Published on 11/14/2023 at 4:54 PM
When the sun sets, Chicago awakens. Whether you want to party until the wee hours of the morning or partake in a culturally enriching experience, Chi-town has a happening nightlife scene. Yes, the Windy City has a slew of epic restaurants and bars that stay open late into the evening, but these activities and tours are sure to kick off your vacation on a stellar note. Let a third-generation magician blow you away, or head to a jazz club for some juping and jiving, or hop on a cruise that whisks you past a fireworks display at Navy Pier. Keep reading for our top evening activities in Chicago.
By day, play on the land (okay, maybe take a spiffy architecture boat tour, too). Come nightfall, hit the Chicago River or Lake Michigan for some memorable jaunts with Chicago City Cruises. The boat tour outfitter has a wide range of itineraries running the gamut from a two-hour “Sights & Sips” cocktail cruise along the Chicago River to a three-hour plated prix-fixe dinner along Lake Michigan with fireworks. Whatever trip you book, all boats provide climate-controlled interior decks, plenty of seating, and cinematic vistas of the Chicago cityscape. If you make the reservation on behalf of your entire party to lock down a date and a time, have your pals pay you back with Zelle® swiftly and safely.
Specifically, Rock and Roll Hall of Famer Buddy Guy’s beloved Blues club, where you can 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 roots). Earlier evening sets are free while later sets have a cover charge and, since all tickets are general admission and seating is on a first-come-first-serve basis, arrive early if you want to snag a great seat.
For another, well, magical evening try this so-called “magic speakeasy” located behind a 1940s-era commercial laundromat (as in, you’ll have to step behind washer-dryer units to get inside). The beautiful theater and lounge is a sprawling 7,200 square feet and patrons can nurse a cocktail at the 1930s-inspired speakeasy performance bar, sit down for quite the spectacle at the 107-seat Harry Blackstone Cabaret Theater, and see a smaller post-show performance at the 43-seat The 654 Club gallery. We don’t want to give too much away but it’s safe to say this outing will be one for the books (quite literally, too, as the venue has a library of magic literature and memorabilia).
Put down the pickleball racquets and try the unique sport of WhirlyBall. Celebrating its 30th anniversary in Chicago this year, this game is played on modified bumper cars called WhirlyBugs. The bugs have a max speed of four miles per hour — the game employs elements of lacrosse, hockey, and basketball. You’ll need at least four people for a match and you’ll use a scoop to pick up and throw the Whiffle ball as you fight for winners’ bragging rights. Speaking of which, losers should have to pick up the tab at WhirlyBall’s The Pivot Room for post-game brewskis and grub. The deck, complete with fire pits, is also a lovely place to say cheers after you're done WhirlyBallin'. Standouts include buffalo cauliflower wings, drunken shrimp tacos, the panini grilled cheese and the boozy brownie extreme for the 21+ set for dessert. Excluding food and drinks, you can reserve a court and all the gear you’ll need for $250 per hour for up to 10 people, which you can split easily on Zelle® in advance of game-time.
Time is ticking, friends. Fox in a Box is 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 mission such as escaping from prison or saving the world. (Hint: Communicating effectively with your team goes a long way.) Pricing depends on the date and time of your booking 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 groups of three-to-six people but a large group can rent out the entire space.