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 1 of 3 — 119 listed
- All Seasons Orchard 2026 Fall SeasonAug 29 – Nov 1, 2026 — All Seasons Orchard · Woodstock, IL
- Bengtson Pumpkin Farm Fall Fest 2026Sep 4 – Nov 8, 2026 — Bengtson Pumpkin Farm · Homer Glen, IL
- Garwood Orchards Fall Daily U-Pick 2026Sep 4 – Oct 31, 2026 — Garwood Orchards · La Porte, IN
- Niles Scream Park 2026Sep 11 – Nov 7, 2026 — Niles Scream Park · Niles, MI
- The Elegant Farmer Autumn Harvest Fest 2026Sep 12 – Oct 25, 2026 — The Elegant Farmer · Mukwonago, WI
- Richardson Adventure Farm 2026 Fall Season (World's Largest Corn Maze)Sep 12 – Nov 1, 2026 — Richardson Adventure Farm · Spring Grove, IL
- Heap's Giant Pumpkin Farm 2026 Season (Minooka)Sep 13 – Oct 31, 2026 — Heap's Giant Pumpkin Farm · Minooka, IL
- Happy Times Pumpkin Fest at Didier Farms 2026Sep 16 – Oct 31, 2026 — Didier Farms · Lincolnshire, IL
- Kuipers Family Farm Fall Harvest Fest 2026Sep 18 – Nov 1, 2026 — Kuipers Family Farm · Maple Park, IL
- Harvest Tyme Fall Festival 2026Sep 19 – Oct 25, 2026 — Harvest Tyme Family Farm · Lowell, IN
- Siegel Cottonwood Farm Pumpkin Fest 2026Sep 19 – Nov 1, 2026 — Siegel Cottonwood Farm · Lockport, IL
- Duchess Manor Full Scare 2026Sep 19 – Nov 1, 2026 — Duchess Manor at The Arboretum of South Barrington · South Barrington, IL
- Duchess Manor Lights On 2026Sep 19 – Nov 1, 2026 — Duchess Manor at The Arboretum of South Barrington · South Barrington, IL
- Fermilab Public Tours — Fall 2026Sep 21 – Nov 16, 2026 — Wilson Hall, Fermi National Accelerator Laboratory · Batavia, IL
- HellsGate Haunted House 2026Sep 24 – Nov 1, 2026 — HellsGate Haunted House · Lockport, IL
- Abandoned Haunted House Complex 2026Sep 25 – Nov 7, 2026 — Abandoned Haunted House Complex · Mount Pleasant, WI
- Fall Fest at Lincoln Park Zoo — Main Program Dates 2026Sep 25 – Nov 1, 2026 — Lincoln Park Zoo · Chicago, IL
- Horror Film Series 2026 at the Egyptian TheatreSep 29 – Oct 29, 2026 — Egyptian Theatre · DeKalb, IL
- Haunted History Tours at Lincoln Park Zoo 2026Sep 29 – Oct 28, 2026 — The Patio at Café Brauer, Lincoln Park Zoo · Chicago, IL
- Cosley Zoo Pumpkin Fest 2026Oct 1–31, 2026 — Cosley Zoo · Wheaton, IL
- Desolate Acres 2026Oct 2–31, 2026 — Waukesha County Expo Center · Waukesha, WI
- Shockwave Haunts 2026Oct 2–31, 2026 — Shockwave Haunts · Whitewater, WI
- Brookfield Toy Vault First Weekend Show – new October and December 2026 datesOct 3 – Dec 6, 2026 — Brookfield Square Mall · Brookfield, WI
- Realm of Terror Haunted House 2026Oct 3–31, 2026 — Realm of Terror Haunted House · Round Lake Beach, IL
- Great Midwest Train Show — remaining 2026 datesOct 4 – Dec 6, 2026 — DuPage County Fairgrounds · Wheaton, IL
- Night of 1,000 Jack-o'-Lanterns 2026Oct 7–25, 2026 — Chicago Botanic Garden · Glencoe, IL
- Creepy Cosmos at the Manfred Olson Planetarium 2026Oct 9–30, 2026 — Manfred Olson Planetarium, University of Wisconsin-Milwaukee · Milwaukee, WI
- Illinois Railway Museum Pumpkin Train 2026Oct 10–25, 2026 — Illinois Railway Museum · Union, IL
- Haunted Hills Daytime Fall Festival 2026Oct 10–24, 2026 — Haunted Hills Farm · Merrillville, IN
- Waukesha Pokémon/TCG Non-Sports Card Show – remaining 2026 Arena datesOct 10 – Nov 21, 2026 — Waukesha Expo Center – Arena · Waukesha, WI
- Fermilab Colloquium Series — Fall 2026Oct 14 – Dec 9, 2026 — One West, Wilson Hall, Fermi National Accelerator Laboratory · Batavia, IL
- Waukesha Card Show – remaining 2026 and announced 2027 datesOct 17, 2026 – May 22, 2027 — Waukesha Expo Center – Forum · Waukesha, WI
- Wisconsin Sports Collectors Association – remaining 2026 showsOct 18 – Dec 13, 2026 — Roma Lodge · Racine, WI
- Milwaukee Lionel Railroad Club Toy Train Sale – 2026–2027Oct 18, 2026 – Mar 21, 2027 — New Berlin Entertainment Center · New Berlin, WI
- Rooftop Stargazing at UW-Milwaukee 2026Oct 20 – Dec 10, 2026 — UW-Milwaukee Physics Building rooftop · Milwaukee, WI
- Spooktacular Express After Dark 2026Oct 22, 2026 — National New York Central Railroad Museum · Elkhart, IN
- Upside Down Halloween Parade 2026Oct 31, 2026 — Russell Drive, Washington Park · Chicago, IL
- Haunted Halsted Halloween Fest and Parade 2026Oct 31, 2026 — Halsted Street between Aldine and Addison · Chicago, IL
- Brookfield Toy Vault Pokeween Trick-or-Treat Show 2026Oct 31, 2026 — Brookfield Square Mall · Brookfield, WI
- Smashing Pumpkins at Discovery Center Museum 2026Nov 1, 2026 — Discovery Center Museum · Rockford, IL