80 Things to Do in Chicago 2026 — Events, Shows & Activities

Save 5.00%! Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury... Chicago from C$334.07

Save 5.00%! Arrival Private Transfer: O'Hare Airport ORD to Chicago in Luxury Ca... Chicago from C$334.07

Save 5.00%! Departure Transfer: Chicago to O'Hare Airport ORD by Luxury SUV Chicago from C$288.8

Save 5.00%! Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Luxury SU... Chicago from C$288.8

Save 5.00%! Airport Transfer: O'Hare Airport ORD to Chicago by Luxury SUV Chicago from C$288.8

Save 6.00%! Arrival Transfer: O'Hare Airport ORD to Chicago by Luxury SUV Chicago from C$230.15

Save 6.00%! Departure Private Transfer: Chicago to O'Hare Airport ORD in Busines... Chicago from C$214.7

Save 6.00%! Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business... Chicago from C$214.7

Save 6.00%! Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Business... Chicago from C$214.7

Save 20.00%! Downtown Chicago City Tour in a Super Car [30 Minute Experience] Chicago from C$182.38

Save 7.01%! Chicago Insider Segway Tour Chicago from C$95.41

Save 8.01%! 2-Hour Chicago Lakefront & Museum Campus Segway Tour Chicago from C$91.76

Save 14.99%! Chicago Sunset Segway Tour Chicago from C$90.83

Save 10.00%! Lakefront Segway Tour in Chicago Chicago from C$89.76

Save 20.00%! Mexican Tacos Cooking Class With Local Chef in Chicago Chicago from C$85.49

Save 10.00%! Chicago Amazing Lakefront Bike Tour Chicago from C$62.83

Save 13.00%! Chicago Haunts and Hooligans Tour Chicago from C$49.54

4* Radisson Blu Manchester Airport Health Club Day: 2 Treatments, Health Club Ac... Chicago from £49

Save 20.00%! Journey of the Chicago Flag Bus Tour Chicago from C$47.87

Save 25.01%! Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour Chicago from C$47.02

Save 20.01%! Chicago Hauntings Original Ghost Walk through Old Chicago Chicago from C$45.59

Save 20.04%! Chicago Scavenger Hunt Adventure Chicago from C$33.06

Latina Por Siempre Foundation Room at House of Blues Chicago Sun, 16 Aug 2026

Vino Louden Blues Band/Nora Jean Wallace Blues Band Kingston Mines - Chicago Blues Center Sun, 16 Aug 2026 from $23

The Notebook (Chicago) James M. Nederlander Theatre Sun, 16 Aug 2026

The Outsiders (Chicago) Cadillac Palace Sun, 16 Aug 2026

Diggy Graves – The No Vacancy Tour Bottom Lounge Sun, 16 Aug 2026

MAMAMOO 2026 US TOUR Wintrust Arena Sun, 16 Aug 2026

She Outside: #ChiTownEdition The Chicago Theatre Sun, 16 Aug 2026

Isaiah Sharkey Garcia's Chicago Sun, 16 Aug 2026

Club 1BD Chicago ft. DJ David & Hunny Bee Thalia Hall Sun, 16 Aug 2026 from $39.96

Eddie and the Getaway with Gavin Hughes Joe's on Weed Street Sun, 16 Aug 2026 from $25.79

Rachel is Kozi w/ JFK Healthworld and Modern Daybreak, Constant Headache Cubby Bear Sun, 16 Aug 2026 from $13.88

Eslabon Armado - Amor Nocturno Aragon Ballroom Sun, 16 Aug 2026

Darksoft , Ghost Days, Nothing But Silence Reggies Music Joint Sun, 16 Aug 2026

Pretty Crooked, Shwarma, Psythã˜N, Velvet Snakes Reggies Bananna's Shack Sun, 16 Aug 2026

The Outsiders - Chicago Cadillac Palace Theatre Sun, 16 Aug 2026

Pizza City Fest - Chicago 430 on Rush Sun, 16 Aug 2026

The Notebook - The Musical - Chicago James M. Nederlander Theatre Sun, 16 Aug 2026

St. Louis Cardinals at Chicago Cubs Wrigley Field Sun, 16 Aug 2026

Chasewest Radius Chicago Sun, 16 Aug 2026

Drunk Romeo & Juliet - Chicago The Lion Theatre Sun, 16 Aug 2026

Portland Timbers at Chicago Fire FC Soldier Field Sun, 16 Aug 2026

Chiodos with 156/Silence House of Blues Chicago Sun, 16 Aug 2026

Flight of Beer at the Pilot Project Tasting Room 2140 N Milwaukee Ave Mon, 17 Aug 2026 from $16

Hidden In Plain Sight: Chicago Prohibition Tour 226 South Wabash Avenue, Chicago Mon, 17 Aug 2026 from $45

The Art Institute of Chicago: Skip-The-Line & Semi-Private Tour 111 South Michigan Avenue, Chicago Mon, 17 Aug 2026 from $90.1

Underground Donut Tour - Chicago's First Donut Tour 401 N Franklin St Mon, 17 Aug 2026 from $69.95

Private 45-Minute Chicago Skyline Helicopter Tour 905 West Irving Park Road, Schaumburg Mon, 17 Aug 2026 from $283

K-Love Live with CeCe Winans, Jeremy Camp and Andrew Ripp The Chicago Theatre Mon, 17 Aug 2026

Christian Johnson City Winery - Chicago Mon, 17 Aug 2026

The Second City - 113th Mainstage Revue The Second City Mainstage Theatre Mon, 17 Aug 2026

millkzy Avondale Music Hall Mon, 17 Aug 2026

St. Lucia Park West Mon, 17 Aug 2026

Siddhartha The Auditorium Theatre - Chicago Mon, 17 Aug 2026

Chiodos with 156/Silence House of Blues Chicago Mon, 17 Aug 2026

All Ohio Balloon Festival The Fields Studios Mon, 17 Aug 2026

The Field Museum of Natural History: Early Access + Guided Tour + Exhibitions 1400 South Lake Shore Drive, Chicago Tue, 18 Aug 2026 from $73

Premier Dinner Cruise on the Chicago River Chicago Tue, 18 Aug 2026 from $164.01

Tiffany in Chicago: Guided Tour 78 E Washington St, Chicago, IL , USA Tue, 18 Aug 2026 from $30

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