31 of the Best Things to Do in Chicago this October

October (like every season since March) is looking a bit weird this year. But the spooky season does not have to be canceled. You can still get up, get out and get festive this fall with these fun October events happening around Chicago! 

Don’t forget to tag us in your posts on Instagram @betterchicago

Sept. 25 – Nov. 1: Fall At The Zoo

Brookfield Zoo

For safety reasons Brookfield Zoo has redesigned their well known Boo At The Zoo and instead are introducing Fall at the Zoo, offering so many fun reasons to pay a visit this October, such as their Fall Selfie Sweepstakes. Every week they will be giving out prizes to guests who capture a cute, quick pic at one of their multiple selfie stations set up throughout the zoo.
8400 31st St, Brookfield, IL

Oct. 1 – 8: Recycled Art Sale Benefit

Alexis Miller

Highland Park will be holding their annual Recycled Art Sale Benefit in a socially distanced setting. Come see the array of previously owned paintings, jewelry, frames, sculptures, etc. and make another man’s trash your eco-friendly treasure.
1957 Sheridan Rd, Highland Park, IL

Oct. 1 31: The Music Box is hosting a drive-in horror movie marathon in Pilsen

Endless hours of horror?! That’s right. Put your brave face on and head to the Chi-Town Movies Drive-In through October 31 for a month of fearful, frightful films. Each weekend is themed, Grindhouse Fridays, Rip-Off Saturdays, and Sequel Sundays, for your preference. 
3733 N Southport Ave, Chicago IL / 2343 S. Throop St, Chicago IL

Oct. 1 31: UNICEF Trick-or-Treat Fundraiser

Starting Oct. 1, teachers and parents are encouraged to register children and create profiles online where they will receive a Virtual Collection Box and customized QR code. Children can earn trick-or-treat coins that add up to real-life earning. As they collect the coins, they will be able to choose where they want them to gogiving them the power to impact children around the world.

Oct. 1 31: Crypt Run

Best buddies for Best Buddies. You and your friends can show your support for the Illinois Best Buddies program by participating (safely) in a virtual 5k/10k run or walk. Once registered, you have until the end of October to complete the route provided or your own. The catch? You have to do it in your Halloween costume. Virtual event.

Oct. 1 Nov. 1: Scarecrow Trail

The students and scouts of Chicago’s Morton Arboretum have put in a ton of hard work and creativity to create an autumn experience you won’t forget. Visit the Morton Arboretum to get a look at the collection of scarecrows they designed. At the end of the very impressive display you will be able to score your favorite scarecrow.
4100 IL-53, Lisle, IL

Oct. 2 31: Drive-Thru Haunted House

Replay in Lincoln Park is introducing a new spin on the classic haunted forest experience. This year they are hosting a drive-thru haunted house in their alley. This experience is expected to leave guests terrorized and frozen in fear. With life like props, tons of fake blood, and a scary movie to set the tone, you won’t want to miss this. Scary season is in full effect at Replay this year.
Tickets for Alley of Darkness / Tickets for Stranger Patio
2833 N Sheffield Ave, Chicago

Oct. 2 Nov. 27: The Stoop Comedy Show

Come fall, the only fame a front stoop gets depends solely on its pumpkin game. But not in this case. The Stoop Comedy Club has arranged for comics from around the city to put on a show right from a porch in Logan Square. Don’t forget to mask up before you laugh. Chicago address TBD.
Get your tickets here.

Oct. 5: Corporate America Supporting Hispanic Stars

A certain issue at hand in the business world is the lack of representation. Join the conversation and learn about the most proactive ways to use your passion about Hispanics in corporate America. The lineup of speakers for this very powerful webinar include: Sandra Campos, Former CEO of Diane Von Furstenberg, Founder, Investor and Operating Partner of Fashion Launchpad; Mauricio Gutierrez, President and CEO of NRG; Maria Rios, CEO of Nation Waste; Damian Rivera, CEO of ALPFA; and Moderator, Claudia Romo Edelman, Founder of We Are All Human. Virtual event.

Oct. 6: Design Your Own Sign Using Reclaimed Wood Virtual Workshop (Three week series)

Julie Wildman

Skilled local calligrapher, Julie Wildman, has put together an online class to design your own wooden sign. Over the course of three sessions, you will paint your sign and stain it and inscribe it after practicing the lettering with Julie. So start thinking of your phrase now, because you’ve got a sign to make! Virtual event.

Oct. 7: Activating the Internal Talent Marketplace: Unleash the Power of Your Workforce

As a business owner you have had to rearrange the foundation of how your company works as a result of Covid-19: tactics, techniques, technology, etc. Interested in knowing if these new ways are helping or hurting you? Join this webinar to learn how you can reimagine the workforce. Virtual event.

Oct. 9: Virtual Tree ID Walk

See the leaves and learn about their trees. On October 9 (peak leaf peeping time!) Garfield Park Conservatory is hosting a virtual course on how to identify certain trees around Chicago based on their subtle characteristics. Although the event is free, donations are always appreciated. Virtual event.

Oct. 9, 16, & 23: Candlelight Open Air: Celebrating 250 Years of Beethoven

Imagine sitting comfortably in your warmest attire outside in Chicago in the fall, surrounded by candles and listening to beautiful live classical music. Sounds like a scene from a movie. Experience this wildly popular experience firsthand thanks to the doing of Fever Originals Candlelight series.
311 N Morgan St., Chicago, IL

Oct. 10: Chicago Hauntings Original Ghost Walk Through Chicago

Chicago Hauntings

Chicago is full of haunted history. What better time of the year to walk through Old Chicago and experience its history and beloved hauntings.
325 N LaSalle Dr, Chicago IL

Oct. 10: Embroidery Basics Workshop

What’s a better time than now to start a new hobby? Join One River School in Evanston for an afternoon embroidery basics workshop! You will learn the basic stitches and create a design of your own.
1033-1035 Davis St., Evanston, IL

Oct. 13: The Office Trivia

Think you’re the #1 fan of The Office? Let’s put you to the test. Pinstripes Bowling is hosting a trivia night and the theme is…. The Office. And yes, prizes will be awarded to those who win.
435 East Illinois St, Chicago, IL

Oct. 14: Haunted Dining In The Dark

Calling all dining daredevils! Dining in the dark is an utmost unique experience brought to you by the Hubbard Inn. Here’s how it works. You will be served a three course SECRET meal in complete DARKNESS. Oh and one more thing… you’ll be eating in HAUNTED surroundings.
110 W Hubbard St, Chicago, IL

Oct. 14 18 & 21 25: Night of 1,000 Jack-o’-Lanterns Fest

Chicago Botanic Garden

Jack is back! The Chicago Botanic Gardens announced the return of their famous Night of 1,000 Jack-o’-Lanterns Fest. The pumpkins will be placed spaced farther apart and masks will be required so that you can still come and safely enjoy the incredible talent and work of these artists.
1000 Lake Cook Rd, Glencoe, IL

Oct. 16: What’s Fair? Restoring Progress at Home and at Work Amid COVID

Eve Rodsky, author of best selling book “Fair Play” is speaking on a webinar focusing on women reaching their full potential both in the home and at work, specifically during this pandemic. As many women have experienced in these past few months, working from home has also included homeschooling and taking care of household responsibilities. Rodsky is making sure women don’t get cut short on reaching their goals. Register to tune in to hear her thoughts and advice. Virtual event.

Oct. 17 18: Glencoe Art Walk

As tradition calls for, the 12th annual Glencoe Art Walk will still be taking place while taking the necessary precautions to keep guests safe. Artists will be putting their hard work on display in the forms of jewelry, sculptures, paintings and apparel. Come for the art and stay for all that Glencoe has to offer.
700 Vernon Ave, Glencoe, IL

Oct. 21: Cooking Up A Cure

Is your kitchen in a hosting mode? Because celebrity chefs and beverage connoisseurs are coming right to you during this virtual Cooking Up A Cure event! This is the 12th annual fundraising event by the Scleroderma Foundation of Greater Chicago chapter. Enjoy interviews, cooking demos, new recipes and even a silent auction all in an effort to raise money and awareness for Scleroderma patients. Virtual event.

Oct. 21: On Point: Political Experts Bring Presidential Election Analysis

The Executives’ Club of Chicago

It’s election season – VOTE! – and there is a lot to the process. Whether you just have a strong interest in politics, or if you are trying to gain as much information before filling out your ballot, this webinar would be great to attend. It’s an incredible opportunity to hear from the following intelligent individuals who know politics incredibly well: Alex Castellanos, Founder of NewReupublican.org and Co-Founder of Purple Strategies; Rahm Emanuel, Former Mayor of Chicago; and Laura Washington, Columnist for the Chicago Sun-Times, Political Analyst for ABC-7 Chicago. Virtual event.

Oct. 22: The Do’s & Don’ts of Data Utilization: Case Studies in the Food & Beverage Industry

Interested in the ways of the food and beverage industry? Register to be a part of the interactive Zoom session with Rebecca Lederhouse, Counsel of Baker McKenzie and Adam Aft, Partner of Baker McKenzie. The two will be dissecting common practices and trending techniques in the industry and which are helping and which are hurting. Virtual event.

Through Oct. 25: Pop-Up Haunted Parks

This October, each weekend a different park in Wilmette will host a haunted Halloween pop-up. Different scenes, same screams!

  • Oct 2 4 at Maple Park, 398 Maple Ave, Wilmette
  • Oct 9 11 at Vattmann Park, 1461 Lake Ave, Wilmette
  • Oct 16 18 at Thornwood Park, 2400 Thornwood Ave, Wilmette
  • Oct 23 25 at Forest Park, 1848 Forest Ave, Wilmette

Oct. 26: Clean, Smart, Reliable, Affordable: Piecing Together Our Energy Future

The Executives’ Club Of Chicago presents a webinar on clean engery. The webinar features two guests that have much knowledge on the subject, Guest Speaker: Joseph Dominguez, CEO of ComEd and Moderator: Linda Imonti, Office Managing Principal of KPMG. Virtual event.

Oct. 28: Business Technology Forum

It’s safe to say that no one business is running the same way in which it did at the start of the year 2020. Since the outbreak of the pandemic, every company has had to make changes and sacrifices to keep their businesses up and running successfully. And with that a lot of new technology and methods have been put into play. Join in on this business technology forum, hosted by The Executives’ Club of Chicago, to reflect and learn how these new ways can be beneficial to your business down the road. Virtual event.

Oct. 29: Adults Night Out: The Pumpkin Glow 

Lincoln Park Zoo

The Lincoln Park Zoo has put together an evening for adults after dark, and get this – it’s all fall themed. From the food and cocktails to a socially distanced movie, Adults Night Out: The Pumpkin Glow has been made so that all you have to decide is if you want to start at the pumpkin patch or the haunted trail. Bundle up, it’s time to GLOW!
2001 N Clark Street, Chicago, IL 60614

Oct. 31: Haunted Igloo At The Godfrey Hotel

This concept is for those who want to celebrate Halloween but their head is in a winter frame of mind. The Godfrey Hotel has just released its first-ever haunted igloo experience. Picture this: you’re safely inside those cool little heated igloos on a rooftop in Chicago with your friends, sipping on autumn themed beverages, surrounded by spooky surprises. These scary touches include frightening decor, a fire dancer, and a “best costume” prize giveaway!

Through Oct. 31: The Paulina Patch

Paulina Patch
Waterhouse Tavern

Waterhouse Tavern’s newest pop-up, The Paulina Patch, is the perfect place to stop off at for a seasonal experience. The pumpkin patch inspired setting, of hay bales and scarecrows, offers almost every fall classic drink you can think of. From spiked apple ciders and autumn-spiced sangria to Oktoberfest beers and a Tito’s pumpkin-spiced latte, the menu screams fall. 3407 N Paulina St, Chicago, IL

Through Oct. 31: Brews n ‘Baahhs’

Some do yoga with goats and others drink beer with them! The Glenn Art Farm and One Lake Brewing have teamed up for Brews n ‘Baahhs’. You will get a private experience to hang out with some goats followed by flights of delicious home made craft beer on a rooftop!
451 N Waller Ave, 60644

Through Oct. 31: The Pumpkin Eating Dinosaur

Have you ever seen a pumpkin eating dinosaur? Well, it’s 2020 and almost anything is possible. Head over to Goebbert’s Pumpkin Patch & Apple Orchard to see it for yourself. While you’re there, go apple and pumpkin picking, check out the new carousel, go through the straw maze, and even get a camel ride. There are tons of activities and of course- try some apple cider donuts.
42W813 Reinking Rd, Pingree Grove, IL

Through Nov. 30: “The Flowers of Monet,” at the Garfield Park Conservatory

Can you smell it from here?! The Garfield Park Conservatory has transformed its Artist’s Garden into a real life replica of some of Claude Monet’s famous works of art his flower paintings. Come experience this once in a life comparison. 300 N Central Park Ave, Chicago 60624

More from Better:


Alexis Miller recently graduated from the University of Wisconsin-Milwaukee where she earned a degree in Journalism, Advertising & Public Relations, and Media Studies. In her free time, she does Pilates, floral arrangements, and some freelance event planning. As an alumna member of Alpha Omicron Pi, Alexis is an enthusiastic fundraiser for the Arthritis Foundation.