This week in Chicago, the city sparkles with unique experiences for adventurous tourists and curious locals alike. Dive into Chicago’s energetic sports scene by catching international soccer at Soldier Field with the Premier League Summer Series. Or, for classic American fun, root for the Chicago White Sox as they take on the Philadelphia Phillies at Guaranteed Rate Field—the series wraps up July 30. If you love the water, escape the bustle by hopping aboard the Chicago Skyline Sail, available daily through September 28. Glide along Lake Michigan’s waves while you soak in epic city views from Tall Ship Windy at Navy Pier.
If exploring on foot is more your pace, take a Lamborghini Chicago City Cruise Tour through the heart of downtown, or experience the city’s world-renowned architecture with a guided trip along the Chicago River. Chicago Architecture Center’s tours spotlight icons like Willis Tower, Tribune Tower, the Wrigley Building, and the bustling Loop packed with cultural gems. Millennium Park’s famous Cloud Gate (“The Bean”) and the Art Institute of Chicago with its impressive global collections are always crowd-pleasers.
Chicago is a music lover’s paradise, especially in the summertime. Grant Park Music Festival offers free classical concerts on Millennium Park’s Great Lawn all season long. Don’t miss the wild rhythms and public dance lessons at Chicago SummerDance, where listeners can sample everything from salsa to swing across city parks. The Tuesdays on the Terrace jazz series at the Museum of Contemporary Art charms with open-air sounds and stellar city views—this free series runs through August.
If street festivals and outdoor adventure call your name, the city delivers. The Chicago Air and Water Show sweeps into Lake Michigan August 15-17, dazzling with roaring jets and aquatic stunts in one of the nation’s largest and free spectacles. For more active fun, join Bike the Drive on August 31; this annual event transforms Lake Shore Drive into a car-free route for thousands of cyclists, ending with a festive gathering in Grant Park. Water lovers can also join the Paddle and Plant initiative from Friends of the Chicago River and Shedd Aquarium: volunteers get hands-on restoring habitats by canoeing and planting along the Chicago-Calumet river system.
Art and theater thrive outdoors in the warmer months. Watch Chicago Shakespeare Theatre’s “A Midsummer Night’s Dream” in city parks through August 17 or laugh along with kids at performances like “Book Up!” and “Ice Cream Circus!” at multiple neighborhood parks until mid-August.
Delight your taste buds with a deep dive into Chicago’s food scene. The Taste of Chinatown Food Walking Tour is a favorite for sampling dim sum, noodles, and sweet treats in one of the city’s most vibrant neighborhoods. For rooftop cocktails, perch atop the Navy Pier’s Offshore Rooftop lounge for sweeping lake views—especially magical during the Navy Pier fireworks every Wednesday and Saturday night through Labor Day.
For outdoor serenity, Wooded Island in Jackson Park offers peaceful birdwatching every Saturday, while the Humboldt Park Arboreal Society spins live DJ sets in the lush greenery on select Sundays in August. If you’re interested in the city’s hidden stories, book the Mob and Crime Bus Tour for tales of infamous gangsters and legendary crimes.
And don’t overlook surprise local gems. From wild yoga on Goose Island’s Wild Mile with scenic river views to the fabulous fountains featured in guided bike tours, Chicago’s neighborhoods pulse with creativity. The city’s summer continues to buzz with overlapping festivals, pop-up markets, and spontaneous music sessions, making every night out a potential new favorite memory.
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