60 Fantastic Things To Do In Chicago This October

Elliot McGowan Elliot McGowan

60 Fantastic Things To Do In Chicago This October

We’re flipping out for fall!

With the Autumn Equinox and Chicago’s breathtaking Chicagohenge spectacle now behind us, October is here and we have a month of Chicago in fall 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 month. 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 spectacles, 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. We’ve picked out 10 of the best spots to view the changing leaves 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!

You can see the full list here.

2. Pop in to a pumpkin pop-up

With fall’s arrival come 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. This celebration of fall is one of Chicago’s most popular October events. It’s 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!

You can grab your tickets here

3. 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 13! 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! The event will take place October 13 – 17 and 20 – 24 from 6:30 – 10:30 p.m.

Read more about it here.

4-7. Be captivated by a Candlelight Concert

Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but it is in the crisp air of autumn when the concerts reach their peak. Flickering candles and melodic sounds combine phenomenally creating magnetic atmospheres and some of Chicago’s most unique outdoor settings. When the nights are chilly a wonderful array of concerts in indoor venues offer a delightful refuge.

Some of our favorite concerts taking place this month are:

See the full list of candlelight concerts taking place in Chicago here.

8. Enjoy an intimate live jazz show at Le Piano

When it comes to live music, few places offer a better jazz experience than Chicago. There are so many wonderful places to see live jazz in its rawest form here in the Windy City. Alongside esteemed venues like South Loop’s The Jazz Showcase, and Uptown’s Green Mill Cocktail Lounge, Le Piano has emerged as a phenomenal new jazz hideout.

In the middle of Le Piano sits a magnificent grand piano where some of Chicago’s most talented pianists and jazz performers come to play. Here you will find a mind-blowing musical experience merging dinner and intimate performances. Immersive Live Jazz & Dinner for Two packages now ensure a memorable night of dining, drinking, and the magic of jazz in a truly vivacious venue.

Grab your tickets here.

9. Dine in total darkness at Haunted Dining in the Dark

While candlelit concerts and live jazz at Le Piano promise to delight your ears and eyes, Chicago’s Dining in the Dark experience will send your other senses soaring. Eminent psychologists have long advocated dining in the dark as an amplified way to enjoy food in all of its flavor. At this unique sensory dining experience, you will be treated to a surprise 3-course meal tasting menu in the pitch-black darkness.

You would think that these mysterious experiences sufficiently swindled your senses dining in total darkness but now the popular experience has received an ominous overhaul for the return of its Haunted Dining in the Dark season starting October 13.

Get your tickets here.

10. Book a Sleepy Hollow Halloween experience

Sleepy Hollow Bar: An Immersive Cocktail Experience is taking place now through Halloween and your presence is requested in the Western Woods where they say no sane person should go!

You will find a clearing under the moonlit sky: a spot hidden in the woods overflowing with cocktails, dark music, merriment, and life! As our opening-night guest, we welcome you to enter our tavern and enjoy three gothic drinks. We fine folk may have a gift for you here, as well as Godforsaken games of yore to enjoy at your leisure… perhaps you may even experience the rare touch of the undead. You may have heard the Hollow is a place where blood runs cold, haunted by a warrior without a head and bathed in red. But please, worry for naught! What awaits you is an eve of fantastical joy, in woodlands that are yours to explore!

Get your tickets here.

11-15. Enjoy Halloween events across Chicago

Of course, there are plenty of events going on this Halloween. Chicago knows how to throw a party and the Windy City has a range of Halloween celebrations taking place. Some of our top picks are:

16. Roam the city for lost spirits

Or take matters into your own hands and 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.

Click here for the 10 most haunted places in Chicago and get yourself into the spooktacular spirit!

17. Brave the Old Joliet Haunted Prison Experience

For those interested in a real thrill ride, outside of Chicago the huge Joliet Correctional Center, known colloquially as Joliet Prison, has opened as a haunted house just in time for the 2021 Halloween season and it looks utterly terrifying.

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, this is for you. For there will be few Halloween experiences spookier than a trip to what will be Chicagoland’s first and only haunted house inside a real abandoned prison.

You can read the full article here.

18. Kick back with goats and beer

All those thrills and frights might just have you wanting some downtime and a bit less of those spine-tingling sensations and more of those warm fuzzy feelings. When it comes to warm fuzzy feelings look no further than a wholesome afternoon at Brews n ‘Baahhs’. If there’s one way to relax and let your mind unwind it’s with a pasture full of adorable billy kids followed up by a selection of craft beer.

Grab tickets to Brews n ‘Baahhs’ here.

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19. See a Drunk Shakespeare show

Another brilliant experience taking place this fall comes in the form of a live Drunk Shakespeare show. Taking place on a stage in a hidden speakeasy located 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 5 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 here.

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20-22. Be beguiled by a burlesque show

Drunk Shakespeare shows aren’t the only rip-roaring live performances taking place this fall. A number of fantastic burlesque shows offer an exhilarating night out in Chicago. Featuring world-class acrobats, drag performances, unbelievable stunts, and immersive entertainment, these following burlesque performances are our top picks for this month:

23. Let Blue Man Group blow your mind

Few live performances and scintillating spectacles few can beat the magic of the Blue Man Group. The global entertainment phenomenon has returned to the Briar Street Theatre in Chicago for its 30th anniversary. Known for its award-winning theatrical productions, iconic characters, and creative ingenuity, Blue Man Group performances promise a witty, roller-coaster-paced multisensory spectacle.

Fit for all demographics, be it couples, family, friends, and groups of any shape or form, these visually stunning performances guarantee you’ll be leaving with a grin from ear to ear and a spring in your step.

Grab tickets to these electric performances here.

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24. Unleash your inner artist at a Spray ‘N’ Sip Urban Art Party

If all that color and creativity has your creative juices flowing and 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 Spray Paint ‘n’ Sip Urban Art Workshop.

25-7. Check out a museum

Let’s Survive Forever by Yayoi Kusama – Photo Credit WNDR Museum

If you’re needing some artistic inspiration or just want to check out an exhibition now that museums have returned to their full glory, there are a range of exciting exhibits and events taking place this month. Some of our top recommendations are below:

  • Lose yourself to immersive art at the WNDR Museum. Voted one of the top five immersive art experiences in the country by USA Today’s Reader Poll and it’s an unmissable experience right here in Chicago. West Loop’s 10,000-square-foot WNDR museum is home to more than 20 all-new installations offering guests a fresh, reimagined 2021 experience and a brand-new adventure for those who have visited before.
  • See original and authenticated works associated with, arguably, the most intriguing and talked-about artist in modern history at Chicago’s The Art of Banksy exhibition. The exhibit features iconic works such as ‘Girl and Balloon’, ‘Flower Thrower’ and ‘Rude Copper’ alongside some of Banksy’s lesser-known masterpieces.
  • With around 70 different neon and light-based sculptures, Chicago’s Neon and Light museum is teeming with interactive displays and prismatic photo ops. Running for 8 weeks, the Neon and Light museum will showcase work from a variety of talented digital artists, sculptors, and glass benders through October 31.

28. Lose yourself to Marvelmania before it goes for good

MoPOP Marvel Opening (Photo by Christine Mitchell)

News released early last year sent Marvel fans into hysteria when The Museum of Science + Industry announced dates for their interactive exhibit titled Marvel: Universe of Super Heroes. The much-anticipated exhibition opened in March and will come to an end this month on October 24 rounding up half a year of Marvel madness right here in Chicago.

If haven’t been already we suggest you head down to the Museum of Science + Industry at some point this month and snag a selfie with a real-life superhero at the world’s largest interactive Marvel exhibit. Fans can celebrate Marvel history with more than 300 artifacts, original comic book pages, sculptures, and a whole load of fantastic interactive displays. With costumes and props from Marvel’s record-breaking blockbuster films, there is something for all ages and all different levels of Avengers-enthusiast.

Read more about it here.

29. Go and see the colossal sculptures at Morton Arboretum

The Morton Arboretum’s new massive new arbor-inspired exhibition is running for one year. Entitled Human + Nature, the stunning exhibition features five massive natural sculptures from renowned South African artist, Daniel Popper. It’s the biggest show of his work to date. The massive natural sculptures will tower over various locations across the 1,700-acre tree museum and research center for at least one year, leading guests to areas they may not have explored before.

You can read more about it here.

30. Explore Illinois’ natural wonders while the sun is shining

If the natural spectacles on show at the Morton Arboretum have you craving more of nature and you’re prepared to head outside of the city and into the wilderness during fall, there are some fantastic natural escapes close to hand. Although our state may not boast wonders with the universal magnitude of the Grand Canyon or Yosemite National Park, Illinois is teeming with diverse ecological landscapes and natural spectacles that will take your breath away.

We’ve selected the 7 natural wonders of Illinois which all offer breathtaking natural spectacles a few hours drive from Chicago.

You can find the full list here.

31. 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 to apple pick starts rolling from the end of September throughout 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.

32. 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.

You can find our list of where to get hard apple ciders here

33. Discover the Windy City’s small pockets of Eden

Or course, you don’t have to leave the Windy City to find natural escapes. Chicago is certainly no far friend from nature, there are many places you can get back in touch with Mother Nature right here in 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 to stop and smell the roses here.

34. Try a mystery picnic in Chicago

To spice up any park or garden experience in the city you can book an exciting mystery picnic experience. This self-guided food adventure is the perfect way to explore Chicago’s best neighborhoods and avoid the crowds! Starting with a picnic basket, have fun solving personally curated clues and riddles sent to your smartphone that’ll take you on a journey to collect your special gourmet picnic food bit by bit.

Each clue you solve will lead you closer to your next picnic food pickup and even closer to your final stunning secret picnic spot. You can expect a 3-4 hour all-inclusive stress-free date with this fantastic picnic experience. Grab tickets and select the date here and everything will be planned for you.

35. Learn how to make sushi

While a mystery picnic in the park makes for a memorable date while the autumn sun shines, for those days Chicago’s weather is temperamental making your own sushi offers another fantastic alternative date.

In this hands-on and interactive cooking class, a highly experienced chef will teach you step by step how to make sushi rolls from scratch. You will learn the basics of cooking and preparing the perfect sushi rice, practice knife skills to prepare the ingredients, and make a special dipping sauce. Then, of course, comes the most fun part: laying the seaweed papers and all ingredients onto the bamboo mat and rolling! Using fresh sushi-grade tuna, salmon, vegetables such as cucumber and avocado, and some secret ingredients presented by the chef, you will be surprised how easily you can recreate these recipes at home once you master the skills. It’s super easy and fun as a couple’s date night, a family activity, or as a way to spend quality time with friends!

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36-38. Go to town on these three premium dining experiences

Those surprise packages come with a little extra adrenaline than the average date and if you consider yourself an adventurous eater, we’ve got three premium dining experiences made for you and yours. This season, Fever and Wegame have cooked up a quartet of culinary experiences that include a chauffeured gastronomic journey to a mystery restaurant, a personal chef-crafted dinner in your own home, and more!

  • With Find the Dinner, you’ll be whisked away to a surprise restaurant in the city via chauffeur to then be treated to up to seven delicious dishes!
  • Bring The Dinner: A Surprise Menu at Home offers four excellent culinary experiences that range from a simple, 3-course meal to a deluxe menu that includes a premium appetizer, dish, side, and dessert, as well as a bottle of wine.
  • Find the Chef transports expert chefs to your kitchen, so that you can dine on an exquisitely crafted menu in the comfort of your own home while also learning about the details in every dish.

⭐️ Sponsored⭐️

39. Enjoy a bottomless Friday at Hubbard Inn

If fancy isn’t your thing but bang for your buck is look no further than Bottomless Fridays at Hubbard Inn. Happy hour just got a whole lot happier! Head to this trendy destination in the heart of River North for an evening of good food and drinks. Enjoy two hours of bottomless beer, house wine, and more at the patio and multi-level restaurant while devouring a delicious cheeseburger with fries. Expect contemporary dining in a great environment!

Grab your tickets here.

40. Get dinner and a (waterfront) view

Waterfront Dining Spots Chicago
Photo: @gibsonsitalia

It’s safe to say Chicago’s falls are short and sweet. They grace the city in color but they come and go all too fast. This means there’s only a limited time to enjoy the pleasant weather before the Midwest’s unforgiving winter shows its face. October usually offers up some magical nights by the water. Though we may be miles away from the ocean, that doesn’t mean we can’t still enjoy some top-notch waterfront views. From bohemian hideouts by the river to beachy hangouts by the lake, these 10 stunning waterfront spots are all currently open for outdoor dining and waiting to be enjoyed!

41-42. Take to the water

Photo: courtesy of Hornblower Cruises and Events

If the talk of water has you craving more than a dinner at the riverfront or lakefront you can hop onboard one of the many cruises taking place this fall. From Architectural River Cruises to Masquerade-themed Yacht Parties, there are so many reasons to take to the water.

43. Escape to this Tulum-inspired oasis

Once the weather does take a turn for the worse, you can still rake in the beach vibes like you’re on holiday at Diver at the Park’s new beachy escape in Wrigleyville. With tropical décor and a menu of tacos, quesadillas, and margaritas, Diver at the Park brings the charm of Mexico’s historic port city, Tulum, to one of Chicago’s liveliest neighborhoods.

Found within Wheelhouse Hotel, a boutique baseball-themed hotel located at 3477 N Clark Street, Diver at the Park has decked out a 100-person indoor space with plant life, macramé decorations, and beachy furnishings. But the coastal calm doesn’t stop there. Stepping into a huge 200-person dog-friendly patio you’ll see rustic limestone walls, bamboo furniture, and even more leafy décor. Woven hanging chairs, hanging planters, and olive trees channel that tranquil beachy vibe whilst a central tree sculpture and murals from JC Rivera give the exciting new bar a unique identity.

44. Kick back on Chicago’s biggest patio

Talking of patios, Recess’s gigantic patio in West Loop features over 14,500 square feet of bars, food stands, and cabanas housed in shipping containers.

Already holding the title of Chicago’s largest patio, a revamp has now boosted the multi-level outdoor space offering even more space on which to kick back and relax. Extra seating has been installed in many of the shipping containers and cutting “windows” into the sides means the vibrant patio now has excellent covered seating with amazing views. There are few better places to grab a drink this fall!

45. Get lost in the world’s largest corn maze

From Chicago’s biggest patio to the world’s biggest maze, if you don’t mind heading out to Richardson Adventure Farm in the north of Illinois you’re in for a guaranteed good time. When it comes to autumnal activities the Midwest has some of the best in the country. When it comes to corn mazes in particular, however, we have some of the best in the world and Richardson Farm in Spring Grove, Illinois, is a testament to that.

Holding that title of the world’s largest corn maze, the farm’s 28-acre corn maze opened to the public last month. Featuring 9-10 miles of trails, Richardson Farm’s corn maze is in fact composed of 4 smaller mini mazes weaved together by 9-10 miles of meandering walking trails. Within you’ll find a piece of all 4 seasons: tulips, sunflowers, Christmas trees, and an adventure farm. It’s a wonderful day out for those who love the thrill of getting lost in a field and trying to find their way out. 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 to pop your head up over the hedge and coordinate your path as you see fit as well as perimeter paths allowing for easy exit.

46. Howl at the Hunter’s Moon

The Hunter’s Moon is the name for the full moon following the Harvest Moon which took to the skies in September. This year October’s Hunter’s Moon will rise on October 20. According to the Farmer’s Almanac, “The Hunter’s Moon will reach peak illumination at 09:57 A.M. Chicago time on Wednesday, October 20.”

You can check out the exact time of moonrise and moonset in your location here.

47. Catch a glimpse of the Orionids Meteor Shower

From October 2 until November 7 another celestial spectacle will be taking to the skies above.  The Orionids Meteor Shower, what NASA deems “the most beautiful showers of the year”, happens each time Comet Halley returns to the inner solar system and its nucleus sheds ice and rocky dust into space. The meteors’ ‘dusty trails’ cause bright, colorful streaks in the sky throughout the month but will peak in the early morning of Thursday, October 21 when viewers are expected to witness up to 20 meteors per hour. Of course, the best viewing conditions are “well away from city or street lights”.

48. Enjoy a Sunday afternoon watching football

What better way to catch the NFL game of the night than with beers and wings! Make every Sunday NFL Sundays down at The Dime. Enjoy delicious wings, a bucket of beer, and great times with a group of friends. Booths will be prioritized for larger parties (6+) and hightops are for parties of 4. A live DJ will be there to also keep the vibes in check. There are also Thursday Night Football events at The Dime throughout October for those not free on weekends. Don’t miss out!

Get your tickets for Thursday Night Football at The Dime here and Sunday Football at The Dime here.

49. Catch a showing of Art On TheMART

Maybe football isn’t your thing and watching live visual art instead, is. Merchandise Mart’s Art on theMART has fired up all 34 digital projectors for an incredible autumn schedule featuring brand-new projections on the 25-story-tall face of the Merchandise Mart. The summer program of contemporary artwork and shows inspired by exhibitions The Obama Portraits and Frida Kahlo: Timeless has now made way for work by conceptual artist Barbara Kruger. “Untitled (Questions) 1990/2021” will run from September 17 until November 25 and will debut alongside the Art Institute of Chicago’s presentation of Thinking of You. I Mean Me. I Mean You., an in-depth look at four decades of Kruger’s practice.

The 30-minute shows will run nightly all through summer. You can read the full article here.

50. Kayak down Chicago River

Image provided by Urban Kayaks

A truly unique evening can be had combining kayaking with the Art on theMART projections. The Riverwalk and Lakefront kayaking locations are both still open and offer an astounding way to experience Chicago. Whether you’re down by Chicago Riverwalk flanked either side by the city’s famous highrise architecture or taking in the skyline from the protected waters of Monroe Harbour, kayaking in Chicago is a truly unforgettable activity and will close in the coming weeks once winter hits.

51. Enjoy the adult playground at Kanya Lounge

Another fantastic activity for adventurers thrill-seekers in Chicago can be found down at Kanya Lounge’s exclusive 2-story adult playground. Five Axe Throwing Lanes allow you to test your inner lumberjack and blow off some steam while a Rage Room Experience offers 3 unique custom-made rage rooms providing the ultimate stress reliever after the torrid months we’ve had. Either way, signature cocktails and a bucket of beers can be enjoyed in the bar and lounge area while you’re at it.

52. Hit up the largest outdoor adventure park in America

Photo: @theforgelemont

For even more taste of the action, this fall take a short drive down to Lemont, where The Forge: Lemont Quarries offer 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 the full article here.

53. Try an indoor skydiving experience

For real thrill-seekers, you might be interested in taking it a step further and testing your skydiving skills in one of Chicago’s state-of-the-art indoor skydiving centers. With an iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, there are two conveniently located cutting-edge centers to choose from. Kids and adults can both experience the same sensation you’d get 12,000 feet up in the sky and if you feel you have what it takes, you can test your vertigo above Chicago’s iconic skyline at Skydive Chicago, one of the world’s largest skydiving resorts.

54. Check out The Willis Tower’s revamped Skydeck

Image from Instagram / @mmeyers76

If vertigo-inducing experiences are your thing, high up Sears Tower, more formally known as the Willis Tower, a glass ledge breaches the building’s dimensions and stands 4ft outside of the walls of the 103rd floor. Looking down you’ll see a 1,353 ft drop staring back up at you as you sit in a tiny glass box protruding outside of what was once the world’s tallest building.

After undergoing a multimillion-dollar renovation the iconic experience recently reopened boasting even more reason to head up to the 103rd floor of the Willis Tower. The 45,000-square-foot space is now, according to the Skydeck general manager Randy Stancik, “part Chicago museum, part selfie museum, part architectural river tour, and part children’s museum.” Acting as the entrance to the Skydeck, an interactive museum featuring lighting, sounds, and visuals now offers a journey through Chicago’s history on the level below the observation deck. Many Chicagoans will be fully aware of the Skydeck but now with the exciting new features, it’s the perfect excuse to go and pay another visit.

55. Drink prosecco with 360 Views

Another superb experience up among Chicago’s sensational skyline can be had at the 360 Chicago. You can now savor a half bottle of bubbly as you take in the spectacular views of the city at the John Hancock Observatory 1,000 feet (304 meters) above the Magnificent Mile. Upgrade to the TILT option to access the brand new attraction of outward tilting glass 1,000 feet above the Magnificent Mile.

Admission for 2 with a bottle of prosecco starts at $70.

56. Savor live music & drinks at The Sanctuary

Another exciting new venue has opened in Chicago offering a new experience on the artsy edge of the West Loop. The Sanctuary is a brand-new arts and entertainment venue built inside a quaint, romantic 1885 Landmark. With vaulted ceilings, stained glass windows, vintage chandeliers, and a built-in stage, The Sanctuary offers an idyllic place to unwind after work with live music and drinks deals.

Tickets with drinks for 2 start at $75.

57. Spend the night in an enchanting tree house

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

There are plenty of people among us who like the idea of camping, but when it comes to the nitty gritty-ness of the outdoors — they bug out. No shame in that; mosquitos aren’t compliant, flat ground isn’t all that comfortable for your back, and the lack of A/C in the summer can be a real deal-breaker. Nestled in the Village of Schaumberg, the eco-friendly treehouse Air B&B is equipped with a/c for a nice room-temperature slumber. It’s also heated in the winter, but if you want to get the full experience you can do yourself one better by nestling up by its fireplace. Comforts certainly not an issue either, the treehouse is furnished with a full-sized bed and twin sleeping loft, and *checks notes* a fireman’s pole?

For further relaxation, zen out by a beautiful koi pond or inside their cedar hot tub at the foot of a waterfall.

58. Celebrate the birthday of the Chicago Theatre!

The iconic Chicago Theatre turns 100 later this month. Whether it’s catching a showing or snapping a photo outside, pay homage to one of the Windy City’s most famous landmarks this month for its centennial birthday.

59. Check-off some Chicago bucket list experiences

With Chicago back to normal and the events of the last year teaching us to never take life for granted, it’s not a fall to hold back. While we wait for international travel to return to the smooth process it once was, we should check off those bucket-list experiences close to home. As well as embracing the city’s most adored spots once again this autumn is one to fill with memorable once-in-a-lifetime type experiences. We don’t just mean bungee jumping, swimming with dolphins, and the usual bucket list experiences, but all manner of memorable activities in Chicago for both locals and tourists alike. Some of them have been mentioned above, but you can check our condensed and refinedChicago bucket list here.

60. Look into light shows

Morton Arboretum Illuminations 2015

Ok granted, the last recommendation isn’t strictly for October, but we heavily advise you get booking tickets to Light shows coming up in November. Chicago has some of the best but many of them sell out fast! Morton Arboretum, Chicago Botanic Gardens, 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 tickets go on sale and we recommend snapping them up quickly!

[Featured Image from Unsplash]

See also: 25 Must-See Street Art Murals That Prove Chicago’s Art Scene Is Legendary

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