50 Spectacular Things To Do In Chicago In September

Elliot McGowan Elliot McGowan

50 Spectacular Things To Do In Chicago In September

Make it a September to Remember.

September is here and the summer’s 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 eclectic array of museum exhibits. 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. Check out Chicago’s Chicken Rumble Soul Food Festival

The most soulful festival is making its way to Rancho 57! Don’t miss the Chicken Rumble Soul Food Festival this September 18 with Chicago’s best soul food restaurants all in one place. There will be plenty of your favorite cocktails on offer to quench your thirst, including fishbowls, long island, Hennessy margaritas, and many more! You can expect mechanical bulls, bounce houses, and the city’s hottest DJs mixing hip hop, R&B, house, and steppers. It’s guaranteed to be an unforgettable afternoon out!

You can grab tickets here.

2. Lose yourself to immersive art at the WNDR Museum

West Loop’s WNDR museum is home to a 10,000-square-foot space filled with interactive artworks by cutting-edge artists, collectives, technologists, designers, and innovators. This isn’t a museum reserved for art lovers, it’s an eclectic mix of everything. WNDR disrupts and redefines the traditional museum experience by inviting guests to fully engage with the artworks and multi-sensory installations. In May 2021, WNDR Museum was 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.

Head to the WNDR website for tickets and more information. 

3. Embrace euphoria at Chicago’s new ARC Music Festival

We began August with one of the first festivals to return to the United States at full capacity in the shape of Chicago’s beloved Lollapalooza weekend. This month Chicago begins by gearing up for the inaugural ARC Music Festival. Taking over Union Park this Labor Day weekend, the brand new festival that will pay homage to Chicago’s house music roots and honor our city’s motley musical heritage. 

Three stages will be dedicated to international house and techno artists while one entire stage will be reserved for local Chicago artists and new talent. Swedish producer Eric Prydz will perform twice under different aliases and there will also be sets from Canadian duo Bob Moses, world-renowned Italian DJ Deborah De Luca, British duo CamelPhat, and the Australian producer FISHER amongst other acclaimed artists.

The likes of Derrick Carter, DJ Heather, Gene Farris, DJ Pierre, and Hiroko Yamamura are some of the Chicago artists set to fill the festival with locally produced magic.

Grab your tickets here!

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4. Revel in Labor Day antics

There is, of course, much more than just ARC Music Festival taking place this Labor Day weekend. If festivals aren’t your thing, you can see in Labor Day weekend onboard the House Heaven Cruise and take in Chicago’s skyline from a luxurious yacht or enjoy an unparalleled Sunday Funday with Labor Day Weekend Booze Cruise!

Check out some of our best Labor Day weekend plans here.

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5. 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 Wiltshire, 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. Some of the most popular spotting locations include between Kinzie and Madison, on E Randolph Street between N State Street and N Michigan Avenue, and of course along Washington Street from Millennium Park.

6. Catch a Candlelight Concert

While Chicagohenge provides an unmissable one-off experience, Chicago’s a sublime Candlelight Concert series offers breathtaking spectacles throughout the month. Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres and some of Chicago’s most unique indoor and outdoor venues. From Latin & Tango candlelit concerts to Magical Movie Soundtrack concerts, there really is something for everybody.

A few of our favourite concerts taking place this month are:

7. 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.

8. Book a Sleepy Hollow Halloween experience

Of course, Halloween is drawing ever close which means spooky and spine-tingling events have started to announce themselves. Some of the best experiences book up instantly so why not nail down an unforgettable Halloween plan for this year?

Sleepy Hollow Bar: An Immersive Cocktail Experience begins in the middle of September and tickets are now out so you can secure a spot at this extraordinary experience! Enjoy a selection of gothic cocktails served by doting peasants, bartenders, and hosts who want to provide you with a truly magical experience based on the world of the Headless Horseman.

Get your tickets here.

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

Another unmissable Halloween plan comes in the form of the popular Dining in the Dark experience. You would think that these mysterious experiences sufficiently swindled your senses dining in total darkness but now the popular experience is receiving an ominous overhaul for the return of its Haunted Dining in the Dark season.

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.

Get your tickets here.

10-11. Kick back with goats and beer

If Dining in the Dark with the Secret Society is the pinnacle of gastronomic experiences, Brews n ‘Baahhs’ is the pinnacle of wholesome afternoons. We’ve been through a lot the past year and 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.

Brews n ‘Baahhs’ invites you to escape to the idyllic setting of GlennArt Farm for an hour hanging out with their playful and adorable goats before doubling down on those warm fuzzy feelings with a flight of craft beers on the rooftop of One Lake Brewing. This could just be the GOAT when it comes to relaxing experiences so get your tickets now.

In addition to the Brews n ‘Baahhs’: Goat Visit + Craft Beer Tasting Experience there is also a Bahmaste: BYOB Goat Yoga session taking place on September 5!

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12. Take a plunge beneath the waves at the Little Mermaid-Themed Cocktail Bar

If you’re more of an aquatic animal lover, an underwater wonderland awaits at Little Mermaid Cocktail Experience. There’s no better time to take a plunge beneath the waves, leaving the city streets in your wake, and enter the submersive theatrical Little Mermaid cocktail experience this summer.

Three bespoke nautical cocktails await you at every Little Mermaid cocktail extravaganza but secure a spot soon as only a few weeks remain and tickets are selling out fast!

Grab your tickets here.

13. See a Drunk Shakespeare show

Image taken before indoor COVID-19 measures were implemented

Another whale of a time can be found at these hilarious Drunk Shakespeare shows. This magical stage where great things happen is set in a hidden speakeasy located behind the Chicago Theater. Guests enter to 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 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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14. Attend an AirOtic Soireé Cabaret Dinner Show

Buckle up and prepare for a “Joy” ride at Chicago’s very own Joy District in River North! Join the cast of world-class acrobats every weekend for a sexy and sensual burlesque circus-style cabaret and dinner show! “AirOtic Soirée” has taken over South Florida, and has now extended shows in the Windy City through November 27!

Prepare for a night of immersive entertainment, sharing a story of love, passion, sexuality and eroticism! Extravagant costumes, seductive choreography, Adonis physiques, unbelievable stunts, and circus artistry are sure to leave you on the edge of your seat begging for more! But wait there is more…after the performance enjoy decadent cocktails and meet the performers from the show!

Don’t miss out on what is guaranteed to be a night to remember by grabbing tickets here.

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15. Let Blue Man Group blow your mind

Photo credit: Lindsey Best

When it comes to 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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16. Peruse Chicago’s legendary array of street art

Image from Unsplash

If kaleidoscopic shows of color are your thing you need not look further than the streets of Chicago themselves. Stepping outside into Chicago’s streets you can find vibrant art on every corner. Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for equality, celebrate different heritages, and honor the heroes of society. Some of Chicago’s murals are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now as much part of the Windy City’s identity as its iconic sculptures and landmarks.

If you’re not familiar with Chicago’s art scene and would like to learn about its history and the inspiration behind some of its famous murals you can head to our Must-See Chicago Murals article or jump on a West Town Street Art Walking Tour of Chicago’s famed mile-long street art corridor known as the B_Line.

You can grab tickets to an art walking tour here.

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

Perusing the many marvelous street art murals in the Windy City might just have 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.

18-21. Don’t miss the museum exhibitions closing this month

With the end of summer comes the end of several extraordinary exhibitions taking place in Chicago. We’re treated to a wonderful array of exhibitions at our many museums regularly but this year we have been spoiled. Here are some that will finish up for good in the coming weeks.

22. Dive into the world of Vincent Van Gogh at the interactive Van Gogh For All

One Van Gogh experience may be leaving the Windy City, but another arrives. The globetrotting Van Gogh for All exhibit has landed in Chicago and will be running at  333 North Michigan Avenue through September 26.

Focusing on the artist’s work from his time in Arles, Saint-Rémy, and Auvers sur Oise, the new exhibit allows guests the chance to walk in the footsteps of Vincent van Gogh and immerse themselves in his life story. Guests will find themselves in Vincent Van Gogh’s Bedroom in Arles, sat at a table from his famous Café Terrace at Night, or taking a nap with the muses of The Siesta. Visitors can be more than just passive spectators, instead, they can transport themselves directly into the world of Vincent Van Gogh and submerge themselves in the elegance of his renowned creativity.

More information and tickets can be found here.

23. Check out Chicago’s Womanish Experience

Step into a 5-story experience in the heart of Chicago. Your journey starts by walking through a 1950’s diner and invites you to explore Rhe Womanish Experience through different perspectives. Wind your way up the spiral staircase or float upon the escalator as you visit exhibits by globally known artists, statements about womanhood, and artistic explorations. Flirt with censorship in a juicy way and follow paper planes to a holographic dimension. The Womanish Experience is like nothing you’ve seen before and another wonderfully unique thing to do here in Chicago this month.

Book your tickets to this one-of-a-kind experience here.


24. Lose yourself to Marvelmania

If you’re keen to lose yourself to Marvelmania and snag a selfie with a real-life superhero, there is nowhere better on Earth right now to do that than at The World’s Largest Interactive Super Marvel Exhibit.

Open through September 6, 2021, the Museum of Science + Industry’s Marvel: Universe of Super Heroes exhibition celebrates Marvel history with more than 300 artifacts. Original comic book pages, sculptures, and a whole load of fantastic interactive displays offer a day of unparalleled Marvel fun. 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.

25. Visit the Field Museum of Natural History for free

Every Wednesday of September, starting September 1, Illinois residents can enter the popular natural history museum completely free. According to the Field Museum website, “tickets for Free Days are only available to Illinois residents onsite and cannot be reserved in advance. Please ask a Guest Relations staff member when you arrive at the museum and be ready to show your Illinois proof of residency.”

In addition to an Illinois identification card, Field museum has stated that the following are also accepted as valid ID: Illinois lease, Illinois library card, Illinois student ID with photo, Illinois utility bill, Illinois work ID, and Illinois driver’s licenses.

Read the full article here.

26. 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.

27. 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, 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:

  • Garden Of The Gods: Saline County
  • Cave-In-Rock: Hardin County
  • Wildcat Canyon In Starved Rock State Park: La Salle County
  • Cache River State Natural Area: Johnson 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

28. Go Apple Picking

Photo credit: @shayna.friedman

While we’ll miss the blooming gardens and sunflower fields of summer but we’re also excited for the changing leaves, pumpkin patches, and orchards to harvest the fruits of fall. The peak season to apple pick starts rolling from 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.

29. 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.

30. 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.

31-34. Go to town on these four 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 four 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.
  • Let date night go all night with the Find the Room experience! This luxury experience lets diners go all out with a luxury night away in a three, four, or five-star hotel room complete with a surprise extravagant dinner.

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35. 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

36. Max out on the end of summer vibes at Wrigleyville’s new Tulum-themed patio

A new Mexican restaurant has opened a stone’s throw from Wrigley Field offering Cubs fans an idyllic beach-like escape. 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 on N Clark Street, Diver at the Park has decked out a 100-person indoor space with plant life and macramé decorations. Stepping into a huge 200-person dog-friendly patio, however, you’ll be welcomed with tranquil beachy vibes.  Rustic limestone walls, bamboo furniture, woven hanging chairs, and more leafy décor create the Tulum vibes while murals from JC Rivera give the bar a unique identity.

You can read the full article here.

37. Kick back on Chicago’s biggest patio

Photo: @chicagoinrecess

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 summer!

38. Get dinner and a (waterfront) view

patios Chicago
Photo from Instagram / @beatnikontheriver

We may be miles away from the ocean but 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!

39. Head out to the thriving Village Of Rosemont

With all that Chicago has to offer, those of us who live near the epicenter of our wonderful metropolis can sometimes be found guilty of turning a blind eye to what lies further afield. While patios offer an escape of sorts, the Village of Rosemont offers a wonderful break from the city clamor.

Home to the only two-level indoor outlet shopping center in the Midwest with over 130 designer stores as well as the vibrant Parkway Bank Park entertainment district there is so much to do. Free concerts, 40 amazing restaurants, 17 luxury hotels, and a jam-packed event calendar ensure that there is something for everybody.

Check out what’s going in Rosemont here.

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40. Catch a showing of Art On The MART

Back in the Windy City, Merchandise Mart’s Art on the MART fired up all 34 digital projectors for an incredible summer schedule featuring brand-new projections on the 25-story-tall face of the Merchandise Mart. The Obama Portraits, projections inspired by the Frida Kahlo: Timeless exhibition, and shows Footnotes, Woven, and the light of the dark are all currently showing every night through September 16.

The next projections will be “Untitled (Questions) 1990/2021″ by the legendary contemporary artist Barbara Kruger and will run from September 17 until November 25. They 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.

41. 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 have been open through summer 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.

42. Relax and reset with a day of river tubing

If an aquatic adventure sounds up your street but you’re looking for a little breather and an escape from our urban jungle but not for a long time, Sourced Adventures has the answer. River Tubing & Brewery Day Trips on the Tippecanoe River offer the perfect daybreak. After getting picked up from central Chicago you’ll be whisked away to a stunning section of the 182-mile-long Tippecanoe River. There you’ll pick up your included tube rental, pack cooler floats with your chosen beverages, and blissfully bob your worries away.

You can grab tickets for River Tubing and Brewery Day Trips here

43. 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.

44. Play Whirlyball

For those who aren’t tempted by axes and rage rooms, Whirlyball might be the activity for you. If ESPN The Ocho were a real channel, chances are you could catch Whirlyball on there, probably on weekend nights. The game involves elements of lacrosse, hockey, and basketball, as well as — you guessed it — bumper cars. Now, you’ll be able to try your hand/paddle/foot at the game with Whirlyball back open for bookings.

If that’s just not your game, the Whirlyball facility is also the home of a multi-level laser-tag arena, bowling suites, billiards (at their Vernon Hills location), and arcade games.

Head over to whirlyball.com/chicago for more information.

45. Hit up the largest outdoor adventure park in America

Photo from Instagram / @theforgelemont

For even more taste of the action, this summer 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

46. 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.

47. Check out The Willis Tower’s revamped Skydeck

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 has now 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.

48. 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.

49. Savor live music & drinks at The Sanctuary

Another new exciting venue has opened in Chicago offering an exciting 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.

50. Check-off some Chicago bucket list experiences

With Chicago returning back to normal and the events of the last year teaching us to never take life for granted, it’s not a month 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 summer is a summer 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. Many of them have been mentioned above, but you can check our condensed and refinedChicago bucket list here.

See more: 15 Fantastic Free Things To Do In Chicago

[Featured Image from Unsplash]

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