Listeners headed to Chicago this week are in for a vibrant mix of classic landmarks, live music, sports thrills, eye-catching art, and hidden gems that make the city a true summer playground. Today, catch the Chicago White Sox facing the San Francisco Giants at Guaranteed Rate Field, game time 1:10 pm, a quintessential Windy City sports experience. At the same time, the city’s beloved outdoor pools are now open, so those looking to cool off can take a dip at one of Chicago Park District’s dozens of pools, a local favorite during warm weather.
Millennium Park continues to buzz with activity. Art lovers shouldn’t miss Franz West’s monumental installations, Stonehenge and Dorit, on display in the park for an unusual mix of contemporary sculpture and skyline views. Just steps away, Sunday brings the much-anticipated “Blondell Cummings: Dance as Moving Pictures” exhibition at the Art Institute, highlighting pivotal video works by one of America’s foremost African American choreographers.
For those wanting to experience Chicago’s iconic architecture from a new angle, hop on a 90-minute Architecture River Tour departing today at 5 pm from the Summer of George dock on South Wells Street. Guides blend history, skyscraper stories, and humor for a journey along the city’s soaring riverfront. Alternatively, the Big Bus Tours’ Hop-On, Hop-Off routes let listeners explore downtown landmarks at their own pace, perfect for first-timers or those wanting a conveniently curated day.
Sunday mornings bring the bustling Wolff’s Flea Market at Allstate Arena in Rosemont, running from 6 am to 2 pm through October, where rare finds, local eats, and a lively crowd create a classic urban bazaar atmosphere. Later, cap off the night with Navy Pier’s free, award-winning fireworks show at 10 pm, regularly voted one of the nation’s best places to see fireworks. The display lights up Lake Michigan every Wednesday and Saturday all summer long, creating a magical lakeside experience.
Music fans are in luck—Millennium Park’s Summer Music Series continues each Thursday through August 7, offering free live concerts in truly stunning surroundings. The Millennium Park Summer Film Series brings free outdoor movies every Tuesday night through August 19 for a classic movie-and-picnic experience. Listeners seeking jazz can visit Harper Court’s free al fresco performances, spotlighting top local talent in Hyde Park, and Shedd Aquarium’s Jazzin’ at the Shedd series every Wednesday night pairs aquatic ambiance with live bands.
Chicago’s food scene is on full display with guided walking tours in Chinatown and bikes, bites, and brews adventures across different neighborhoods, as noted by My Guide Chicago. The South Loop Farmers Market delivers a twice-weekly spread of farm-fresh produce and treats, while the historic Maxwell Street Market, held every second Sunday through October, is a unique opportunity to sample global street eats, see local music, and shop for vintage treasures.
Sports enthusiasts can check out the Chicago Hounds professional rugby matches at SeatGeek Stadium, or take in a free Chicago Fire FC II soccer game—a great family-friendly choice. Looking further into summer, Bulls Fest at the United Center in August turns the city into a basketball celebration with tournaments, food, art, and appearances by Bulls legends, all free to attend.
Hidden gems include T.I.P. Fest, the city’s largest platform for young artists, with auditions and showcases that spotlight Chicago’s up-and-coming creative talent. For a blend of entertainment and spectacle, Teatro Zinzanni’s “Love, Chaos & Dinner” under the big tent downtown delivers a unique mashup of cabaret, circus, and gourmet dining, running today and most evenings through summer.
Finally, for those wanting to blend music and nature, the Ravinia Festival in nearby Highland Park features over 100 concerts across genres this season, with legends like Janelle Monáe, The Roots, and the Chicago Symphony Orchestra. Foodies and music lovers alike gather with picnics on the lawn or reserved pavilion seats for a uniquely local summer tradition.
With outdoor adventures on the Lakefront Trail, yoga and fitness classes in Millennium Park, beachside dining at Pier 31, and so many cultural happenings, Chicago in late June delivers unforgettable experiences for tourists and locals alike, blending iconic attractions and under-the-radar highlights that define #SummerTimeChi.
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