Arts in the Dark Halloween Parade
Over 100,000 spectators gather along Columbus Drive as illuminated floats, giant spectacle puppets, and mariachi and circus troupes parade beneath the city skyline.
Updated dailyThis weekend in Chicago: Fri, Oct 23 – Sun, Oct 25, 2026
Find current events, restaurants, family activities, and quick getaway ideas in Chicago, IL. WonderKit curates these picks daily so the page stays useful for both local search and trip planning.
11 hand-picked things to do in Chicago, IL right now · 3 with confirmed dates
Photo: Ozzie Stern / Unsplash
A sample plan built from this week's Chicago, IL picks — the same day-by-day itinerary WonderKit drafts for your group in about a minute.
A focused retrospective in Washington Park tracing how African American writers, sculptors, and painters forged creative liberation and international fellowship in 20th-century Paris.
Chef Jimmy Papadopoulos brings coal-fired cooking to this British-influenced tavern, serving smoked ember oysters, bone-in swordfish, and hand-pulled cask ales beside a crackling hearth.
An interactive, after-hours escape room puzzle game played throughout the Griffin MSI exhibits, centered on decoding clues to reboot a secret clean power grid.
A massive two-acre corn maze, thousands of illuminated pumpkins, axe-throwing lanes, and seasonal cider trucks pop up in the center of industrial Goose Island for the fall run.
Chefs Zubair Mohajir and Jacob Dela weave Indian and Filipino culinary heritages together over charcoal grills—think spiced goat biryani, garlic vinegar-drizzled duck, and South Indian red rice.
Derek Trucks and Susan Tedeschi bring their searing 12-piece American blues, rock, and soul ensemble to the historic Chicago Theatre stage.
Over 100,000 spectators gather along Columbus Drive as illuminated floats, giant spectacle puppets, and mariachi and circus troupes parade beneath the city skyline.
A brisk autumn night calls for this snug 30-year-old French bistro: steamy pots of French onion soup, roasted duck leg with spätzle, and a carafe of red wine packed along red checkered tablecloths.
Hike through 18 sandstone gorges blanketed in gold and russet foliage, warm up with apple cider donuts in historic Utica, and finish with a hearty supper in the 1930s Great Hall lodge.
Ready-made, day-by-day itineraries built from real local spots — grab one and make it yours.
Fall parades, after-hours museum games, and live blues-rock
Over 100,000 spectators gather along Columbus Drive as illuminated floats, giant spectacle puppets, and mariachi and circus troupes parade beneath the city skyline.
An interactive, after-hours escape room puzzle game played throughout the Griffin MSI exhibits, centered on decoding clues to reboot a secret clean power grid.
Derek Trucks and Susan Tedeschi bring their searing 12-piece American blues, rock, and soul ensemble to the historic Chicago Theatre stage.
Tell us who's going and WonderKit drafts three Chicago, IL trip ideas in about a minute — free, and you see them before creating an account.
Warm hearths, fresh masa, and cozy dining for crisp October days
Chef Jimmy Papadopoulos brings coal-fired cooking to this British-influenced tavern, serving smoked ember oysters, bone-in swordfish, and hand-pulled cask ales beside a crackling hearth.
Chefs Zubair Mohajir and Jacob Dela weave Indian and Filipino culinary heritages together over charcoal grills—think spiced goat biryani, garlic vinegar-drizzled duck, and South Indian red rice.
A brisk autumn night calls for this snug 30-year-old French bistro: steamy pots of French onion soup, roasted duck leg with spätzle, and a carafe of red wine packed along red checkered tablecloths.
Fresh exhibits, seasonal pop-ups, and limited installations
A massive two-acre corn maze, thousands of illuminated pumpkins, axe-throwing lanes, and seasonal cider trucks pop up in the center of industrial Goose Island for the fall run.
A focused retrospective in Washington Park tracing how African American writers, sculptors, and painters forged creative liberation and international fellowship in 20th-century Paris.
Autumn road trips within two hours of the Loop
Hike through 18 sandstone gorges blanketed in gold and russet foliage, warm up with apple cider donuts in historic Utica, and finish with a hearty supper in the 1930s Great Hall lodge.
Climb towering lakefront sand dunes without the summer crowds, pick heirloom Northern Spy apples at Crane's Orchard, and spend the afternoon sipping hard cider along Michigan's Red Arrow Highway.
Walk the historic 21-mile shoreline path past Gilded Age summer mansions surrounded by peak oak and maple color, followed by warm chowder and lake views at Popeye's on Geneva Lake.
Current local highlights in Chicago, IL include Arts in the Dark Halloween Parade, Escape the Museum: The Infinite Grid, and Tedeschi Trucks Band: Future Soul Tour. WonderKit refreshes this guide daily so the picks reflect real local happenings.
The sections above show this week's events, weekend plans, and new-and-notable openings in Chicago, IL, updated daily.
The "Eat & Drink" section above lists restaurants and food spots locals are recommending in Chicago, IL right now.
Tell us who's going and WonderKit drafts three Chicago, IL trip ideas in about a minute — free, and you see them before creating an account.





