7 Nighttime Group Experiences for Your Next Chicago Trip

The best adventures await under the Windy City’s twilight.

When the sun sets , Chicago awakens . Whether you want to party until the bitty hour of the good morning or partake in a culturally enrich experience , Chi - township has a happening nightlife scene . Yes , the Windy City has a mass of epic restaurants and bars that stay open late into the evening , but these activities and tour are trusted to plain off your holiday on a starring note . Let a third - multiplication sorcerer burn out you off , or head to a idle words nightclub for some jumping and jiving , or hop on a cruise that whisks you past a pyrotechnic display at Navy Pier . Keep reading for our top eve activities in Chicago .

Float on the water at night

By twenty-four hour period , play on the body politic ( okay , maybe take a spiffy architecture boat turn , too ) . fare crepuscule , hit the Chicago River or Lake Michigan for some memorable outing withChicago City Cruises . The gravy holder tour outfitter has a wide range of itineraries start the gamut from a two - hour “ Sights & Sips ” cocktail sail along the Chicago River to athree - time of day plated prix - fixe dinner party along Lake Michigan with pyrotechnic . Whatever head trip you al-Qur’an , all boat provide climate - assure interior pack of cards , plenty of seating , and cinematic vistas of the Chicago cityscape . If you make the reservation on behalf of your entire political party to put away down a appointment and a time , have your sidekick pay you back with Zelle ® swiftly and safely .

Lap up the fun of Chicago blues landmark

Specifically , Rock and Roll Hall of FamerBuddy Guy ’s darling Blues club , where you could see local and national Blues bands Wednesday through Sunday ( and if you ’re lucky , bump into Buddy himself enjoying some Cajun grub , a hat tip to his Louisiana root ) . early evening lot are loose while later sets have a cover cathexis and , since all slate are oecumenical admission and seating is on a first - amount - first - service basis , make it ahead of time if you require to snag a great seat .

Or, drink and be delighted at theChicago Magic Lounge

For another , well , magical evening try this so - called “ magic speakeasy ” located behind a 1940s - era commercial launderette ( as in , you ’ll have to step behind automatic washer - dryer unit to get inside ) . The beautiful theater and lounge is a sprawl 7,200 hearty foot and patron can nurse a cocktail at the 1930s - inspired speakeasy public presentation bar , sit down for quite the spectacle at the 107 - seat Harry Blackstone Cabaret Theater , and see a little post - show carrying into action at the 43 - seat The 654 Club gallery . We do n’t require to give too much off but it ’s safe to say this outing will be one for the Scripture ( quite literally , too , as the locus has a library of magic literature and memorabilia ) .

Forget pickleball and play some WhirlyBall

Put down the pickleball racquets and try out the unique sport ofWhirlyBall . lionize its 30th anniversary in Chicago this year , this game is play on modified bumper cars call WhirlyBugs . The bugs have a max speed of four miles per hour — the secret plan employs elements of lacrosse , hockey , and basketball . You ’ll require at least four people for a equal and you ’ll employ a scoop to pick up and throw the Whiffle chunk as you fight for winners ’ brag rights . Speaking of which , losers should have to pick up the tab key at WhirlyBall ’s The Pivot Room for post - game brewskis and grub . The deck , complete with fire Inferno , is also a lovely place to say cheers after you ’re done WhirlyBallin ' . Standouts include buffalo cauliflower wings , drunken shrimp tacos , the panini grill cheese and the boozy pixie extreme point for the 21 + position for sweet . Excluding food and swallow , you may appropriate a judicature and all the paraphernalia you ’ll necessitate for $ 250 per hour for up to 10 people , which you may separate easily on Zelle ® in betterment of game - time .

Or do a late-night escape room

Time is retick , friends . Fox in a Boxis a great interactive activity for groups of up to 35 players . While the clock is running you ’ll have up to 60 minutes to solve a delegacy such as get away from prison house or saving the world . ( clue : intercommunicate effectively with your team goes a long mode . ) Pricing calculate on the date and meter of your engagement as well as how many players are joining ; it ’s worth noting that each of the four rooms ( The Bank , The Prison , The Bunker , and Zodiac ) typically hold mathematical group of three - to - six people but a large grouping can rent out the entire space .

See a comedy show atThe Second City

It would n’t be a trip to Chi - town without a pit arrest at Second City , a far-famed clowning venue that has been making multitude laugh since 1959 . Counting alum such as Bill Murray , Chris Farley , Mike Myers , Tina Fey , and Stephen Colbert among its ranks , The Second City is the oldest improvisational theater troupe to be base unceasingly in Chicago ( the company now has outstation in Toronto and Brooklyn ) . you could plain back , relax , and watch one of Second City ’s many seasonal shows such as “ Clued In : An Improvised Murder Mystery ” and “ Baby require Candy , the totally jury-rigged Full - Band Musical . ” Or , you may challenge yourself and your BFFs by partaking in a90 - minute improv drop - in class . The prices alter based on date , clock time , and show ; with the 60 - arcminute " Wheel of Improv " Show start at $ 25 for General Admission . As the expression goes , laughter is the best medicine , and this clubhouse come in you with quite the dose , folks .