It’s June and that can only mean one thing– the gateway to summer is here! Memorial Day Weekend has come and gone, giving Chicago its first taste of summer festivities. There’s plenty more where that came from.
From exhilarating interactive experiences to aquatic adventures, here are some of the best things to do this June in the Windy City.
1. Celebrate Pride Month
First of all, this month is dedicated to celebrating our wonderful LGBTQ+ community. Pride Month is celebrated each year in June to honor the 1969 Stonewall Uprising in Manhattan, a tipping point for the Gay Liberation Movement in the United States.
Today the country celebrates with pride parades, picnics, parties, concerts, and much more. Take time this June to explore all the amazing things the local LGBTQ+ community has done and continues to do throughout the month, and support them!
You can find a roundup of events, happenings, and more going on for 2023 Chicago Pride Month here.
2. See the world-famous umbrella sky project
Pride celebrations aren’t the only place you’ll find multi-colored displays this month. Though not strictly Chicago, The Umbrella Sky Project art installation has taken over Elmhurst filling the sky with bright floating umbrellas.
The prismatic art installations are only staying up for summer so it is worth getting out there when you can and taking in the canopy of color!
3. See Morton Arboretum’s new range of sculptures
A new exhibition has opened at the Morton Arboretum featuring a collection of brand-new towering arbor-inspired sculptures. Titled “Of the Earth”, the exhibition features five exclusive new works from Polish-American artist Olga Ziemska and replaces those on display for Human + Nature.
Opened on May 26 “Of the Earth” is the largest exhibition of artist Olga Ziemska’s work to date and has been created exclusively for Arboretum visitors.
According to an official Morton Arboretum release, Ziemska’s sculptures have been predominantly created from reclaimed tree branches and other natural materials gathered from various locations throughout the Arboretum’s grounds.
4. Catch a weekly Navy Pier firework show
Another feast for the eyes can be found above the waters of Lake Michigan this month. Navy Pier kicked off its summer programming on Memorial Day Weekend with a superb summer fireworks show completely free of charge.
Throughout June there will be firework displays every Saturday at 10 pm and every Wednesday at 9 pm through Labor Day weekend. Onlookers can find a spot anywhere on the pier or nearby to take in the completely free dazzling display.
5-7. Take a cruise
If you’re a firework fanatic and want to experience the displays in style whilst also creating memories, the Fireworks Booze Cruise! is the perfect way to make it an unforgettable evening.
Enjoy a live DJ set spinning the best Top 40, EDM, and hip-hop hits whilst taking in breathtaking views of Chicago’s architecture and the sunset before being treated to unobstructed views of the Navy Piers Fireworks show from the waters of Lake Michigan!
Of course, there are multiple ways to celebrate the warmer weather with many booze cruises taking place this summer. Float down the Chicago River admiring the views provided by Chicago and the sounds provided by DJ Tecknique at both Sunset Thursday Booze Cruises and Sunday Funday Booze Cruises.
Grab tickets to one of the many Chicago cruises here.
8. Kayak down the Chicago river
After shutting down for the winter season, Urban Kayaks have now reopened their Riverwalk and Monroe Harbour locations kicking off the spring and summer seasons of kayaking.
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 magical and truly unforgettable activity.
9. Watch the Art on theMART projections
A truly unique June evening can be had by combining kayaking with the Art on the MART projections.
Holding the title of the largest permanent digital art projection in the world, Art on theMART attracts thousands to the Riverwalk every week by firing up 34 digital projectors and showcasing work from both renowned artists and local talent on the 2.5-acre river-façade of the Merchandise Mart.
The ART on The MART is currently celebrating its 5th Anniversary with new commissions by internationally renowned artist Derrick Adams and projections of new work by local Chicago Public Schools (CPS) seniors.
Spectators can watch two free 30-minute programs of projections nightly throughout most of the year from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
More information can be found here.
10. Head to this magical Harry Potter™ experience
School is nearly over, but if you’re looking to step into the Hogwarts™ School of Witchcraft and Wizardry for some magical potions classes and so much more, you’re in luck! Harry Potter™: Magic at Play in Chicago recently extended until Labor Day, so you have the entire summer to explore this experience. The boat ride to Hogwarts™, stepping into the Great Hall, and sipping on an endless supply of Butterbeer are just a few things you’ll enjoy at this limited-time adventure on the Magnificent Mile!
11-15. Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series is providing an array of breathtaking spectacles in the Windy City. Talented musicians will be performing at extraordinary venues all over Chicago offering guests the chance to marvel at the enchanting combination of flickering candles and melodic sounds.
Here are some of our favorite Candlelight concerts taking place this month:
- Candlelight: Featuring Vivaldi’s Four Seasons & More at Wicker Park Lutheran Church on June 3
- Candlelight: A Tribute to Taylor Swift at Stan Mansion on June 8
- Candlelight: A Tribute to Juan Gabriel at Salvage One on June 9
- Candlelight: The Best of Hans Zimmer at Music Box Theatre on June 15
- Candlelight: A Tribute to Radiohead at Stan Mansion on June 15
- Candlelight: A Tribute to Adeleat Stan Mansion on June 29
See the full list of candlelight concerts taking place in Chicago here.
If you can’t decide on a concert but want to ensure you attend one or need to buy a gift for somebody special Candlelight gift cards are really easy to use and valid for any Candlelight event in the U.S. making it a unique gift for both friends and family.
Get your Candlelight Gift Card here.
16. Attend a Concert Under The Stars
AIRE Rooftop at Hyatt Centric The Loop Chicago
Concerts Under the Stars is another terrific outdoor musical experience taking place this month.
Both Sinatra Under the Stars at AIRE on June 4 and ABBA Under The Stars at AIRE on June 18 provide two enchanting events this month.
17. Send your senses soaring with a Dining in the Dark experience
Dining in the Dark experiences have returned to Chicago and they’re selling out quickly! Engage your taste buds at a unique night out as you indulge in a delicious three-course meal at the exclusive ‘Dining in The Dark’ dinner parties.
Take your date night to the next level or enjoy a surreal experience with friends, tempting your senses with dark surroundings to focus on more important things like the exquisite food and wine pairing you’re about to have at Hubbard Inn.
Diners can choose vegan, seafood, or red meat options, enjoying a starter, main entree, and dessert.
Grab tickets to a Dining in the Dark experience here.
18. Kick back with goats and beer
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.
19. Head down to the Grand Cabaret After Dark speakeasy
Down in the basement of West Loop’s Porkchop visitors will find a top-tier speakeasy experience in the form of “Grand Cabaret After Dark” where a roster of rip-roaring revelry awaits.
There is always something happening at the West Loop speakeasy throughout the weekend. Featuring live music of classic and contemporary jazz, bluegrass, and country by the Chris Ussery Trio, you’ll be able to sink into your seat as the music swirls around you on Saturdays at Grand Cabaret After Dark and then soothe your Sunday scaries with Boozy BBQ Drag Brunches on Sundays.
Check out all the chaos going on at Porkchop’s Grand Cabaret After Dark here!
20. The Empire Strips Back: A Burlesque Parody
Of course, Grand Cabaret After Dark is far from the only speakeasy experience in Chicago. Let us deliver you to the dark side! With comedy and allure, loving detail, and hilarious parody, The Empire Strips Back drops classic Star Wars characters into the world of burlesque.
Be prepared for some seriously sultry Stormtroopers, a dangerously enticing Boba Fett, some tantalizing Twi’leks, a delightfully luke-warm Taun Taun, a lady-like Skywalker, the Droids you are looking for, and much, much more!
Grab tickets to The Empire Strips Back: A Burlesque Parody here.
21. Kick back in an AMC movie theatre
Talking of blockbuster movies, we’ve just come out of awards season with so many fantastic movies of all kinds from across the planet highlighted over the last several weeks. There are so many to see at the moment and there’s no place better to experience them than at AMC Theatres®.
Whether it’s a rainy afternoon or a special date night, all the best critically-acclaimed creations, comedies, action flicks, and everything in between can be enjoyed at a discount in Chicago, and nationally, with an AMC black ticket.
Grab discounted tickets to a movie showing here.
22. Enjoy some of the extraordinary exhibitions taking place in Chicago this year
One of Chicago’s most impressive qualities is undeniably its collection of world-class museums and the array of exhibits they offer. This year there are a whole host of new extraordinary art exhibits coming to the Windy City.
Art, science, and human connection have a truly transformative power, and now, after the tumultuous and unprecedented years that we’ve just endured, it’s time to remember that.
23. Browse some of the world’s most famous artworks for free
One of the oldest and largest art museums on the planet, the Art Institute of Chicago is undoubtedly one of the city’s most renowned museums. Since its founding in 1879, the Art Institute of Chicago has flourished into one of the most recognized art museums in the world.
The museum is permanently home to over 300,000 works of art including such masterpieces as American Gothic by Grant Wood, Nighthawks by Edward Hopper, A Sunday on La Grande Jatte by Georges Seurat, The Bedroom, 1889 by Vincent van Gogh and The Old Guitarist by Pablo Picasso.
According to the Art Institute of Chicago website, “admission will be free for Illinois residents on Thursday evenings, 5–8 p.m., May 18–August 31, 2023.”
24. Get free entry to Adler Planetarium on a Wednesday
Another of Chicago’s famed attractions, The Adler Planetarium, underwent a huge revamp during a two-year Covid-19-induced hiatus and now boasts a brand new telescope in the Doane Observatory which holds the title of the largest public telescope in the state.
As well as a new observation park, the planetarium has a shiny new roof giving the 80-year-old dome an iconic new glow. The best news of all, however, is that upon its reopening the planterarium announced that Illinois residents will be able to enter for free every Wednesday evening from 4-10 pm for the foreseeable future provided they bring proof of residency.
More information and tickets can be found at adlerplanetarium.org.
25. Sip on Craft Brews at Lincoln Park Zoo’s annual festival
Another landmark offering something special this month is none other than Lincoln Park Zoo. On June 17 guests can enjoy the 8th annual Craft Brews at Lincoln Park Zoo and sample over 100 beers and ciders while wandering around the expansive zoo.
See your favorite animals, enjoy live entertainment, and play a lawn game or two. Make sure to stop by and see the new lion clubs!
More information can be found here.
26. Spend a Sunday at Maxwell Street Market
Maxwell Street Market, Chicago’s longest-running open-air market, first debuted back in 1912 has returned for its 111th summer stretch with handmade crafts and undetected treasures.
Open every Sunday at 800 South Des Plaines Street from 9 am to 3 pm through to Sunday, October 29, shoppers can expect a Sunday of spirited live music, and sensational street food as well as an eclectic array of bric-à-brac.
27. Shop local vendors at Hyde Park Art Center’s Farmers Market
The Art Center in Hyde Park is hosting a summer farmers market series that includes hands-on art-making activities and plenty of shopping opportunities at local vendor booths.
The market will pop up on Sunday, June 4 from 9 am to 1 pm and then again on July 9 and August 13.
More information can be found here.
28. Celebrate the summer season at Lincoln Square’s annual Maifest party
Over in Lincoln Square, the bustling neighborhood is once again hosting a beer-fueled party to celebrate the area’s German heritage from June 1-4.
Maifest will be filled with giant pretzels, steins, and dancing, the neighborhood event lasts all weekend and definitely includes plenty of live entertainment.
More information can be found here.
29. Celebrate Greek heritage at Lincoln Park’s annual Greek Festival
From Germany to Greece, head over to St. George Green Orthodox Church for a spread of delicious gyros, feta, and more as the church celebrates its annual Greek Festival with traditional music, dancing, and plenty of local shopping vendors!
The family-friendly event has it all happening at Sheffield and DePaul from June 2-4!
More information can be found here.
30. Take part in the Windy City Hot Dog Fest
Portage Park is the place to be for Chicago hotdog aficionados. Local vendors from Chicago Doghouse to Byrons and more are coming out to win fan-favorite frankfurter in a competition.
Complete with live entertainment, craft vendors, a hot dog eating competition, and even a parade, this hot dog-centric festival is a can’t-miss celebration of Chicago’s legendary food staple on the first weekend of June.
More information can be found here.
31. Celebrate Father’s Day at The Pendry Hotel
Head to the downtown hotel this Father’s Day on June 18 for an al fresco cocktail celebration. Taking place at the historic Art Deco Carbide & Carbon building (230 N Michigan Ave.) on Magnificent Mile, head to the rooftop to enjoy French-inspired drinks and botanical absinthe-infused cocktails
The newly reopened rooftop bar is hosting the opening event with eight seasonally inspired drinks, pizza to snack on, and plenty of seasonal bites! Enjoy the full bar, wine, and rosé along with the beautiful view.
More information can be found here.
32. Enjoy a glass of bubbly at Pioneer Court’s summer champagne takeover
The #1 Champagne in France, Champagne Nicolas Feuillatte is coming to Chicago this month to unleash all the bubbles! Taking over Pioneer Court (401 N Michigan Ave.), see the space transform into a French garden and labyrinth featuring exciting Instagram-worthy moments.
Like a giant cork art installation, bubble displays, and yes, lifesize bubbles! Anyone over 21+ can enjoy free tastings at this luxe summertime event taking place June 8-11.
More information can be found here.
33. Head to the Heatwave Music Festival at Northerly Island
The hottest house music festival is taking place this summer on the incredible Museum Campus during the second weekend of June (10-11). Now in its second year, the hot summer lineup will include house music headliners like Gryffin, Slander, and GRiZ.
Along with the exciting daytime performances, there will also be a host of cool afterparties!
Keep an eye out for ticket deets here.
34. Attend the Lyrical Lemonade Summer Smash Music Festival
Lyrical Lemonade is bringing its best and brightest hip-hop stars to the stage at a Bridgeview stadium this summer. From Kid Cudi to Future and more, this incredible festival will be an epic look at the future of hip-hop and a celebration of the genre for three days starting Friday, June 23.
More information can be found here.
35. See a drag performance at the Chicago is a Dollhouse celebration
The lauded Chicago drag festival is back this month, just in time for Pride. Now under a new name, Chicago is a Dollhouse, the annual celebration is free this year marking its return to in-person events at the Cheetah Gym in Andersonville (5248 N Clark St).
Previously, the celebration was moved online due to the pandemic. Now back, celebrate Chicago’s drag scene, and see epic performances from kings, queens, and 35+ performers on Friday, June 23.
More information can be found here.
36. Go insta-famous with the Chicago Instagram Walking Tour: Most Famous Spots
If you love architecture and snapping photos a Chicago walking tour offers a great combination of the two. However, if for you it’s all about capturing those Instagrammable moments and you don’t want to hold up the crowd this tour is ideal.
A local host will take you along a scenic tour of Chicago’s most famous spots with timely breaks to snap away so get ready to take in all the architectural feats, hidden gems, and picturesque landmarks you can imagine. The half-day tour is sure to inspire a caption or two and is jam-packed with endless breathtaking views, exciting fun facts, and memorable moments.
Learn more and grab a ticket for an unforgettable tour here.
37. Brunch to your heart’s content
If you’re in need of an instant mood boost, searching for a group Sunday Funday activity, or looking to cure a hangover from the night before, brunch is the solution to all problems.
Luckily Chicago has an abundance of seriously good morning eats and here we’ve compiled the best of the bunch!
Find our list of the best brunch spots in Chicago here.
38. Sample the best cocktails in Chicago
Whether you’re treating yourself to brunch in Chicago, kicking back on a Chicago patio, or enjoying drinks out at one of Chicago’s many bars and restaurants, you can be sure a finely-crafted cocktail is only seconds away.
From top-notch margaritas to more innovative cocktail concoctions and everything in between, the Windy City and its abundance of revered mixologists have the answers to whatever it is you’re after.
We’ve recently filtered through the noise to round up the very best cocktail bars in Chicago based on our own experiences at Secret Chicago, our reader’s most popular choices, and a scrupulous assessment of settings and drink quality.
Find our up-to-date list of the very best cocktail bars in Chicago here.
39. Kick back at a revered brewery
If craft beers are more up your street than a fruity cocktail, worry not for Chicago has an abundance of internationally-acclaimed breweries.
Frequently recognized as one of the best beer cities in the country, our seasoned and inventive beer scene has produced so many fantastic breweries and taprooms in Chicago that we’re spoilt for choice.
There are now over 200 breweries big and small across Chicagoland meaning there are plenty of opportunities to enjoy a finely-crafted beer in a range of different environments whatever the weather.
To make sure you’re checking out the best of the best we’ve here rounded up the 10 best breweries, brewpubs, and taprooms in Chicago. Cheers!
40. Buckel up for a Drunk Shakespeare show
On that topic another brilliant Chicago 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.
41. Chuckle away at Chicago comedy show
If you’re looking for a chuckle there’s no place better for that than at a Chicago comedy show. Famous for its production of funny guys and girls. Chicago has some of the best places to see a comedy show in the country.
At Laugh Factory Chicago some of today’s biggest names and local comedians are delivering something for every taste and style throughout the year.
Grab tickets to a show at Laugh Factory Chicago here.
42. Peruse the magnificent street art murals of Chicago
Chicago’s street art and graffiti scene has continued to thrive in Chicago over the last decade. New pieces pop up all over the city every week, some of which are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now part and parcel of the Windy City’s identity.
Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for racial equality, celebrate different heritages, and honor the essential workers of our societies during turbulent times. Hunting down the must-see street art murals in Chicago is a rewarding experience any time of the year.
We’ve rounded up our top 25 most amazing murals in Chicago so you can navigate your way around the best of the best and learn about its history and the inspiration behind some of Chicago’s famous murals.
Alternatively, you can also jump on an Offbeat Street Art Tour of Chicago and be guided by a seasoned street art enthusiast!
43. Unleash your inner artist at a Spray ‘N’ Sip urban art workshop
If perusing Chicago’s incredible street art has your creative juices flowing there’s no better place to let your inner artist run wild than at Chicago’s incredible BYOB Urban Art Workshops.
Taking place weekly within Studio W.I.P. at The Chicago Kedzie Plaza, there’s no pressure and no presumptions, just creativity and fun flowing in all forms. Trained professional artists will teach you the tricks of the trade as unleash your inner artist on a mural with your favorite drink in one hand and a spray can in the other.
Grab your tickets to a Spray Paint ‘n’ Sip Urban Art Workshop here.
44-45. 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!
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 or a donut tour here.
46. Play soccer in the sky at Chicago’s first-ever rooftop soccer pitch
Much to the excitement of soccer fans all around the city, an exciting new soccer venue opened in Chicago last year taking the city’s soccer scene to new heights.
Located atop the NEWCITY parking structure in Lincoln Park, the Skyline Pitch opened as “Chicago’s 1st rooftop soccer venue for guests of all ages to train, play, and celebrate the game of futsal and soccer with an unmatched view of the beautiful Chicago skyline.”
First thought to be a temporary fixture, the skyline pitch and its variety of leagues have returned for a spring and summer season now running through to October.
47. Jump into spring with indoor skydiving
Recent years have reminded us that we should be active, try new things, and make the most of the adventures and experiences that are available to us and one thing that always finds itself on bucket lists worldwide is skydiving.
Now, we’re not saying jump out of a plane in the freezing skies above Chicago, but we are saying give it a go in one of Chicago’s indoor centers to get a taste of what it is like and why it is such a popular ‘do before you die’ activity.
With a state-of-the-art iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, Chicago is home to two conveniently located cutting-edge centers where kids and adults can get the same sensation you’d get 12,000 feet up in the sky.
If the experience has you wanting more you can always test your vertigo above Chicago’s skyscrapers at one of the world’s largest skydiving resorts in Skydive Chicago and boast that you’ve jumped out of a plane above the Windy City.
48. Head out of the city and see Illinois’ natural spectacles
Heading out into the wilderness is another way you can enjoy a fulfilling experience without paying more than the cost of travel. If you’re one who enjoys being surrounded by nature then heading out to the quiet of Illinois’ natural beauty is a great spring 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
49. Stay in a Starved Rock Getaway cabin
For an even more prolonged experience in nature. Getaway House is a chain of tiny cabin hideaways helping people in big, bustling cities like Chicago, DC, LA and NYC, disconnect from their busy city lives with restorative stays in the middle of nature.
One of the aforementioned spots, Starved Rock State Park, has just opened a selection of minimalistic cabins with floor-to-ceiling windows allowing guests to wake up fully immersed in the wilderness. Located in lush landscapes and with minimalistic yet comfortable designs, they offer the perfect escape for those wanting to disconnect from busy city lives with restorative stays in the middle of nature.
More information can be found here.
50. 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 and there is no better time than spring.
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.