City guide
Things to do in Chicago this weekend
Everything below is within about a two-hour drive of Chicago, IL — festivals, fairs, markets, museum days and one-off weekends, refreshed as new dates are confirmed. Want a wider net? The main explorer stretches the radius to four hours and lets you filter by cost and category.
This weekend near Chicago
13 listed
- Zoo Boo 2026 — Potawatomi ZooOct 16–25, 2026 — Potawatomi Zoo · South Bend, IN
- Boo at the Zoo 2026 (Milwaukee County Zoo)Oct 16–24, 2026 — Milwaukee County Zoo · Milwaukee, WI
- Sycamore Pumpkin Festival 2026Oct 21–25, 2026 — Downtown Sycamore / courthouse lawn · Sycamore, IL
- Milwaukee Astronomical Society Open House: Spooky Skies 2026Oct 23, 2026 — Milwaukee Astronomical Society Observatory · New Berlin, WI
- Arts in the Dark Halloween Parade 2026Oct 24, 2026 — Columbus Drive, north from Balbo to Jackson · Chicago, IL
- All Aboard the Spooktacular Express 2026Oct 24, 2026 — National New York Central Railroad Museum · Elkhart, IN
- Music Box of Horrors 2026Oct 24–25, 2026 — Music Box Theatre · Chicago, IL
- South Bend Fall Artisan Market 2026Oct 24–25, 2026 — Century Center · South Bend, IN
- Pontiac Family Fall Fest 2026Oct 24, 2026 — Chautauqua Park · Pontiac, IL
- Family Spooktacular 2026Oct 24–25, 2026 — Naper Settlement · Naperville, IL
- Chicago Women's Expo + Great Food Expo 2026Oct 24–25, 2026 — Donald E. Stephens Convention Center — Hall F · Rosemont, IL
- Brookfield Toy Vault October Funko Show 2026Oct 24, 2026 — Brookfield Square Mall · Brookfield, WI
- Chicago Toy Show — October 2026Oct 25, 2026 — Kane County Fairgrounds · St. Charles, IL
Coming up near Chicago
Page 2 of 3 — 119 listed
- Bots & Bolts at Discovery World 2026Nov 1, 2026 — Discovery World · Milwaukee, WI
- Northern Lights at the Manfred Olson Planetarium 2026Nov 6 – Dec 11, 2026 — Manfred Olson Planetarium, University of Wisconsin-Milwaukee · Milwaukee, WI
- Rock-Con 2026Nov 6–8, 2026 — Tebala Event Center · Rockford, IL
- Holiday Market at Wilder Mansion 2026Nov 6–7, 2026 — Wilder Mansion · Elmhurst, IL
- Brookfield Toy Vault Pokémon Card & Collectible Show — November 2026Nov 7–8, 2026 — Brookfield Square Mall · Brookfield, WI
- Chicago Toy & Game Fair 2026Nov 7–8, 2026 — Donald E. Stephens Convention Center · Rosemont, IL
- Trainfest 2026Nov 7–8, 2026 — Baird Center · Milwaukee, WI
- The Twisted Dreams Horror Show 2026Nov 7, 2026 — The Avalon Atmospheric Theater · Milwaukee, WI
- Rockford Arts & Crafts Holiday Spectacular 2026Nov 7–8, 2026 — Mercyhealth Indoor Sports Center · Rockford, IL
- Get Lit: Weird Science 2026Nov 10, 2026 — American Writers Museum · Chicago, IL
- Chicago Fall Showcase of Miniatures 2026Nov 13–14, 2026 — Wyndham Garden Hotel · Schaumburg, IL
- Illuminated Walk Through Country Christmas 2026Nov 13–25, 2026 — The Ingleside Hotel · Pewaukee, WI
- Frostmoon Faire 2026Nov 14, 2026 — The Dole · Crystal Lake, IL
- Stars and Stories at the Manfred Olson Planetarium 2026Nov 14, 2026 — Manfred Olson Planetarium, University of Wisconsin-Milwaukee · Milwaukee, WI
- K-Town Holiday Toy & Collectible Show 2026Nov 15, 2026 — Fountain Banquet Hall · Sturtevant, WI
- Christkindlmarket Chicago 2026Nov 20 – Dec 24, 2026 — Daley Plaza · Chicago, IL
- Christkindlmarket Aurora 2026Nov 20 – Dec 24, 2026 — RiverEdge Park · Aurora, IL
- Christkindlmarket Wrigleyville 2026Nov 20 – Dec 31, 2026 — Gallagher Way · Chicago, IL
- Chicago Sports Spectacular — November 2026Nov 20–22, 2026 — Donald E. Stephens Convention Center · Rosemont, IL
- ZooLights 2026-2027 — Lincoln Park ZooNov 20, 2026 – Jan 3, 2027 — Lincoln Park Zoo · Chicago, IL
- Days of the Dead Chicago Winter 2026Nov 20–22, 2026 — Marriott Chicago O'Hare · Chicago, IL
- Christmas on the Fox 2026Nov 21–22, 2026 — Prairie Events Center, Kane County Fairgrounds · St. Charles, IL
- Muscle Car and Corvette Nationals 2026Nov 21–22, 2026 — Donald E. Stephens Convention Center · Rosemont, IL
- Holiday Magic 2026-2027 — Brookfield Zoo ChicagoNov 21, 2026 – Jan 3, 2027 — Brookfield Zoo Chicago · Brookfield, IL
- Wintrust Magnificent Mile Lights Festival 2026Nov 21, 2026 — North Michigan Avenue and Lights Festival Lane · Chicago, IL
- Fulton County Historical Power Association Toy Show 2026Nov 22, 2026 — Fulton County Museum · Rochester, IN
- Chicago Thanksgiving Parade 2026Nov 26, 2026 — State Street parade route · Chicago, IL
- Chicago TARDIS 2026Nov 27–29, 2026 — The Westin Chicago Lombard · Lombard, IL
- Country Christmas 2026-2027 — Drive-ThroughNov 27, 2026 – Jan 2, 2027 — The Ingleside Hotel · Pewaukee, WI
- Valparaiso Winter Fest & Tree Lighting 2026Nov 28, 2026 — Central Park Plaza · Valparaiso, IN
- Milwaukee Lionel Railroad Club Open House – Fall 2026Nov 28–29, 2026 — Milwaukee Lionel Railroad Club – Parkland Plaza · New Berlin, WI
- Brookfield Toy Vault Black Friday Weekend Show 2026Nov 28–29, 2026 — Brookfield Square Mall · Brookfield, WI
- One of a Kind Holiday Show Chicago 2026Dec 3–6, 2026 — THE MART · Chicago, IL
- Midwest FurFest 2026Dec 3–6, 2026 — Donald E. Stephens Convention Center · Rosemont, IL
- Krampus Bazaar — World Oddities Expo Chicago 2026Dec 5–6, 2026 — Donald E. Stephens Convention Center — Hall G · Rosemont, IL
- West Allis Christmas Parade 2026Dec 5, 2026 — Downtown parade route along Greenfield Avenue · West Allis, WI
- Nappanee Christmas Parade 2026Dec 5, 2026 — Downtown Nappanee parade route · Nappanee, IN
- The Naughty List 2026Dec 5, 2026 — Best Place at the Historic Pabst Brewery · Milwaukee, WI
- Christmas at Macktown 2026Dec 6, 2026 — Macktown Living History · Rockton, IL
- Milwaukee Krampusnacht 2026Dec 6, 2026 — Best Place at the Historic Pabst Brewery and the Historic Brewery District · Milwaukee, WI