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Things To Do

60 Freakin’ Awesome Things To Do In Chicago This October

By Colby Smith

60 Freakin’ Awesome Things To Do In Chicago This October

We’re flipping out for fall!

It’s officially autumn and here in Chicago we couldn’t be happier. The air is cool and crisp, the sun is still warm in the afternoons, and the leaves are 100 shades of dazzling. Plus, Halloween is hiding around the corner. While, no doubt things are different this year, there are still bountiful things to do in Chicago this autumn to enjoy! [Featured image: @jamielinkphotography]

1. Walk The Yellow Brick Road In A Wizard of Oz Burlesque Experience

Starting off our list is a multi-sensory experience that is not to be missed. With Coronavirus restrictions sweeping the country one place you’ll be spending a lot of time is your own home. The Dark Side of the Boob: A Wizard of Oz Burlesque Experience offers stimulation for all five senses that has now been digitally mastered for your home screen. The immersive experience brings the best of Chicago’s nightlife entertainment to your living room with audio synthesizing to Pink Floyd’s classic hits. Audiences transport themselves in a psychedelic tornado to the wonderful world of Oz. Get tickets to the unique streaming show here.

2. Go Down The Rabbit Hole For The Mad Hatter’s (Gin &) Tea Party

The Mad Hatter is bringing his infamous gin and tea parties to Chicago! In this immersive, theatrical cocktail experience you’ll enjoy a menu of delicious Rabbit Hole Bespoke Gin concoctions in the most psychedelic of settings. Costumes are welcome, but if you don’t have time to put an outfit together don’t worry— the Hatter will be lending out some of his craziest hat creations! Want a seat at the tea party table? Get your tickets here! ⭐️Sponsored⭐️

3. Pop In To A Horror Pop-Up

While 6th Dimension Space’s Horror Museum could simply rig a TV set in the middle of an empty room tuned into any given news outlet to instill fear, the space is taking the extra step to scare your pants off in mid October. The two-story exhibition will feature countless real-world stories taken straight out of Stephen King’s worst nightmares: demonic possessions, paranormal encounters, witchcraft, and tales of folklore.

4. Lurk In The Light Of 1,000 Jack-O-Lanterns

This year, the Chicago Botanic Garden is going full Tim Burton with their Halloween event, Night of 1,000 Jack-O-Lanternsfor 10 spooky nights starting October 14! Even though you won’t be able to eat any of the pumpkins on display at Chicago Botanic Garden’s Night of 1,000 Jack O’Lanterns, you can still admire the brilliant intricateness of the many many hand-carved pumpkins — with some weighing up to 150 pounds!

5. Dine In The Dark

Imagine. You’re seated at a table in a room shrouded in darkness. You tremulously reach for your glass. It’s all too eerie, but the first of three courses has just been served — seemingly out of thin air — and already your senses are reeling. There’s an air of ominousness, but your taste buds have never been this heightened before, and with food this tantalizing, you can’t leave. This is the Haunted Dining in the Dark experience.

6. Experience Gorgeous Outdoor Candlelight Concerts

You can still experience an absolutely magical (and safe) fall here in Chicago, and part of that is thanks to the amazing outdoor spaces the city has to offer. For one final month, Fever Originals is bringing its wildly popular Candlelight concert series to open-air venues for the season, from stunning rooftops and terraces to enchanting secret gardens.

7. Slay The Competition At Old Grounds Social’s Drag Bingo Night

Have the past few months been a little less-than-dazzling? We feel that. To put a little sparkle back into our lives, the queens over at Old Grounds Social are hosting Drag Bingo on Thursdays with dancers, prizes, drink deals including $20 domestic beer buckets, $25 champagne buckets, and shot specials throughout the night for a fabulously fun time!

8. Discover The Beautifully Multi-Faceted Female Experience

WOMANISH is a small business relief fund that is seeking to raise $1 million in order to provide micro-grants to female-owned local businesses in Chicago that have been negatively affected by the COVID-19 virus. WOMANISH is accepting applications for qualifying businesses, wherein businesses can apply here. At this moment, WOMANISH has currently raised over $10 K, if you want to get that number up, you can donate here! Or, you can check out their epic 5-story wonderland and explore the experience of a woman through their beautiful art installations that affect 10 unique female perspectives!

9. Howl At The Moon

While plans on the ground have taken a scary turn and most major Halloween events have been canceled, nature will be stepping in to put on a spooky show of its own. If you’ve ever wondered how the saying “once in a blue moon” came about, it was coined from the unique celestial phenomenon where we get two full moons in one calendar month or the third of four full moons in a season. The second full moon in a month (or third of the season) is called a Blue Moon. This happens every two to three years and the next one is happening on October 31, 2020.

10. Bring Your Painting Skills To Life

The 1.5 hour course is led by an expert artist to guide you through the creation of a painting inspired by the Dias de Muertos. Release your creativity while painting along. No experience needed! List of recommended supplies: a canvas or canvas board, a big brush, a skinny brush, a water cup, paper towel, a plate, a pencil and an eraser, paint (blue, yellow, red, black, and white), and an apron or painting clothes.

11. Shoot Zombies With Lasers

Photo credit: @theforgelemont

The Forge: Lemont Quarries just outside of Chicago is loaded top-down with action-packed entertainment for anyone and everyone to enjoy. With Halloween around the corner, the park has unleashed a Zombie Apocalypse laser tag game that’s out of this world. Don’t take from us though, get word straight from the source:

“Adventure comes in endless forms at The Forge: Lemont Quarries and our tactical laser tag arena is the perfect example,” the park writes on their website.  “Playing tactical laser tag is a great way for people age 8 and up to experience the thrill of simulated combat experience without the pain and added expense of paintball.  Experience hyper-realistic sound effects while playing with military-grade replica weapons in small teams or large groups.”

12. Pull Into A Drive-Thru Haunted House

If you heeded your parents’ advice as a child to never wander into dark alleys, then buckle your seatbelt because this drive-thru haunted house experience is about to take you for a ride! On October 2, Replay in Lincoln Park will debut its drive-in haunt, Alley of Darkness:

“Our haunt is set in an alley in the shadows of the Red Line where a horrible incident occurred not long ago,” Replay has written on the event. “You’ll first settle in with a drive-in movie experience that sets the narrative. The undead, demons, zombies and more jump out at and rock your car accompanied by sound effects and sprays of blood. That’s right… your car gets covered in blood.”

13. Walk With Ghosts

They wrote the book(s) on Chicago ghosts! Now they are in their 18th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago’s haunted history over more than two decades. Chicago Hauntings is the original Chicago ghost tour and still the best. These tours are based on all original research, unlike the many other knock-off tours you’ll find today. Beware of the imitations. Imagine walking in the steps of Chicago’s most notorious criminals at the city’s original courthouse, putting your fingers into actual bullet holes from Chicago’s gangland days, feeling the haunting presences near the site of the old Cook County gallows, and gazing upon the waters where 844 souls lost their lives in the horrific Eastland disaster of 1915. Come along and experience all this and more!

14. Pick Out A Pumpkin

Is there anything more representative of the fall season (outside leaves) than the pumpkin? Whether it’s sipping on a pumpkin spice late, digging into pumpkin pie, or re-reading instructions on how to properly carve a jack-o-lantern, the pumpkin is (literally, in the latter case) the face of autumn. Eat it, carve it, or smash it, get your hands on one of your own at one of these bountiful pumpkin patches around the Windy City.

15. Freak Out Your Friend

Scare Your Friend is a bundling of two of Psycho Clan’s wildly popular blindfolded haunted houses – The Empty Place and A Dark House. Now, they are available to the public as audio downloads that come with digital how-to manuals that guide you in staging these unique horror experiences safely in the privacy of your own home! Your personal surroundings and your own imagination will bring the whole experience alive. Both shows can be done at home and should be done either with one other person or with small groups of people who you live with or with whom you have formed social cohorts. You can share the download up to 20 times! If you are tired of participating in virtual experiences on a screen, this is safe…but will raise the hair on the back of the neck. This is a Halloween treat (or beyond) that gets you up and on your feet!

16. Roam The City For Lost Spirits

Chicago is an enchanting city, perhaps, more enchanting than you might hope. With a complicated history rife with tragedy, the city’s spiritual underbelly finds a way to show its ghostly face to unsuspecting witnesses. Meet the local ghosts in your neighborhood with this list of the 10 most haunted places in Chicago.

17. Trip Into A Haunted House

Remember when haunted houses were simply makeshift stages at your neighbor’s? Some of the parents would string up a few cotton cobwebs, black curtains, and maybe one of the dads would dress up as a vampire, and do that one laugh? Well, those days are long and gone. Not only is the world itself a more terrifying place to be, but haunted houses have gone to hell and back to scare the absolute bejesus out of you.

18. Kick Back With Playful Goats Then Hit A Rooftop For A Craft Beer Tasting

Some days you just need some one-on-one time with a pasture full of adorable goats, you know? Experience the pinnacle of wholesomeness by hanging out with the billy kids over at GlennArt Farm and afterwards, double down on those warm fuzzy feelings with a few flights of delicious craft beers on the rooftop of One Lake Brewing for this exclusive Brews n ‘Baahhs’ beer tasting experience!

19. Sip On Some Spiked Cider

Photo credit: @caferobey

There are two top contenders vying for the title of the true fall drink: the pumpkin spice latte and hard apple cider. While the former has pumpkin (big plus) and caffeine, the latter has alcohol — a slight advantage, we’d say. Get your fill of all the warm fuzzy feelings of fall by visiting one of these watering holes for a cup of spiked apple cider.

20. Meet The Pumpkin Dinosaur

If you’re like one of us and whole-heartedly embrace everything autumn, you’ll want to take a short trip down to Goebbert’s Pumpkin Patch, where they’ve got tons of seasonal attractions for the whole family, including a pumpkin-eating dinosaur!

21. Go On A Haunted Pub Crawl

Bad news, Chicago, evidently we’re one of the most haunted cities in America. Bars, buildings, parking lots, theaters — all possessed by undead spirits dating back to the 1800s. Nightly Spirits gives you the opportunity to meet your incorporeal neighbors while unmasking the freaky history that plagues the local neighborhood. But keep your spirits up, the tour also makes a number of boozy stops at local haunts along the way.

22-24. Scream Your Head Off At A Drive-In Movie

It’s official: 2020 is cursed. But Chicago’s 90-year-old independent cinema, Music Box Theatre, is making the most of it with a treat for horror fanatics. Throughout the entirety of October, the theatre will be overtaking the Chi-Town Movies Drive-In with a 31 Nights of Terror drive-in series!

  • Fright Night brought to you by PR Pop-Ups is a one-of-a-kind Halloween experience! This drive-in experience includes costumes, candy, food trucks, a bar, and a double feature drive-in movie. Parking spots are first come – first serve, doors open at 7 pm for the first movie. You will have your own private socially-distant parking spot to enjoy the event. You may sit in a lawn chair outside, in front of your vehicle. You may also sit in the bed of your truck or in the back of your vehicle with your hatch open. A Pop-Up Drive-In allows you to be able to safely practice social distancing and still enjoy a sense of community. Bring the whole family, bring your mask, and enjoy the experience.
  • Join the crew at PR Pop-Ups at the all-new Cross Pointe Park come out and enjoy the nostalgia of a Drive-In Movie close to home. Bring the whole family, bring your mask, and enjoy the experience. There will be a food truck and bar on-site. However, you can bring your favorite food/snack and non-alcoholic beverages from one of the town’s great local restaurants. Have your own private, socially distant spot to enjoy the movies. You may sit in a lawn chair outside, in front of your vehicle.

25. Pop In To A Pumpkin Pop-Up

Fall has officially landed in Chicago and with it, Jack’s Pumpkin Pop-Up. This celebration of fall is one of Chicago’s most popular Halloween-time events. It’s also the only one that takes place 100% outside. Last year there was a hidden bar for you to reward yourself with a hard cider or Tito’s cocktail after making it through the corn maze! While the pop-up has yet to release its official opening dates, Jack’s has announced its official return on social media.

26. Celebrate Black-Owned Restaurants For Blaktober Fest

Photo credit: @andysunflowercafe

From the minds behind Black People Eats restaurant directory in Chicago comes a fresh new food festival entitled, Blaktober. Throughout the month of October, a number of participating Black-owned restaurants across the Windy City will be offering numerous specials and dish deals.

27. Honor The Late Justice Ruth Bader Ginsberg At The Illinois Holocaust Museum’s ‘Notorious RBG’ Exhibition

The Illinois Holocaust Museum in Skokie opened an exhibition earlier this year, Notorious RBG: The Life and Times of Ruth Bader Ginsburga detailed showcase of Justice Ginsburg’s life, career, and internet phenomenon. The interactive exhibit not only celebrates the groundbreaking work of RBG, but educates people about sexism, civic engagement, prejudice, and gender equity. “Few people convey these lessons more vividly than Ruth Bader Ginsburg,” said museum CEO Susan Abrams.

28. Dine In A Dome

Photo credit: @citywineryriverwalk

With the coming of the autumn equinox, so begins the fall season. As the city anticipates colder days ahead, so has it begun to search for inventive solutions to encourage continued outdoor dining. City Winery on the Chicago Riverwalk, in this regard, has been ahead of the game. Last year, the winery features a series of transparent domes on its patio, and on October 1, they’re coming back.

29. Enjoy A Magical Afternoon At The Park With Open-Air Theater Performances

Photo credit: @Midnight Circus Facebook

Better enjoy the crisp cool air while you can before winter shows up on the city’s doorstep. If you’re looking for a way to spend a pleasant afternoon, why not a stroll in the park? Better yet, why not interlude that stroll with a free, open-air theater performance?

30. Embark On A Quest For Giant Trolls At The Morton Arboretum

Photo credit: @discoverdupage

The Morton Arboretum is home to a cornucopia of gardens, collections, and natural exhibits for Chicagoans to explore. Additionally, the Arboretum is also home to 6 gigantic trolls lingering in hide-aways to protect its wooden areas. The legend of The Arboretum goes that the 6 trolls first appeared in its wooded areas in 2018. Designed by Danish artist, Thomas Dambo, using reclaimed wood, the trolls — ranging from 15 – 30-feet high, and one 60-foot long —have remained on the grounds in the protection of its trees.

31. Go Apple Picking

While we’ll miss the blooming gardens and sunflower fields, we’re also excited for the changing leaves, pumpkin patches, and orchards to harvest the fruits of fall. If you want to take measures into your own hands, read on to find out where to get your pick of the season’s best apple batch.

32. Strengthen Your Core And Your Mind With An Evening Of Rooftop Yoga And Meditation

It’s a hectic place right now. We could all use a moment to return to a state of inner peace. Mindful Mondays at Ace Hotel Rooftop will provide a pleasant opportunity for you to center your focus through a yoga flow and meditation session. Attendants will also receive a wellness kit as a takeaway from the experience. Fever will be hosting Mindful Mondays throughout October, come enjoy an open-air yoga experience at this West Loop rooftop.

33. Chow Down On Bottomless BBQ

Chef Josh Scheid will be manning the grill on the patio at Old Grounds Social, cooking a Labor Day Weekend feast! Come eat, drink, and enjoy social distanced fun with your loved ones. This tantalizing all you can eat BBQ will keep you coming back for more and you get to wash down the grub with a complimentary well drink, beer, or White Claw Hard Seltzer! There’s no better way to celebrate Labor Day Weekend!

34-36. Grab A Doughnut

Photo credit: @firecakes

Donuts are a craving that you just can’t shake. Whether it’s your first thought in the morning or your last bright idea of the night, the donut-craving is real. Fulfill your deepest donut desires in the Windy City with our list of donut hole-in-the-walls in Chicago!

37-40. Get In Sports Mode

OGs is known for its bottomless weekend brunch fun, and things just got even better with the return of the NFL! We can’t get rowdy at Soldier Field this year, but this is the next-best atmosphere. Surround yourself with fellow football fans and cheer on da Bears or whichever your favorite team might be, as all of the games will be on the big screens. Beers flowing for 3 hours like at a tailgate, but much cozier and top it off with an order OG’s jumbo wings!

  • Bowlero is a blacklight bowling, retro-inspired hangout powered by interactive arcade games, signature cocktails, an outrageously-delicious menu of oversized shareables, and… nostalgia. Bring your friends, family, or a date out to enjoy a special two-hour bowling package at this upscale bowling alley. Forget everything you thought bowling could be—and experience the kind of epic fun that only happens when you go Bowlero.
  • MLB season is back, and even though we can’t sit in the stands, what better option is there than to cheer on our Cubbies in Wrigley at HVAC Pub?! This music venue & restaurant is the perfect place to catch the game, with both indoor & patio seating just steps away from Wrigley Field! This exclusive package is offered for every Cub’s home game during the time of the game. Come watch the game with bottomle
  • ss drinks and pizza in the heart of Wrigleyville!
  • Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. The journey is 14 miles in total (traversed at a nice leisurely pace) and includes a slice of deep dish pizza, a gourmet brownie (did you know, Chicago invented the brownie?), a Chicago-style hot dog, and a few samples of Chicago’s legendary craft beer!

41. Escape To This Tulum-Inspired Oasis

Summer is on its way out. While we’re chomping at the bit to get into all the apple-pickingpumpkin-patchhorror-movie-marathon action of autumn, we’ll still take any chance we can get to give the summer sun’s its due. If a tropical escape is still on your checklist, dive over to The Diver on River North for a taste of paradise!

42. Go Gung Ho For The Bonsai Collection At Chicago Botanic Gardens

Photo credit: @Chicago Botanic Gardens Facebook

With over 385 acres, nine islands, 27 gardens — including one inspired by French impressionist Claude Monet — and four natural areas, the Chicago Botanic Garden is a prime place to witness the season’s floral fireworks. Among their gorgeous gardens is CBG’s beautiful bonsai collection, presently on display until the end of October.

43. Watch Free Outdoor Concerts And Movies In Lemont At The Largest Adventure Park In North America

Photo credit: @theforgelemont

The Forge: Lemont Quarries, aka The Largest Outdoor Adventure Park in America, will be holding live outdoor concerts and film screenings at their vast open-air lawn venue. Back in July, The Forge opened in Lemont outside Chicago. To point out its key attraction is hard to say, as the 300-acre action park offers countless opportunities for fun and adventure; whether it’s mountain biking, ropes courses, zip lines, tactical laser tag, yoga classes, kayaking, or an augmented reality escape room, The Forge has it and everything in between.

44-47. Get Dinner With A Waterfront View


We may be miles away from the ocean but that doesn’t mean we can still enjoy some top-notch waterfront views. From bohemian hideouts by the river to beachy hangouts by the lake, these 9 stunning waterfront spots are all currently open for outdoor dining with new safety measures in place.

48. Cue The Laugh Track For The Fan-Favorite FRIENDS™ Experience

Created by Superfly X, Warner Bros. Consumer Products, and Warner Bros. Television, this event is bringing the FRIENDS™ set to life with interactive activities, series’ history, merch, and original props and costumes, and a dozen rooms recreated from the hit series! To give you a season preview, here are 9 reasons you can’t miss this experience.

49. Get Lost In The World’s Largest Corn Maze

Richardson Farm’s corn maze is in fact composed of 4 smaller mini mazes weaved together by 9 – 10 miles of meandering walking trails. If you forgot your breadcrumbs at home, don’t worry. The corn maze has multiple checkpoints in addition to three 8-foot-high wooden bridges built-in for you pop your head up over the hedge and coordinate your path as you see fit. If the brief bird’s eye view still doesn’t get you to where you need to go, the maze has perimeter paths allowing for easy exit.

50. Check Out A Museum

Photo credit: @mcachicago

While many museums were gracious enough to stimulate our minds in quarantine with virtual tours of their various expositions, we all know that the experience just isn’t the same as it is in person. Thankfully, most of Chicago’s most illustrious, provocative, and imaginative museums have reopened to the public.

51. Take It To The Rooftop

Chicago Rooftops
Photo credit: @marily_bergeron

From mouthwatering Mediterranean food and absolutely delectable Mexican slow-roasted meats with a side of refreshing margaritas to rooftop yoga with bottomless mimosas, these rooftops have it all (including safe social distancing guidelines)!

52. Spend The Night In An Enchanting Tree House

Photo via Air Bnb

Was there ever a child on this earth that didn’t want to sleep in a tree house? Give into the ambition of your youth with an enchanting getaway to this beautiful garden treehouse Air B&B in Schaumberg, Illinois!

53-54. Feed Your Inner Foodie

Created by 13-time James Beard Award-winning food journalist Steve Dolinsky, this Sunday-only series of tours is based on his book, “Pizza City, USA” and features four different styles of pizzas in less than three hours. Learn about Chicago’s 10 pizza styles, and discover why there’s more to The Windy City than just deep-dish.

  • Try the world’s most expensive PB&J sandwich, “The Golden Goose”, at Chicago’s new family-friendly restaurant PB&J – Pizza, Beer & Jukebox. They curate the classic American sandwich by pulling ingredients from all over the world.
  • This Spirits, Wine and Beer Festival is going to put some fire in your belly! Join Gourmet Expos for fabulous spirits, delectable wines, enticing beers, delicious chocolates and beautiful artisan specialities. You’ll be able to chat to the vendors about their products, and watch pairings demonstrations to let you into some food combo secrets! There’s going to be something for every foodie out there and you’ll leave with some tricks up your sleeve for your next dinner party!

55. Get Back To Brunching

Take in the city at this can’t-miss multi-level brunch experience every Saturday! This ticket gets you 90 minutes of delicious, bottomless mimosas, domestic beers, one brunch entree. Step into this incredible atmosphere with live DJs and college football games playing on the screens. It’s brunch time at Joy District… let’s brunch so hard!

56. Bottomless NFL Sundays At The Dime

There’s no place better for a first round of NFL games on a Sunday morning than the lively sports bar Dime over in Lincoln Park. Fans won’t be able to see any live action over at Soldier Field this year so when we say there’s not a better place to cheer on the Bears we really mean it. With TVs scattered throughout the venue, it’s not just a place to watch the Chicago Bears but somewhere for all your NFL needs. The most tempting part? Some of the best wings in town and bottomless beers on Sundays between 11:30 am and 3:30 pm!

57. Throw A Premium Sports Entertainment Party At The Extravagant Epiphany Suites

Soldier Field isn’t the only stadium closed for 2020. All live sports experiences have banned fans due to covid19 restrictions and with bars and restaurants offering extremely limited capacity Epiphany suites are on hands to save the day and provide a unique, exclusive sports entertainment experience. Be it college football, the Bears, or anything else Epiphany suites are designed with high-end hospitality in mind. Each suite is kitted out with an enormous 75′ flat screen and comes with 2 valet parking passes, a personal suite valet, bathroom attendants, and food & beverage service throughout the game. Package deals are available for groups of 8-10 people and groups of 11-15 people.

58. Enjoy Intimate Live Jazz At Le Piano

In the middle of Le Piano sits a magnificent grand piano where some of Chicago’s most talented pianists come to give intimate performances every evening. Le Piano is a cozy listening room optimized to provide the finest piano listening experience possible. As such, special guests and renowned artists come from all over the world to ply their trade at the eponymous piano. Exclusive packages offer deals on cocktails and dinner as live music softly resonates around you in this cozy, elegant, and romantic venue. While it is predominantly a piano bar, Le Piano offers guests the chance to indulge in incredible music while enjoying a classy dinner with a cocktail, and a glass of champagne!

59. Dig Into A Delightful BBQ Dinner Accompanied By Music And Magic At The Hyde

Hyde After Dark returns with a Music & Magic experience at Hyde Park’s Favorite Speakeasy! Start your evening with phenomenal live Jazz as you make your way through the delightful dishes courtesy of classic American hard-wood BBQ joint Porkchop before enjoying the evening’s entertainment: magnificent magic performed by Mr. Jim Bergstrom. Hyde After Dark invites you to experience an amalgamation of some of the most talented folks in the Windy City on one night of outstanding music, food, and magic. Masks must be worn at this 21+ event and exterior doors will be opened if the weather permits!

60. Check Out The Changing Leaves

If you can’t get enough of the fall foliage, or just feel like doing a cannonball into a big ole pile of crackling leaves, follow the link to discover our favorite places to watch the changing of the seasons in Chicago.

See also: 30 Terrifyingly Fun Things To Do This Halloween In Chicago

Tags: autumn, halloween