Discover music and theater in Chicago, from Broadway shows to live outdoor concerts

Skirting the shore of Lake Michigan, Chicago is known for its standout architecture, vibrant cultural institutions, and delicious food, from Michelin-starred fine dining to deep-dish pizza. The city’s eye-catching skyline includes the soaring Willis Tower, where glass boxes jut out from the Skydeck, allowing you to peer down more than a quarter of a mile to the street below. A stroll along the Chicago Riverwalk takes you past buzzing patio eateries and quirky public art, while the lakefront Art Institute of Chicago offers works by van Gogh and Picasso. From there, stroll through Grant Park to reach Museum Campus, a sprawling green space home to beluga whales at the Shedd Aquarium and a T-Rex fossil skeleton at the Field Museum. Cozy live music venues draw renowned jazz and blues musicians, and the city’s theater district is famed for its groundbreaking productions. If you’re here to shop, Michigan Avenue’s Magnificent Mile has it all: department stores, chic boutiques, and malls with every chain imaginable.

Reasons to go:

• Plays and musicals: The hottest shows from Broadway inevitably make debuts at Chicago venues like the CIBC Theatre, an opulent 1906 auditorium that’s hosted productions from Carousel to Hamilton. For a more intimate experience, catch cutting-edge contemporary drama in A Red Orchid Theatre, a cozy 70-seat theater in Old Town.

• Live outdoor gigs: From June through August, the Grant Park Music Festival hosts both big-name and up-and-coming artists for free concerts beneath the gleaming Frank Gehry-designed bandshell in Millennium Park. Expect everything from indie rock to jazz guitar and Latin American beats. Held in leafy parkland north of the city, Ravinia Festival is the oldest outdoor music festival in the US and hosts an eclectic summer-long series that includes a seasonal residency by the Chicago Symphony Orchestra.

• Sugary desserts: Whether your deep-dish pizza preferences lean toward Giordano’s or Lou Malnati’s, locals agree that Bang Bang Pie & Biscuits is a top spot for sweet pies like the key lime and the spiced pumpkin. At Floriole Café & Bakery, you can snack on scrumptious pastries from classics such as sticky buns or pain au chocolat to the chef-owner’s famous passionfruit tart.

• River boating: Gaze up at colossal skyscrapers as Urban Kayaks takes you on a guided paddle tour of the Chicago River. Weekend twilight tours take in Art on theMART, a striking installation of illuminated images projected against the facade of the art deco Merchandise Mart building. If you’d rather party than paddle, cruise aboard the Island Party Boat, a floating tiki bar.

• Chicago Arts District: Check out contemporary art and meet local artists on 2nd Fridays, a monthly gallery night in the hip Pilsen neighborhood. Colorful murals reflect the district’s Mexican heritage, and the National Museum of Mexican Art covers more than 3,000 years of culture, from paintings and photography to traditional textiles. Refuel with fish tacos or carnitas at one of the area’s many laid-back taquerias.

When to go

Summers in Chicago are warm, and daytime winter highs usually hover around freezing. Visit May through October to see the city come alive with runners and cyclists, or join winter revelers for a glide on outdoor ice-skating rinks like the winding skating ribbon in Maggie Daley Park.

If you visit in mid-March, you’ll see the Chicago River dyed green for the annual St. Patrick’s Day festivities. The massive Lollapalooza music festival brings top pop and rock acts to Grant Park in late July and early August. In September, foodies head to Millennium Park for cooking demos and tastings at the Chicago Gourmet weekend.

Travel tip

Can’t decide what to eat? Choose from multiple vendors serving a global array of dishes from Italian beef sandwiches to Thai fried chicken at the indoor Time Out Market Chicago food hall. Sip cocktails in the all-season rooftop bar and try to find the hidden speakeasy.

Ready for your trip to the Windy City? Our Chicago hotel provides a comfortable base for your vacation.