This weekend’s headliner is Halloween! We’ve included them here, but we’ve also got the Best Fun & Festive Events in Chicago that we’re updating regularly! There are trivia nights, puppy costume contests & parades, spooky stories and so much more! Open House Chicago also continues with self-guided tours and online events throughout the month, and we’ve still got Farmer’s Markets and so much more.
Here are the highlight events for this weekend in Chicago.
Click on each event for more information and pricing and check with the venue for any changes or cancellations.
Friday, October 21st
Eerie Evening at the Bridgehouse Museum
5 pm – 9 pm
376 N Michigan Ave
Chicago, IL 60601
Saturday, October 22nd
Spooky Zoo Spectacular
10 am – 2 pm
Lincoln Park Zoo
2001 N Clark St
Chicago, IL 60614
Boo Palooza
10 am – 2 pm
1425 N. Damen
Chicago, IL 60622
Lakeview Halloween Pup Crawl 2022
10 am – 2 pm
Drew’s on Halsted
3201 North Halsted Street
Chicago, IL 60657
Spooktacular on Clark Street
Sat & Sun 1 pm – 4 pm
Clark from Armitage to Diversey
UPSIDE DOWN Halloween Parade
Noon – 3pm
Washington Park, Russell Drive
Chicago Fall Market for Makers
11 am – 5 pm
Artifact Events
4325 N Ravenswood
Chicago, IL 60613
Annual S’mores & Stories
3 pm – 5 pm
Kilbourn Park
3501 N Kilbourn Ave
Chicago, IL 60641
Trunk or Treat
3 pm – 5 pm
McFetridge Sports Center
3843 N California Ave
Chicago, IL 60618
Sunday, October 23rd
RUN for BEER Series
Spiteful Brewing
2024 W Balmoral Ave
Chicago, IL 60625
Kids Halloween Party
4 pm
Park and Field
3509 W Fullerton Ave
Chicago, IL 60647
Monday, October 24th
Trick or Treat on Southport
4 pm – 8 pm
Southport Ave from Roscoe to Grace
Wednesday, October 26th
Halloween Trivia
7 pm
The Den Bar & Lounge
1329 N Milwaukee Ave
Chicago, IL 60622
If you didn’t get your Halloween decorations up yet, there’s still time! There are some many fun events this weekend, so get out there and enjoy the city events this October 20-26 weekend.
If you would like to have an event featured, email Maureen at hello@yourlincolnparklife.com
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