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30 Marvelous Things To Do In Chicago In May

By Elliot McGowan

30 Marvelous Things To Do In Chicago In May

We’re in the heart of spring and summer is just around the corner!

The light at the end of the tunnel is drawing nearer by the day. May has been marked by optimism thanks to news that the city could return to normal in July and many annual events and festivities will go ahead in August. As spring weather shines on Chicago and the vaccine roll-out is accelerating our favorite activities and establishments are making a comeback.

Navy Pier has reopened with weekly firework shows through May, kayaking has returned to the river, restrictions are set to be loosened even further granting indoor and outdoor gatherings more freedom, and a number of unique events have either resumed or have arrived in Chicago for the first time. From kayaking past the new Art on the MART show to looking to the skies for a blood-red lunar eclipse later in the month here are our top recommendations for the best things to do in Chicago this May.

1. Check Out Artopia: Chicago’s Immersive Art Experience


Opened in April, Artopia is offering guests a multi-dimensional, hands-free journey utilizing digital displays and interactive technology that make it as safe as it is mind-blowing. Sound-reactive LEDs, large-scale light art, holographic fan technology, and interactive projection mapping provide futuristic synergy whilst 8 large-scale sculptures and 20 murals harmonize the authentic with the avant-garde.

Tickets start at just $30 for the one-hour-long journey through Artopia while VIP Access Tickets come with a specialty cocktail in The Artopia Lounge afterward and ICON Access tickets offer entry, a specialty cocktail, and an exclusive Artopia T-shirt.

Artopia After Dark: Burlesque, Cocktails & More offer the chance to experience special cabaret-style shows, burlesque performances, and live DJs in Artopia Lounge’s cabaret setting.  This weekend May 8-9 there will also be two one-off events taking place within the 32,000 square ft exhibit. BAM & Rituals Presents: Artopia After Dark is an exclusive late-night experience of Artopia taking place Saturday night, May 8, while Artopia Liquid Drag Brunch offers the ideal Sunday Funday activity this Sunday, May 9.

2. Experience The Sistine Chapel Up Close And Personal

Another unmissable event is Michelangelo’s Sistine Chapel: The Exhibit. Imagine having the chance to stop and admire the stunning frescos the famous Italian artist painted across the historical Sistine Chapel. Imagine being able to do so without the price point of a flight to Italy.

That’s exactly what you’ll do at Michelangelo’s Sistine Chapel: The Exhibit coming to Chicago on May 19! This amazing event showcases the awe and wonder of arguably one of mankind’s greatest artistic achievements while allowing its visitors to experience this art from an Up-Close, Life-Sized, and Never-Before-Seen perspective. And tickets for this unique exhibit have just been released to the public!.

3. Unleash Your Creativity At An Urban Art Workshop

After seeing so much mind-blowing art at one of the aforementioned events you may just be inspired to give a go at creating something yourself. At Chicago’s Spray Paint ‘n’ Sip Urban Art Workshops guests are invited to unleash their inner street artist on a personal 50ft mural.

Running every week Fridays through Sundays, tickets to these BYOB Urban Art Workshops grant attendees access to a 90ft x 30ft heavy-ventilated indoor studio with 50ft of wall space to create a mural of their own under the guidance of a private instructor while sipping away on whatever tipple you prefer.

If you’re wanting more inspiration, you can of course peruse the many must-see street art murals of Chicago to fuel your imagination.

4. Dine In Darkness With The Secret Society

One exclusive experience we’ve had on our radar for some months has now taken up residence in River North. Dinining in the Dark with The Secret Society is taking place several days a week through July and with tickets selling fast it is time to secure a spot at this confidential culinary experience.

There a masked and mysterious amalgamation of characters will welcome you to your table before the room suddenly becomes shrouded in darkness. An eerie atmosphere encircles you but the ensemble of enigmatic assistants will serve you pleasantly as you dabble between mouth-watering dishes and several trivial tests and trials accompany the evening.

This is far from the mundane dining experience you’re used to. Eminent psychologists have been advocating dining in the dark as the ultimate gastronomic experience for years but at this Dinining in the Dark with The Secret Society a fusion of exceptional dishes and eerie enigma offer a night you won’t forget.

5. 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 your choice 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.

6. Be Blown Away By A Candlelight Concert

Few things can better the spectacle provided by Fever Original’s sublime Candlelight Concerts. Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most stunning venues. With open-air concerts starting to open with the improving weather and loosening restrictions you can now listen to musical masterpieces as sunlight fades to candlelight.

There are a wide range of indoor Candlelight concerts and open-air Candlelight concerts to choose from with various genres from classical and jazz greats to Disney and anime movie soundtracks. Here are some of our top picks:

7. Savor Live Music & Drinks In The Sanctuary

Despite the prowess of Candlelight concerts, they are of course, far from the only live music currently happening in Chicago. The Sanctuary is one of three live concert venues at the brand-new arts and entertainment venue located on the artsy edge of the West Loop.

The quaint, romantic 1885 Landmark features vaulted ceilings, stained glass windows, vintage chandeliers, and a built-in stage complemented by a private Niche Bar and Lounge offering an idyllic place to unwind after work with live music and drinks deals. Tickets with drinks for 2 start at $75.

8. Enjoy Intimate Live Jazz At Le Piano

There are plenty of wonderful places to see live jazz in its rawest form here in Chicago. Le Piano, however, offers one of the most intimate and romantic experiences.

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, drinks, and intimate performances. Exclusive packages offer deals such as Immersive Live Jazz & Dinner for Two or Immersive Live Jazz & Cocktails. Dine and drink as live music softly resonate around you in this cozy, romantic, and magical venue.

9. Marvel At Magic & Music At Chicago’s Newest Speakeasy

Talking of magic, with the return of live performances, it’s not just music on the cards. If you head down to West Loop’s Grand Cabaret After Dark this month you’ll find a vintage evening of jazz and magic in Chicago’s newest speakeasy. Featuring live jazz music of classics and contemporary songs by the E-Line Organ Trio, and some mysterious magic by Mr. Jim Bergstrom! A delectable dinner and BYOB drinks rules ensure an all-round night of mystery and marvel.

10. Embrace Spring At River North’s Secret Garden Pop-Up

Another astounding venue offering an exceptional springtime experience is River North’s Hubbard Inn. In the celestial leafy lounge setup of Blue Violet, on the second floor of Hubbard Inn, the cocktail bar has combined cascading greenery and a stylish interior where mouth-watering bottomless mimosa brunches are now taking place until the end of June.

There are few places offering a Sunday Funday as good as the one found down at The Secret Garden Spring Pop-Up but if you can’t bask in the seasonal bloom on the weekend, worry not. The sweet selection of spring-themed cocktails can also be enjoyed during Floral Happy Hour between 5 pm and 7 pm Wednesdays, Thursdays, and Fridays until June 24th.

Floral Cocktails and Happy Hour tickets start at $25 for entry, discounts on a range of signature cocktails with floral themes and custom glassware as well as an array of Instagrammable moments.

11. Brunch Harder At the Dime

Nothing puts a spring in your step like a good brunch and the Secret Garden Spring Pop-Up isn’t the only solid brunch around. Another great brunch setup can be found at The Dime. Bottomless Brunch with Mimosas, Bellinis & More are happening every weekend for the whole of summer. Great music, food, and drinks make The Dime another brilliant place to brunch with your quarantine crew. Tickets include bottomless mimosas, bellinis, beers, and one entree from The Dime’s brunch menu.

12. Chuckle Away At Laugh Factory Chicago

Live performances are making a gradual return which means standup comedy has returned to Laugh Factory Chicago. Some of today’s biggest names and local comedians are delivering something for every taste and style throughout May. Every safety precaution has been taken to make sure you can enjoy live comedy safely and with the hysterical skits on offer, nights at Laugh Factory Chicago will have you forgetting all about the trials and tribulations of the last year. General Admission to Laugh Factory Chicago for 1 person is $20.

13. Check Out The Magic Selfies Museum

Somewhere else you are guaranteed a good laugh is at Chicago’s new Magic Selfies: An Immersive Selfie Installation. With over 10 magic curated rooms and over 20 walls of all different shapes and layouts the Magic Selfies Museum is Chicago’s very own selfie playground created to offer the absolute perfect conditions for taking unique and iconic photos.

The exclusive range of fun photo ops has been meticulously curated just for the ‘Gram with everything from artsy color-coordinated recreations to polychromatic backdrops. Ride atop a unicorn or recline in a toy duck-infested bath, a plethora of photo-friendly setups are waiting for $25 per person!

14. Lose Yourself To Marvelmania 

Maybe instead you’d rather snag a selfie with a real-life superhero. If that is the case 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.

15. Step Inside The Mind Of Van Gogh

Another exhibition open through September that shouldn’t be missed is Lighthouse Artspace Chicago: Immersive Van Gogh Exhibit. The 35-foot walls of the Victorian landmark’s Lighthouse ArtSpace Chicago are now adorned with flawless digital projections that offer an art experience like no other.

Surrounded by famous works like IrisesThe Bedroom in Arles, and Starry Night, guests can take an hour-long journey through the kaleidoscopic displays and submerge themselves in the elegance of Van Gogh’s creativity whilst unraveling his tormented mind. Designed and conceived by Massimiliano Siccardi and Luca Longobardi, who pioneered the exhibition’s Parisian precursor, guests are invited to “step inside” Van Gogh’s iconic creations and walk through the memories of the eccentric genius experiencing the passion behind every laden brushstroke.

16. Immerse Yourself In The Life Of Nelson Mandela

Nelson Mandela addresses South Africans for the first time after his release from prison, from the balcony of the City Hall on the Grand Parade, Cape Town.

From an exhibition exploring the ingenuity of one of history’s most famous painters to an exhibition that pays homage to one of the 20th century’s most iconic figures. Mandela: Struggle for Freedom honors the eponymous human rights champion, his legacy, and his unbreakable will while also exploring themes such as “the role of nonviolent protest, the power of youth, and the indignities of incarceration that still resonate today.”

The exhibit is comprised of five different zones named: Apartheid, Defiance, Repression, Mobilization, and Freedom. These tell the story of the fight against apartheid using imagery, soundscape, digital media, and artifacts.

Among its many dramatic features, the immersive exhibition has a replica of the eight-foot by seven-foot cell where the Nobel Peace Prize winner spent 18 years of his life and a room where an enormous tank-like truck emerges from one wall moving towards the onlookers. Visitors who dare can grab a trash-can lid as their only protection and get a feel of what it was like to be a student during the Soweto uprising.

17. Keep An Eye Out For Human+Nature At Morton Arboretum

Photo Credit: Phoebe Montague.

An exhibition that explores another contemporary issue is Morton Arboretum’s “Human+Nature”. The arbor-inspired exhibition will feature five 20-25-foot art installations from the internationally renowned South African artist, Daniel Popper. The massive natural sculptures will tower over various locations across the 1,700-acre tree museum and research center, leading guests to areas they may not have explored before.

Previously planned to open on April 9, 2021, some exhibition materials remain in transit to the Arboretum due to pandemic-related shipping delays, and consequently, a new exhibition opening date will be released soon. The new opening date is expected in May so keep your eyes open for when it might be!

18. Kayak Down Chicago River

Image provided by Urban Kayaks

Something that has returned on time is Chicago’s iconic kayaking experiences. 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. After shutting down for the winter season, kayaking made a return to Chicago at the beginning of May.

The Riverwalk and Lakefront locations opened for their spring and summer seasons on Saturday, May 1, whilst Lake Michigan kayaking and paddleboarding will open on May 21.

19. See The Spring Schedule Of Art on the MART

Art on the MART returned last month and fired up all 34 digital projectors for a Spring 2021 Program in collaboration with Adler Planetarium. The 25-story-tall face of the Merchandise Mart is now showing the world premiere of ‘Astrographics’ which will “explore ways in which humans conceptualize and visualize their universe, and how that has changed over time.”

Produced by the Adler Planetarium, the scientific visualizations are based on real data showing the scale of the universe and “will transport the viewer from Earth to other planets and stars, then out to deeper and more speculative realms.” A truly unique evening could combine kayaking with the 30-minute shows that run nightly at 8:30 pm and 9:00 pm.

20. Catch A Navy Pier Firework Show

Another fantastic visual experience can be enjoyed every Saturday at 9 pm. The Navy Pier finally reopened at the end of April after its longest closure in recent history and launched its first firework show of 2021 on May 1. As part of the Pier’s phased reopening 10-minute fireworks shows will light up the skies every Saturday night at 9 pm through May with the last show set to take place on Memorial Day weekend at 9 pm on Saturday, May 29.

21. Drink Prosecco With 360 Views

With the sun beginning to shine, there is no better time to head up to 360 Chicago and take in the unparalleled views of our sensational skyline. You can now savor a half bottle of bubbly as you take in the spectacular views of the city 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. Time it right and you might even be able to catch a firework show in May!

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

22. Check Out The Willis Tower’s Revamped Skydeck

Another vertigo-inducing experience is found over at the tallest tower in Chicago (and the third tallest in the United States. 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.

23. Try An Indoor Skydiving Experience

If you’re an adrenaline junkie and the height hasn’t affected you maybe you’d want to test 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

24. Enjoy The Adult Playground At Kanya Lounge 

Another activity we recommend for 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 bucket of beers can be enjoyed in the bar and lounge area while you’re at it.

25. Check Out Logan Square’s Gaming Paradise

Another fun-filled hideaway can be found in Logan Square. Midlane E-Sports is Chicago’s newest Esports venue providing both the group gratification of days gone by and the luxuries of modern technology. With high-end gaming computers, the latest consoles, tournaments, viewing parties, social gatherings, and a service bar it is the perfect gaming hideout for gamers of all genres. Drinks and Game Night at Midlane! tickets offer exclusive gaming sessions with specialty-themed cocktails for just $22.

26. Explore Illinois’ Natural Wonders For Earth Month

[Image from Instagram / @jwjackson]
Maybe you’re the sort to be outside rather than in which case there is no better time to be exploring the great outdoors. We’re in the heart of spring, which means optimal weather should be coming up for venturing out into the wilderness and igniting our wanderlust while reconnecting with nature. It’s also Earth Month for added incentive!

The natural spectacles of Illinois are often overlooked considering the wide range of incredible landscapes across the United States. 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. Here are 7 natural wonders of Illinois that you can visit while international travel is off the cards.

  • 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

27. Look Out For The Blood-Red Total Lunar Eclipse

Image from Unsplash / @lefty_kasdaglis

One natural spectacle does not require venturing to different parts of the state and can be found in the skies above Chicago this month. After the sensational pink super moon we saw at the end of April, a second supermoon will be occurring on 26 May 2021, but this will be overshadowed by an even bigger astronomical event – a total lunar eclipse. The May supermoon will appear blood-red in the sky as it’s obscured by the Earth’s shadow.

For the best views, it’s always recommended to head to places with as little light pollution as possible. If you’re living in the city you’ll still be able to view it but if you’re prepared to make an adventure of it use this light pollution map to guide your way to the most optimum spots for viewing.

28. Reserve A Spot At The Little Mermaid-Themed Cocktail Bar

It’s always good to have something to look forward to down the line and this unique mermaid cocktail party is an event that will have you leaving the city streets behind for a whole new world.

What are you willing to give up for the chance to drink with mermaids? Your voice, your heart’s desire… maybe your very own human form? Luckily, all your nautical fairytale dreams can come to life without having to sacrifice anything you hold dear to your heart. The Little Mermaid Cocktail Experience has plans of splashing its way to Chicago in June 2021, and you’re invited to witness this timeless tale like never before! Get your tickets here, and be the first to enjoy the iconic event!

29. Secure A Space At Drive ‘N’ Drag Saves 2021

For something a little sooner, Drive ‘N’ Drag Saves 2021 is coming to Chicago next month and tickets are now on sale. The ladies will perform live on a giant stage in front of attendees’ cars for a show that promises, extravagant lighting, fabulous attire, and jumbotron LED screens. The sound will be broadcasted both from the stage and via an FM radio that you’ll be able to tune into once you arrive at the venue, plus there will be a concert-quality light show and gourmet food trucks with food available for purchase.

30. Secure A Ticket To ARC Music Festival

The end of 2021 is lining up to be something truly special and to add to the impending elation as life heads back to the way it was, a new festival is coming to Chicago merging world-renowned acts with local prodigious talent. Of all the events to look forward to Chicago’s inaugural Arc Music Festival is one to certainly have on your radar.

ARC Music Festival will take over Union Park this Labor Day weekend with a brand new festival that will pay homage to Chicago’s house music roots and kick off post-pandemic delirium.

There will be sets from Swedish producer Eric Prydz, Canadian duo Bob Moses, British duo CamelPhat, and the Australian producer FISHER amongst other acclaimed artists.  Meanwhile 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.

Tickets are now out for the much-anticipated Labor Day weekend festival!

[Featured image from Shutterstock]

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