Chicago's Can't-Miss Weekend: Music, Architecture, and Hidden Gems

Chicago is overflowing with things to do, from world-renowned attractions to quirky local gems, making it an unforgettable destination for listeners visiting this week or exploring for the first time. This Saturday, feel the pulse of the city with The Lumineers’ Automatic World Tour rolling into Soldier Field at 6:30 p.m., featuring special guests St. Vincent and Lake Street Dive – doors open at 4:30 p.m. for an outdoor concert experience amid the legendary stadium’s energy.

For those who crave the best of Chicago’s iconic architecture, hop aboard a 90-minute Chicago Architecture River Tour—highly recommended for bringing the city’s skyline and history alive. Listeners who prefer a faster thrill can enjoy the Seadog Architecture Tour on the Chicago River, a 45-minute ride offering exhilarating views and a splash of excitement. Saturday nights at Navy Pier dazzle with a Fireworks Cruise aboard the Tall Ship Windy, letting you sail beneath fireworks and city lights from 9 to 10:30 p.m.

Art and movie buffs can walk in Ferris Bueller’s footsteps on a 90-minute guided tour at the Art Institute of Chicago this Saturday at 11:30 a.m., where you’ll visit the very galleries immortalized in the classic film and get fresh insights from an expert guide. Outdoors, Millennium Park is hosting large-scale art installations by Franz West, pairing monumental work with the city’s own architectural marvels.

For sports fans, the city’s vibrant scene includes Northwestern football’s kickoff this week and plenty of neighborhood league action at parks across the city. Montrose Beach is hosting the Players Beach Series outdoor volleyball event on August 30, where listeners can either compete or spectate while soaking up lake breezes and skyline views.

If you crave more hidden gems and local favorites, the Homewood Farmers Market is in full swing every Saturday through October, brimming with local flavors and handmade treasures. South of the city, the 57th Annual Frankfort Fall Festival is a highlight for Labor Day weekend, spanning August 30 to September 1—expect crafts, music, food vendors, and a festive small-town vibe.

Food lovers will want to eat their way through the Chicago Riverwalk, grabbing bites from celebrated spots like Beat Kitchen or stopping for craft beer at Chicago Brewhouse, all while enjoying street musicians and riverside scenery. For an old-school treat, the Original Rainbow Cone in Beverly has been serving its signature, multi-layered ice cream cones since 1926—a beloved Chicago dessert you can't find anywhere else.

Jazz up your evenings at the Green Mill Cocktail Lounge, a prohibition-era haunt in Uptown that still hosts world-class live jazz nightly. Meanwhile, architecture fans looking for something unique should check out The World Within: Chicago’s Best Architecture Interiors Tour, departing Saturday from the Chicago Loop, which lets you step inside some of the city's most distinctive buildings.

Whether it’s hopping on a Big Bus hop-on, hop-off tour for a breezy city overview, picnicking on the lawns of Grant Park, or discovering street art in Pilsen, Chicago is packed with activities that are fun, artistic, and sometimes a little off the beaten path. The city never gets old—there’s a reason both locals and visitors return again and again.

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