Make it a September to remember.
September is here and the summer weather is about to transition into autumn cheer. We’ve been treated to an erratic summer with sunshine and summer storms taking it in turns for a spot in the skies above.
There’s plenty taking place in Chicago right now, from enchanting candlelight concerts to an abundance of museum free days. On top of that, there are unmissable one-off events like Labor Day celebrations and the Autumn Equinox.
Here are the best things to do in Chicago this September!
1. Revel in Labor Day antics
There is loads going on for Labor Day this year and you can find plenty of options in our roundup of the most amazing things to this Labor Day weekend in Chicago. Our pick of the bunch, however, (if you’re willing to push the boat out a little with regards to expenses) has to be don’t he of the Labor Day Booze cruises taking place on Lake Michigan.
Both the Labor Day Sunday Funday Booze Cruise on Sunday at 4pm and the Labor Day Sunday Funday Sunset Cruise! at 7:30 pm offer exhilarating ways to spend Sunday.
Float down the Chicago River while enjoying a live DJ set take in breathtaking views of Chicago’s skyline as you sail out onto Lake Michigan with your friends.
Check out some Labor Day weekend recommendations here.
2. Marvel at the magical autumn Chicagohenge
Of all the events to look forward to this month, one of our favorites is certainly autumn equinox and the resulting Chicagohenge. The bi-annual event occurs for the spring and fall equinoxes. Dubbed ‘Chicagohenge’ after the famous prehistoric boulder formation in England, the astrological phenomenon sees the magic of nature and Chicago’s glorious architecture collaborate harmoniously to put on a breathtaking spectacle that people from all over come to witness.
Because Chicago was built on a grid system with streets lining up near perfectly on compass north to south and east to west, the sun lines up directly with Chicago’s east-west facing streets and beams down the heart of the city splashing through Chicago’s artificial valleys.
Find out more about where and when to best experience this fall’s Chicagohenge here.
3. Travel back to the prohibition era at The Roar Speakeasy
Go back in time to Chicago’s Prohibition Era at The Roar on Rush! A lively Speakeasy that lights the way to a hidden 4-room cocktail experience where you will meet vibrant figures from the elaborate web of a Roaring Twenties bootlegging operation. Each room tells a story and is paired with a cocktail tasting from Prohibition times! Afterwards, take a seat in the Speakeasy for more cocktails, food, and live music with special performances. Break out your best flapper dresses and linen jackets, this cocktail party at The Roar is not to be missed!
4-9. Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but this fall there are some extra special concerts taking place in extraordinary venues all over the city. Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most unique spaces with surreal acoustics. Here are some of our favorite Candlelight concerts taking place this month:
- Candlelight Open Air: From Bach to The Beatles at Artifact Events on September 11
- Candlelight: Country Classics feat. Patsy, Dolly, and Hank’s Best Hits at Salvage One on September 15
- Candlelight: A Tribute to Adeleat Stan Mansion on September 28
- Candlelight: A Tribute to Juan Gabriel at Salvage One on September 29
- Candlelight: A Tribute to Taylor Swift at Stan Mansion
See the full list of candlelight concerts taking place in Chicago here.
10-11. 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 and Immersive Live Jazz & Cocktails both ensure memorable nights of dining, drinking, and the magic of jazz in a truly vivacious venue.
Grab tickets for Immersive Live Jazz & Dinner for Two here and Immersive Live Jazz & Cocktails here.
12. Enjoy a concert under the stars
Swap the flicker of candles for the glimmer of stars at one of Chicago’s extraordinary Concerts Under The Stars series. These open-air experiences will set you back in time with an array of unique vintage sounds in beautiful star-lit venues. Experience the works of Sinatra, Ella Fitzgerald, Amy Winehouse, moving movie ballads, and more presented by Chicago’s finest while sipping a martini in a jazz-age vibe.
Our personal favorite concert, Sinatra Under the Stars, is taking place at the Hyatt Centric The Loop Hotel’s stunning Aire Rooftop bar on both Sunday, September 11, and Sunday, September 25.
Check out all concerts under the stars here.
13-15. Enjoy the ground-breaking energy of Chicago’s Body Language dance spectacles
If you’d rather sit back and admire edgy fashion and spectacular dance skills, Chicago’s Body Language Dance Performances are for you. Set in a gorgeous photoshoot atmosphere that offers all the glamour of a fashion catwalk with the cozy comfort of a sofa, dancers from the city’s very own Redd’s Angelz crew will blow you away pushing the limits of creative expression through dance.
A few of our favorite performances are:
Body Language: African Drum and Dance Performance
Body Language: Keeper of the Floor Live Dance Competition
Body Language: Indian Dance and Music Showcase
Grab tickets to a Body Language dance extravaganza here and if you’re quick using the code BODYLANGUAGE at checkout on the Fever app will bag you free tickets first-come, first-served basis.
16. Check out the interactive multisensory ‘Prince’ experience
Music lovers, casual fans, and superfans of legendary musician Prince can now rejoice in the dynamic, multisensory, first-of-its-kind immersive experience, making its worldwide debut in Chicago through January.
Superfly and The Prince Estate are collaborating to present Prince: The Immersive Experience, a multi-faceted musical universe revolving around the iconic artist, inviting guests to be completely immersed in the exhilarating, singular talent of a superstar who brought us hits like “When Doves Cry,” “Raspberry Beret,” and “Purple Rain.”
More information and tickets for Prince: The Immersive Experience can be found here.
17. Marvel at a 360° exhibition featuring the iconic art collection of the Louvre™
The Musée du Louvre™ in Paris is undeniably one of the most iconic and recognizable art museums worldwide, drawing over 7 million visitors a year to its famous rhombus-shaped glass museum.
Louvre™ Fantastique: The Exhibition arrived in Chicagoland this summer offering Chicagoans a 360° experience, showcasing over 70 reimagined masterpieces that are famously on display at the Louvre™. Closing on Sunday, September 18, this month is the last chance to experience one of Paris’ main attractions right here at our doorstep.
More information and tickets can be found here.
18-20. Explore some of Chicago’s most popular museums and attractions for free midweek
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 month Shedd Aquarium, Field Museum, AND the Museum of Science & Industry are all offering free midweek days throughout September.
More information about Field Museum’s free days can be found here.
More information about Shedd Aquarium’s free days can be found here.
More information about the Museum of Science and Industry’s free days can be found here.
21. 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.
More information and tickets can be found here or opt for a reduced entrance if you’re a senior resident, teacher, or student.
22. Gaze at the stars at the Adler Planetarium for free on a Wednesday
Yet another of Chicago’s famed attractions, The Adler Planetarium, reopened this year after a two-year hiatus. The planetarium now boasts a brand new telescope in the Doane Observatory which holds the title of the largest public telescope in the Chicago area.
As well as a new observation park, guests will notice the planetarium’s shiny new dome roof which has been restored with brand-new copper tiles giving the 80-year-old dome an iconic new glow. The best news, however, is that Illinois residents can enter for free every Wednesday evening from 4-10 pm provided they bring proof of residency.
More information and tickets can be found at adlerplanetarium.org.
23. Enjoy the “Wings Of Mexico” before it goes
One of the most wonderful things about our city is that you need not just look inside Chicago’s groundbreaking museums to be inspired by art. Chicago’s array of public art pieces is second to none and there are incredible creations all over the city. Head to our article on Chicago’s most spectacular monuments and public art pieces for a full breakdown of the most impressive and where they can be found, but whatever you do make sure you head out and admire the “Wings Of Mexico” art installation on The Magnificent Mile before it leaves at the end of the month.
24. See the last of Art on the MART’s summer showings
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.
Taking place nightly at 9:00 pm and 9:30 pm, 34 digital projectors will be displaying the summer schedule through September 7. This means it’s the last chance to see Billiken by Shkunna Stewart and Wills Glasspiegel, explore by Jonas Denzel, and Nick Cave’s Ba Boom Boom Pa Pop Pop.
25. Check out the Boozy Cauldron Tavern Cocktail Experience
The Boozy Cauldron Tavern is popping up in Chicago for a 4-part cocktail experience led by Professor Dolohov Draven and his top students. You will be taken on a magical journey where you can imbibe on the four delicious signature cocktails (including the Tavern’s Famous Butternilla Brew) and hear and feel the stories surrounding the famous tavern and the ghosts that still haunt the establishment. Be quick to head over, for the Boozy Cauldron travels the nation and only appears for a limited time in select cities; after its last day, the portal closes and the Tavern disappears!
Grab tickets here before it leaves Chicago on September 24!
26-30. Revel in the many events at the Grand Cabaret After Dark speakeasy
If you really want a buzz we suggest you head down to Porkchop’s speakeasy “Grand Cabaret After Dark” in West Loop this month for a roster of rip-roaring revelry.
On Fridays’s STRIPPED provides a decadent and debaucherous night of burlesque followed by The Grand Cockpit: Chicago’s hottest cabaret show with jaw-dropping steamy performances from Bad Boys Live.
Both action-packed shows are no-holds-barred adult fun that makes for the perfect Friday night adventure while on Saturdays you’ll find vintage evenings of cabaret, jazz, and magic at The Grand Cabaret After Dark from 6 pm followed by Peep Show Burlesque at 9 pm.
Check out all the chaos going on at Porkchop’s Grand Cabaret After Dark here!
31. See a burlesque and belly dance show at the Newport Theatre
Grand Cabaret is far from Chicago’s only speakeasy burlesque experience. Catch some of Chicago’s finest burlesque, belly dance, drag, and variety entertainers plus screenings of incredible digital content at The Newport Theatre’s Newport Peek-Easy Burlesque Show. Specialty cocktails, intimate tables, and a true speakeasy feel make this a night like no other!
More information and tickets can be found here.
32. Revel in the pandemonium of a Drunk Shakespeare show
Another brilliant experience 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.
33. Chuckle away at Chicago comedy show
We could all do with a chuckle with the tumultuous years we’ve had and luckily there’s no place better for that than at a Chicago comedy show. At Laugh Factory Chicago some of today’s biggest names and local comedians are delivering something for every taste and style throughout September.
Grab tickets to a show at Laugh Factory Chicago here.
34. Kick back with goats and beer
If live shows are a little bit too lively for you after an intense summer we’ve got just the ticket. 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 afterward, double down on those warm fuzzy feelings with a few flights of delicious craft beers on the rooftop of One Lake Brewing with this exclusive Brews n ‘Baahhs’ experience. 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.
35. Enjoy a flight of beer at the Pilot Project Tasting Room
If craft beer floats your boat another fun tasting experience this month comes in the form of a beer flight at Pilot Project Brewing. Pilot Project Brewing is a brewery incubator, tasting room & cafe located on Milwaukee Ave in Logan Square, Chicago. Pilot Project was launched as a collaborative and artistically curious space to help support talented brewers in an industry with exceptionally high barriers.
Modeled after the music industry, Pilot serves as a launchpad for start-up breweries, offering assistance with fine-tuning recipes, production, business development, marketing, distribution, and more. They are Chicago’s incubator dedicated to the art of brewing and a community inspired by the craft. Pick from 24 taps to make your perfect flight of beer and taste and compare with your besties
You can purchase a flight of beer at the Pilot Project Tasting Room here.
36. Embrace the peak of patio season at Chicago’s largest patio
Despite the end of summer on the horizon, it’s still very much patio season in Chicago. You’ll likely agree Chicago doesn’t play around when it comes to patio season. Come rain or shine, if a patio is opened somewhere in the Windy City, guaranteed Chicagoans are out there clinking drinks. We’ve rounded up the very best patios and beer gardens in and around Chicago to give you an essential range of options but if there is one that’s ideal for soaking up the last of the summer sun it has to be Recess’s gigantic patio bar.
Nestled within 30 shipping containers on a West Loop corner, Recess is home to a cozy amalgamation of bars, food stands, and cabana houses within a 14,500 -square-foot space that holds the title of the largest patio in Chicago. The stacked shipping containers give it an awesome reclaimed industrial vibe while the fusion of plant life and vibrant murals make it a brilliant summer hideout. There are few better places to grab a drink this summer!
Find our full list of Chicago’s best patios here!
37. Get lost in the ‘World’s Largest Corn Maze’
It might still technically be summer but all that fall fun is beginning to announce itself. Pumpkin patches, apple orchards, and corn mazes — some of our favorite autumnal activities — are emerging and the Midwest has some of the best in the country.
When it comes to corn mazes, however, we have some of the best in the world and Richardson Farm in Spring Grove, Illinois, is a testament to that.
Holding the title of the world’s largest corn maze, the farm’s 28-acre labyrinth will open to the public on Saturday, September 10, and this year will pay homage to none other than the world’s most famous spy.
38. Go apple picking
While we’ll miss the blooming gardens and sunflower fields of summer we’re also excited for the changing leaves and orchards to harvest the fruits of fall. The peak season for apple pick starts rolling from 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!
39. Surround yourself in sunflowers
If you’re happy to head outside of Chicago to Oglesby you’ll be treated to endless, gorgeous sunflower fields at Matthiessen State Park.
The park covers a total of 1,629 acres with over 60 dedicated exclusively to towering sunflower fields. It’s a sight to behold, filled to the brim with yellow blooms. The flowers first begin to bloom in the middle of summer and start to wilt in early September, so head on over soon for a look at the field in all its glory!
Find out more information here.
40. Head out of the city and see Illinois’ natural spectacles
If you’re one who enjoys being surrounded by nature then heading out to the quiet of Illinois’ natural beauty in September as the leaves begin to change makes for an unforgettable experience.
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, here are 7 natural wonders of Illinois that you can visit while they’re about to peak:
- Garden Of The Gods: Saline County
- Wildcat Canyon In Starved Rock State Park: La Salle County
- Cache River State Natural Area: Johnson County
- Cave-In-Rock: Hardin County
- The Pomona Natural Bridge: Jackson County
- Cascade Falls In Matthiessen State Park: La Salle County
- Bork Falls In Ferne Clyffe State Park: Johnson County
More information can be found here.
41. 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.
42. 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.
43. Watch an outdoor movie
With the weather still allowing outdoor fun to thrive, another fantastic end-of-summer plan comes in the form of catching a free outdoor movie showing at Gallagher Way in Wrigleyville on select Wednesdays through the end of September.
You can see the full Movies at Gallagher Way schedule here.
44. Kick back in an AMC movie theatre
If you’re a purist and would rather watch a movie in optimum conditions, AMC Theatres® is the place to go this month. Whether it’s a rainy afternoon or a special date night, all the best comedies, action flicks, and everything in between can be enjoyed at a discount in Chicago, and nationally, with an AMC black ticket
45-48. Savor sensational food samples on a food tour
For foodies who prefer to sample tasty delicacies over perusing extraordinary street art, there is a range of fantastic food tours for all manner of foodies.
Taste all of Chicago’s classic eats on a four-hour guided bicycle tour courtesy of America’s longest-running city bicycle tour company with Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour. The journey is 14 miles in total (traversed at a nice leisurely pace) and includes a slice of deep-dish pizza, a gourmet brownie, a Chicago-style hot dog, and a few samples of Chicago’s legendary craft beer!
Alternatively, you can sign up for the ultimate foodie adventure in Chicago’s historic River North with Lonely Planet Experiences: River North Historical Food Tour. Join a local expert and uncover hidden gems and the best spots for some of the city’s best-loved dishes. This tour will leave you filled with delicious local foods as well as some insider knowledge of the city’s culinary history and culture.
Despite having a kaleidoscopic food scene offering all manner of savory and sweet treats, nothing in Chicago has truly celebrated donuts in all their glory, until now. The Underground Donut Tour is Chicago’s first-ever donut tour and was born to give those who truly enjoy donuts the perfect excuse to sample the Windy City’s very best. Tours include such favorites as Do-Rite Donuts, Firecakes, Stans, and Doughnut Vault as well as some lesser-known spots.
Grab tickets to the Bikes, Bites, and Brews tour here.
Grab tickets to a River North Historical Food Tour here.
Grab tickets to a donut tour here.
49. Learn to make your own sushi
If touring all the wonderful cuisine has you inspired you might be interested in acquiring a new culinary skill. Learning to make sushi from the comfort of your own home is another fulfilling activity you can do this month. 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 family activity, couple’s date night, or as a way to spend quality time with friends!
Grab tickets to a sushi-making class here.
50. Head up to London House’s inaugural “Luminescence” experience
London House Chicago, a luxury hotel known for its unmatched sweeping views of the Magnificent Mile and the Chicago River, this summer launched an inaugural illuminated experience up on its award-winning rooftop.
Located on the famed 22nd-floor terrace at 85 East Wacker Drive, “Luminescence” offers guests an illuminated botanical urban paradise up in the sky. A vibrant array of multi-colored, floral-themed LED lights sprawl across walls and hang over the iconic rooftop giving it a never-before-seen look.
With colder weather looming it is the perfect place to make some late summer memories up on one of Chicago’s most marvelous rooftops.
More information can be found here.
51. Kayak down the Chicago river
Another unforgettable activity can be enjoyed courtesy of Urban Kayaks. Kayaks and paddleboards can be rented from various operators at both Monroe Harbor and Chicago Riverwalk locations but it is the river where the most unique experience can be found.
Flanked on either side by Chicago’s famous highrise architecture, you can venture through the city’s heart via skyscraper canyons and under historic bridges. An evening kayak makes for a truly memorable night navigating the waters while the sun sets and the hustle and bustle of the riverwalk activity takes off around you.
The kayaking season operates as the weather allows which means this month is one of the last chances you’ll get for a while!
52. Try an indoor skydiving experience
If you’re the outdoorsy type who likes a thrill you’re probably the type who would be interested in 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.
53. 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 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!
54. See the world’s largest display of LEGO art in Chicago
Another superlative claim, but this time it’s about that magnificent invention that has captured the imagination of children and adults for years. One of the most bizarre yet brilliant exhibitions we’ve seen in a while is currently taking place at Chicago’s Museum of Science and Industry and it has just been extended through January 2023 giving you more time to experience it if you haven’t done so already!
‘The Art of the Brick’ features more than one million LEGO bricks transformed into more than 100 sculptures by award-winning artist Nathan Sawaya. You’ll walk through recreations of famous masterpieces like Van Gogh’s ‘Starry Night’, Da Vinci’s ‘Mona Lisa’, and Grant Wood’s ‘American Gothic’, as well as a sculpture of a 20-foot-long Tyrannosaurus Rex skeleton.
55. Grab tickets to Chicago’s incoming Harry Potter experience
Potterheads, prepare for a first-of-its-kind Harry Potter™ interactive experience that will inspire your inner wizard coming to Chicago this November!
Wizards of all ages will be enthralled with this hands-on adventure. There will be plenty of magical moments to enjoy in a massive 30,000-square-foot space when Harry Potter™: Magic at Play unveils at the Water Tower Place at 835 Michigan Ave, Chicago, IL 60611, at the corner of North Michigan Avenue and East Pearson Street.
[Featured Image from Unsplash]