With the Autumn Equinox and Chicago’s breathtaking Chicagohenge spectacle about to grace Chicago, October is upon us and we have a month of our city’s great fall transition ahead.
Rather than looking over our shoulders melancholically at the passing of summer, we can look ahead at what is arguably Chicago’s most beautiful time of the year.
From here on out the city’s aesthetics begin to peak as a hundred shades of autumnal color befall Chicago. The air is cool and crisp, the sun is still warm in the afternoons, and there is plenty of fall fun taking place. Plus, Halloween is hiding around the corner.
From pumpkin picking and spiked ciders to haunted houses and spooky experiences, here is our list of the top October activities to do in and around Chicago!
1. Check out the changing leaves
For many, the most magical part of fall is the changing leaves. October marks the month that autumn shades sweep through the city turning trees and parks from green to crimson.
The first thing to do is bask in this entrancing transition. We’ve picked out 10 of the best spots to view the changing leaves in Chicago for those who can’t get enough of the golden 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!
Read about our best places to see the autumn leaves in Chicago.
2. Pop into Chicago’s largest pumpkin pop-up
With fall’s arrival comes a plethora of pumpkin patches. Our pick of the bunch, and one of Chicago’s most popular Halloween time events, is most certainly Jack’s Pumpkin Pop-Up.
Now open for the season, this celebration of fall is one of Chicago’s most popular October events and also the only one that takes place 100% outside. This year there will be a corn maze, axe throwing, carnival games, food trucks, full bars, and much more, all spread out over 2 acres in Goose Island!
Read more about Jack’s Pumpkin Patch Pop-Up.
3. Lose yourself in Richardson Farm’s ‘world’s largest corn maze’
While at Jack’s Pumpkin Pop-Up, you’ll find the largest corn maze in the Windy City, you only need to travel a little outside of Chicago itself to enjoy the world’s largest corn maze.
Richardson Farm in Spring Grove, Illinois, is home to a 28-acre labyrinth holding the title of the world’s largest corn maze, and this year it’s paying homage to none other than the terrifying dinosaurs of the Jurassic Park franchise.
As well as the 9-10 miles of maze trails, Richardson Farm is also home to a huge pumpkin patch where you can eat, carve, or smash giant pumpkins as well as throw them off of a giant 50-foot observation tower. You’ll also find plenty of Halloween thrills this month in addition to a zip line, zorbing, a petting zoo, a giant slide, and much more!
Read more about the Richardson Farm corn maze.
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-Lanterns, for 10 spooky nights of October.
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 more than 1,000 hand-carved pumpkins — with some weighing up to 150 pounds!
5. Check out Navy Pier’s all-new Halloween experience
Of course, as we mentioned, another highlight of October is Halloween. All manner of Halloween events and activities offer consistent frights throughout October but this year Navy Pier adding an all-new experience to the mix.
The immersive “Garden of Decay” will premiere at Chicago’s Navy Pier on Friday, October 13 featuring immersive theater and astounding art installations.
Read more about Navy Pier’s new Halloween event.
6. Test your fortitude at Chicago’s 13th floor haunted house
If you’re looking for a real thrill this Halloween season you’ve come to the right place.
Rated as one of the Top 5 Haunted Houses in the U.S.A. by USA Today, 13th Floor Haunted House Chicago has officially returned from the grave for its terrifying 10th season in Chicagoland to add some fuel to your nightmares!
Set amongst forty-thousand square feet of fun at 5050 River Road in Schiller Park near the Rosemont entertainment district, the new site features two all-new, scary-as-hell exhibits entitled The Deadlands and Depths of Darkness.
Read more about 13th Floor Haunted House Chicago.
7. Brave the Midwest’s only haunted house inside an actual abandoned prison
For those interested in going the extra mile in search of terror and trepidation, the 13th Floor Entertainment Group is also behind the blood-curdling haunted house experience at Joliet Prison.
The Midwest’s only haunted house inside an actual abandoned prison is sure to have your heart pumping if you’re prepared to head out to the huge Joliet Correctional Center outside of Chicago.
After an inaugural Halloween experience in 2021, 13th Floor Entertainment Group, has again transformed the old prison and reopened it to the public for its third year with an even more eerie array of experiences within the spookiest of settings.
Located in the annex building at 401 Woodruff Road in Joliet, the breathtaking haunted house has opened with two attractions – The Abominations and Tormented – all for the price of one ticket.
Read more about the Old Joliet Prison Haunted House experience.
8. Venture out to “Second Salem”
If you are fascinated by the tales of purportedly haunted places, get a buzz from exploring abandoned buildings, and wish to celebrate this Halloween with more than a costume party, adventuring to a real-life ghost town might be for you. A hair-raising reality awaits just under two hours away in the town of Whitewater.
Nicknamed “Second Salem” after the notorious town near Boston renowned for its 1692 witch trials and subsequent executions, Whitewater in Wisconsin has its own repertoire of creepy tales associated with witchcraft. We’ll let you read and decide if you’re prepared to brave it.
Read more about the haunting history of Whitewater.
9. Send your senses soaring with a Dining in the Dark experience
I slightly less spooky experience, yet still an unforgettable adventure can be found in the form of Dining in the Dark experiences.
Take your date night to the next level or embark on a surreal experience with friends by sitting down for a meal blindfolded to focus on more important things like the exquisite food and wine that make up a secret menu. Engage your taste buds to their maximum as you indulge in a delicious three-course meal like you’ve never done before.
Grab tickets to Dining in the Dark with Wine Service: A Unique Blindfolded Dining Experience.
10. Eat pizza from one of the best pizzerias on the planet
Talking of memorable meals, a local Chicago Pizzeria was recently ranked one of the best pizzerias in the world at an awards ceremony hosted at the Teatro di Corte in Naples, Italy.
Describing itself as “a casual spot with Neapolitan-style thin-crust pizzas served in a rustic space with patio seating” Spacca Napoli Pizzeria was the only place in Chicago to make the list and one of a handful from the United States.
There’s never been a better excuse to eat pizza!
Read more about Spacca Napoli Pizzeria.
11. Learn how to make Neapolitan-style pizza
Put your chef’s coat on and join TreeHouse Pizza Chef, Marco Colin, for an intimate and fun pizza-making and wine-tasting event! Set in a private Italian-coast-inspired back room and outdoor patio, you’ll be in the perfect scene for the task.
Whether you’re an expert or just starting out in the art of pizza-making, you’ll have an incredible time. Get your tickets now for Treehouse Chicago Pizza-Making and Wine Experience in Chicago!
Grab tickets to a Chicago pizza-making and wine experience.
12. Check out this Quinceañera comedy show experience with dinner by Broadway’s Rick Najera
If you’ve ever wanted to attend a Quinceañera, now’s your chance! Spend the evening enjoying the comedy show, dancing, dinner, and drinks! Sweet 15 takes you inside a Quinceañera that is part comedy play and part immersive experience with cocktails, dancing, and dinner. Written by Rick Najera, a Broadway playwright and award-winning Hollywood screenwriter known for his work on TV shows like “In Living Color” and “MAD TV,” Hulu’s Emmy-nominated “East Los High,” and films such as “Nothing Like the Holidays,” which starred actress Debra Messing.
13. Sip a Guinness at the incoming Guinness Taproom
In other big news, for anybody who loves Chicago beer and has a thirst for that smooth, creamy, world-famous Irish dry stout, you’re in luck! Chicago’s long-awaited Guinness Taproom has opened just in time for October.
The Ireland-based brewer finally opened the 15,000-square-foot Guinness Open Gate Brewery Chicago in West Loop on Thursday, September 28 offering a unique new experience in one of Chicago’s most exciting neighborhoods.
Read more about the Guinness Open Gate Brewery Chicago.
14. Check out the new Federales
Another new opening in Chicago is the new 8,500-square-foot Federales in Logan Square. The sprawling party bar has opened in the northwest neighborhood with a retractable roof replacing the family-owned Father & Son Pizza.
It is now only the second establishment with a retractable roof after the Asian Brewpub Beyond Bixi Beer at 2515 N. Milwaukee Avenue.
8,500 square feet inside and 2790 square feet outside offer a modern industrial hideout with a retractable roof that transforms it into an urban oasis while murals covering both indoor and outdoor spaces have been created by Jason Botkin in collaboration with local artists Erik Lundquist and David Alvarado.
Read more about the new Federales Chicago location.
15. Kick back at the new vegan food hall
In slightly healthier news, PlantX has turned its Uptown outpost into a huge 6,500-square-foot vegan food hall. Known as XMarket Vegan Food Hall, it is being touted as the largest vegan food hall in the Midwest and will feature an all-vegan convenience store, a bar with vegan wine, a coffee shop, and more.
Read more about XMarket Vegan Food Hall here.
16. Spend a Sunday at Maxwell Street Market
Maxwell Street Market, Chicago’s longest-running open-air market, which first debuted back in 1912, is currently enjoying its 111th year in Chicago.
Open every Sunday at 800 South Des Plaines Street from 9 am to 3 pm through to Sunday, October 29; shoppers can expect a Sunday of spirited live music and sensational street food as well as an eclectic array of bric-à-brac including handmade crafts and undetected treasures.
Read more about Maxwell Street Market.
17-22. Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series is providing an array of breathtaking spectacles in the Windy City. Talented musicians will be performing at extraordinary venues all over Chicago offering guests the chance to marvel at the enchanting combination of flickering candles and melodic sounds.
Here are some of our favorite Candlelight concerts taking place this month:
- Candlelight Aurora: A Tribute to Taylor Swift at Stan Mansion on Thursday, October 5
- Candlelight: The Best of Zelda at Stan Mansion on Friday, October 6
- Candlelight Flamenco: A Journey Through Spain at Arts Center of Oak Park (Free Church) on Friday, October 13
- Candlelight: A Haunted Evening of Halloween Classics at Cafe Brauer on Wednesday, October 18
- Candlelight: A Haunted Evening of Classical Compositions at Bohemian National Cemetery on Friday, October 27
See the full list of candlelight concerts in Chicago here.
Can’t decide on a concert but want to ensure you attend one or need to buy a gift for somebody special? Candlelight gift cards are easy to use and valid for any Candlelight event in the U.S., making it a unique gift for friends and family.
23. Grab cheap movie tickets to any Regal cinema in Chicago
We’re in a peculiar age of independent movie theaters often closing due to a lack of customers and simultaneously many people feeling it is all the more affordable to watch a movie at home and forego the enhanced cinematic experience to save a few bucks.
The solution to this is simple: discounted theater tickets, and now Regal Cinemas are offering all the amenities and bonuses of a multiplex screening for a cut price to make going to the movie theaters comfortable and affordable once more.
Read more about cheap Regal cinema tickets.
24. Watch a movie screening at the Rooftop Cinema Club
Comprising rooftops with city views over sweeping skylines, the materials for a perfect viewing experience like state-of-the-art wireless headphones and adjustable deck chairs, plus, of course, a huge screen showing iconic movies, Rooftop Cinema Club provides what it calls the “ultimate open-air cinema experience.”
Already operating across the country in places like New York, Miami, and Los Angeles, the London-based company branched out to Chicago last year, premiering up on the fifth-floor terrace of the Emily Hotel in the heart of Chicago’s former warehouse district of Fulton Market.
The top-rated boutique hotel is now showing several movies a day for its one-of-a-kind outdoor cinema experience and features a weekly lineup of cult classics, timeless comedies, and recent releases projected onto its state-of-the-art LED screen.
Check out the full schedule of movies showing at Rooftop Cinema Club in October.
25. Check out the Steve McCurry exhibition
Steve McCurry is one of the most influential photographers of our time with a lengthy career that has spanned three decades. With much excitement, it was just announced that his iconic photographs are coming to Chicago this fall after touring Madrid, Mexico City, Lisbon, and Sydney.
Tickets will be released on October 4th at noon before the exhibition officially opens on October 19th, so be sure to join the waitlist now to get early access to tickets as soon as they are released to the public!
Read more about the incoming Steve McCurry exhibition.
26-28. Enter a Chicago museum for free
Free admission days are somewhat of a rarity during the summer months when Chicago’s tourism industry is thriving. Luckily though, as we enter the fall months many of our marvelous museums and attractions begin bringing back frequent free admission days.
This September Shedd Aquarium, Field Museum, AND the Museum of Science & Industry are all offering free midweek days.
Check out our full guide to free admission days at Chicago’s many museums and attractions.
29. Indulge your artistic side at Chicago’s Museum of Contemporary Art
While not free, another standout museum from Chicago’s plethora of world-renowned museums is the Museum of Contemporary Art. This unique, grand structure houses exciting temporary and permanent exhibitions that are sure to leave you awestruck.
Make it a whole family day and prepare for an unforgettable experience in contemporary art or gather a group of friends and embrace your whimsical, artistic nature as you explore the fascinating collections. Filled with endlessly intriguing paintings, sculptures, and photos, this museum is always one for the books.
Read more about reduced tickets at the Museum of Contemporary Art.
30. Get free entry to Adler Planetarium on a Wednesday
Another of Chicago’s famed attractions, The Adler Planetarium, underwent a huge revamp during a two-year Covid-19-induced hiatus and now boasts a brand new telescope in the Doane Observatory, which holds the title of the largest public telescope in the state.
As well as a new observation park, the planetarium has a shiny new roof giving the 80-year-old dome an iconic new glow. However, The best news is that upon its reopening, the planetarium announced that Illinois residents would be able to enter for free every Wednesday evening from 4-10 pm for the foreseeable future, provided they bring proof of residency.
Read more about the Adler Planetarium.
31. Wander Morton Arboretum’s new range of sculptures
A new exhibition at the Morton Arboretum has opened earlier this year featuring a collection of towering arbor-inspired sculptures.
Titled “Of the Earth,” the exhibition features five exclusive new works from Polish-American artist Olga Ziemska and replaced those on display for Human + Nature.
The largest exhibition of artist Olga Ziemska’s work to date, “Of the Earth” is has been created exclusively for Arboretum visitors. According to an official Morton Arboretum release, Ziemska’s sculptures have been predominantly created from reclaimed tree branches and other natural materials gathered from various locations throughout the Arboretum’s grounds.
Read more about the arboretum’s ‘Of the Earth’ exhibition.
32. See Art on the MART’s fall projections
Of course, you don’t need to enter an exhibition to see extraordinary art in Chicago. Holding the title of the “largest permanent digital art projection in the world”, Art on theMART attracts thousands to the Riverwalk and Wacker Drive in downtown Chicago every week from spring through fall by transforming the 2.5-acre river façade of the Merchandise Mart.
The new fall program features mesmerizing projections developed in response to humanity’s environmental crisis and the power of AI technologies which will be shown every night from 7:30 pm to 8:30 pm through Friday, November 18.
Read more about Art on theMART’s fall schedule.
33. Peruse the magnificent street art murals of Chicago
Chicago’s street art and graffiti scene has continued to thrive in Chicago over the last decade. New pieces pop up all over the city every week, some of which are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now part and parcel of the Windy City’s identity.
Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for racial equality, celebrate different heritages, and honor the essential workers of our societies during turbulent times.
Hunting down the must-see street art murals in Chicago is a rewarding experience any time of the year and luckily we’ve rounded up our top murals in the city so you can navigate your way around the best of the best and learn about the inspiration behind some of Chicago’s famous murals.
View our list of the 25 most amazing murals in Chicago.
34. Unleash your inner artist at a Spray ‘N’ Sip urban art workshop
If perusing Chicago’s incredible street art has your creative juices flowing there’s no better place to let your inner artist run wild than at Chicago’s incredible BYOB Urban Art Workshops.
Taking place weekly within Studio W.I.P. at The Chicago Kedzie Plaza, there’s no pressure and no presumptions, just creativity and fun flowing in all forms.
Trained professional artists will teach you the tricks of the trade as unleash your inner artist on a mural with your favorite drink in one hand and a spray can in the other.
Grab your tickets to a Spray Paint ‘n’ Sip Urban Art Workshop.
35. Have a Pumpkin Patch Shake at Jojo’s Shake Bar
On your gallivanting between murals this fall, you can do worse than stopping by Jojo’s Shake Bar for a Pumpkin Patch shake.
Famed for its over-the-top milkshakes and biggie hot chocolates, Jojo’s Shake Bar will once again elaborately deck out its adjacent patios in the heart of River North and Naperville with hay bales, hundreds of pumpkins, and some exceptional fall photo ops.
Visitors can feast on gourmet caramel apples, pumpkin & apple pies, spiked ciders, and biggie hot chocolates & of course, their notorious shakes. If you’re a fan of those over-the-top milkshakes down at JoJo’s Shake bar make sure you don’t miss out on their Famous Pumpkin Patch Shake. The one-month-only special comes topped with a pumpkin pie slice, a taffy apple, roasted marshmallows, and a toffee pretzel.
Read more about Jojo’s Shake Bar.
36. Sip on some spiked cider
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 (a 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.
You can find our list of Read about where to get hard apple ciders.
37. Play soccer in the sky at Chicago’s first-ever rooftop soccer pitch
Much to the excitement of soccer fans all around the city, an exciting new soccer venue opened in Chicago last year taking the city’s soccer scene to new heights.
Located atop the NEWCITY parking structure in Lincoln Park, the Skyline Pitch opened as “Chicago’s 1st rooftop soccer venue for guests of all ages to train, play, and celebrate the game of futsal and soccer with an unmatched view of the beautiful Chicago skyline.”
First thought to be a temporary fixture, the skyline pitch and its variety of leagues will run for a few more weeks offering an unforgettable experience high in the sky.
Read more about the Skyline Pitch in Chicago.
38. Play pickleball at Grant Park’s brand-new courts
Pickleball, the nation’s fastest-growing sport, is rapidly taking over Chicago with a seemingly unstoppable influx of new courts offering places to play all over the city.
After Big City Pickle branched out from Goose Island and Gold Coast to Fulton Market with an initial 9 new pickleball courts this summer, Grant Park has now followed suit.
Thanks to a huge $500,000 grant from Lollapalooza organizers C3 presents, City officials and members of the Grant Park Advisory Council last week unveiled 16 new pickleball courts in southern Grant Park along with six refurbished tennis courts that were revamped after years of usage for festival parking.
Read more about the new pickleball courts.
39. Hit up the largest outdoor adventure park in America
For even more taste of the action, take a short drive down to Lemont, where The Forge: Lemont Quarries offers an all-around day of fun.
From mountain biking and climbing walls to yoga to a tactical laser tag course, the 300-acre park is packed with everything you can think of with something for everyone!
Read more about The Forge: Lemont Quarries.
40. Brunch to your heart’s content
If you’re in need of an instant mood boost, searching for a group Sunday Funday activity, or looking to cure a hangover from the night before, brunch is the solution to all problems.
Luckily Chicago has an abundance of seriously good morning eats, and here we’ve compiled the best of the bunch!
Read our full list of the best brunch spots in Chicago.
41. Sample the best cocktails in Chicago
Whether you’re treating yourself to brunch in Chicago, kicking back on a Chicago patio, or enjoying drinks out at one of Chicago’s many bars and restaurants, you can be sure a finely-crafted cocktail is only seconds away.
From top-notch margaritas to more innovative cocktail concoctions and everything in between, the Windy City and its abundance of revered mixologists have the answers to whatever it is you’re after.
We’ve recently filtered through the noise to round up the best cocktail bars in Chicago based on our experiences at Secret Chicago, our reader’s most popular choices, and a scrupulous assessment of settings and drink quality.
Read our full list of the best places to buy cocktails in Chicago.
42. Kick back at a revered brewery
If craft beers are more up your street than a fruity cocktail, worry not, for Chicago has an abundance of internationally acclaimed breweries.
Frequently recognized as one of the best beer cities in the country, our seasoned and inventive beer scene has produced so many fantastic breweries and taprooms in Chicago that we’re spoilt for choice.
There are now over 200 breweries, big and small, across Chicagoland, meaning there are plenty of opportunities to enjoy a finely crafted beer in a range of different environments, whatever the weather.
To make sure you’re checking out the best of the best, we’ve here rounded up the 10 best breweries, brewpubs, and taprooms in Chicago. Cheers!
43. Buckel up for a Drunk Shakespeare show
On the topic of booze, another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show.
On a stage in a hidden speakeasy behind the Chicago Theater, guests will find a glam cocktail bar and library with over 10,000 books. Five classically-trained actors meet as members of “The Drunk Shakespeare Society.” One of them has had at least five shots of whiskey, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Hilarity and mayhem ensue while the four sober actors try and keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Grab tickets to a Drunk Shakespeare show.
44. Chuckle away at Chicago comedy show
If you’re looking for a chuckle, there’s no place better for that than at a Chicago comedy show. Famous for its production of funny guys and girls. Chicago has some of the best places to see a comedy show in the country.
At Laugh Factory Chicago, some of today’s biggest names and local comedians are delivering something for every taste and style throughout the year.
Grab tickets to a show at Laugh Factory Chicago.
45. Go apple picking
While we’ll miss the blooming gardens and sunflower fields of summer, we’re excited for the changing leaves, pumpkin patches, and orchards to harvest the fruits of fall. The peak season for apple picking starts rolling from the end of September through October.
If you want to take measures into your own hands, head to our article on the best places to pick apples in Chicago to find out where to get your pick of the season’s best apple batch.
Read about the best place to pick apples near Chicago.
46. Go hiking near Chicago this fall
Every season offers new and different ways to enjoy nature, with spring splashing with the newly melted snow, summer peaking with an abundance of colors, fall trees bursting with warm red and golden hues, and winter bringing a clean slate of snow to remind us the year as come to a close.
No matter the time of year, there are plenty of great for hiking near Chicago but it is during fall that many offer a particularly unique spectacle.
As the autumnal hues set in across the Land of Lincoln, escape from the city for a day getaway by exploring nature and hiking at one of the esteemed parks near Chicago.
47. Head out of the city and see Illinois’ natural spectacles
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible spectacles this time of the year.
From monolithic marvels to cascading waterfalls, we’ve rounded up the 7 natural wonders of Illinois that you can visit while they’re about to peak so you can plan an outing regardless of whether you want to hike or not.
Read our full breakdown of the 7 Natural Wonders of Illinois.
48. Stay in a Starved Rock Getaway cabin
One of the aforementioned spots, Starved Rock State Park, has recently opened a selection of minimalistic cabins with floor-to-ceiling windows allowing guests to wake up fully immersed in the wilderness.
Located in lush landscapes and with minimalistic yet comfortable designs, they offer the perfect escape for those wanting to disconnect from busy city lives with restorative stays in the middle of nature.
Undoubtedly one of our state’s most impressive natural spectacles, Starved Rock offers over 13 miles of hiking trails, numerous cascading waterfalls, and 18 different canyons.
49. Discover the Windy City’s small pockets of Eden
Of course, Chicago is no far friend from nature and there are many places you can get back in touch with Mother Nature all over the city.
The Lakefront, lush parks, and incredible hiking trails offer great natural experiences but Chicago also has numerous secret gardens hidden across the city.
Read our full article on 10 of the best spots around the city.
50. Secure a spot at Chicago’s upcoming light shows
Okay granted, the last recommendation isn’t strictly for October, but we heavily advise you to get booking tickets to Chicagos light shows coming up in November. Chicago has some of the best in the country but many of them sell out fast!
Morton Arboretum, Chicago Botanic Gardens, and Lincoln Park Zoo are just a few that guarantee an extra special festive spectacle. With each respective light show event starting up in November it’s this month that tickets go on sale and we recommend snapping them up quickly!
Read more about Chicago light shows.
[Featured Image from Unsplash]