38 countries and 46 states, and never leaves home without a good map app, a themed playlist, and her daughter.
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