12 Unique & Fun Date Ideas in Chicago (2024)

Chloe MullinerChloe Mulliner
Chloe Mulliner
6 min read
Published in Date Night 


    Need some inspiration when it comes to fun date ideas in Chicago? These new and unique ideas are sure to impress your date!

    Chicago is an incredible city with so much to do, but it’s easy to get into a rut when it comes to brainstorming date ideas. Maybe your go-to first date spot has begun to feel a little lackluster lately. Or perhaps you and your partner are tired of hitting up the same haunts every Friday night. 

    Whatever the case, don’t fret. There are countless amazing date spots in Chicago you’ve yet to experience—and they are sure to impress your date!

    Whether you’re looking for a casual, laidback idea or one that pulls out all the stops, we’ve got you covered. Below, we’ve listed 12 of our favorite Chicago date ideas, from taking an architecture tour aboard a river cruise to catching an independent flick at a vintage movie theater. 

    Pick one (or several!) of these ideas, and you’ll be well on your way to landing a follow-up date. 

    1. Float Around the Lagoon

    Can you really call it a date if you’re not cruising around in a swan-shaped boat? We think not! Anytime between May and September, head to Humboldt Park Lagoon, where you can take a swan-themed paddle boat for a spin. Known as a universal symbol of love, swans are famous for staying with one special mate for life, so let them be your inspiration as you paddle around the lagoon in a boat made for two. 

    1. Take a Stroll through the Garfield Park Conservatory

    Interested in some date ideas for introverts? Then we recommend planning a peaceful afternoon at the Garfield Park Conservatory. Considered one of the nation’s largest botanical conservatories, it’s an ideal date spot in Chicago for those seeking a quiet escape from the hustle and bustle of city life. 

    Here, you can both marvel at the “landscape art under glass.” From the Fern Room to the lily ponds, you’ll lose yourselves in the magic of the surrounding plants, flowers, and trees. When planning this date, just be sure to make reservations in advance.

    1. Make it a Double Date

    If you are both the proud parents of some well-behaved pups, bring them along on your date and spend an afternoon down at Montrose Dog Beach. You and your date will have a blast on the beach while your dogs get to know each other, too, as they play fetch and dig holes in the sand. But even if you don’t have a dog in tow, you can still venture down and watch the four-legged ones frolic around the shore. 

    1. See Something Out of the Box at the Music Box Theatre

    Skip the mainstream movie theater and instead plan date night at the Music Box Theatre, featuring off-beat independent films, from foreign flicks to cult classics. This iconic movie theater has kept its original architecture and charm from 1929.

    If you go with this date idea, be sure to arrive an hour or two before the show and head to the Music Box Lounge + Garden. You two can sip on movie-themed cocktails while watching VHS movies inside or enjoying some fresh air on the patio until showtime. 

    1. Kickback at the Catcade

    If you’re in search of the purr-fect date spot in Chicago, look no further than Catcade. As its name suggests, it’s part arcade, part cat rescue center, where all the cats and kittens are adoptable. With the cost of admission, you and your date can spend an hour playing games and snuggling with the cats (just be sure to make advanced reservations). 

    And just think, if one of you ends up giving a cat its forever home, it’s sure to be one date that will go down in the history books. 

    1. Search for Some Vinyl at Dusty Groove

    If you and your date share an interest in music, then Dusty Groove might be up your alley. This unique Chicago date idea involves venturing to this iconic record shop and browsing the eclectic selection of LPs, 45s, and CDs. Whether you’re into jazz, funk, soul, or disco, this record mecca has it all. 

    As for your date, pick out your favorites on vinyl, grab some takeout from one of the delicious eateries in East Village, and have a listening party back at your place.  

    1. See Some Wonders at the Magic Lounge

    Do you believe in magic? Well, you just might after seeing some of the amazing acts at the Magic Lounge. 

    Make reservations for date night in Chicago at this speakeasy performance bar that showcases Chicago-style magic tricks dating back to the early 1900s. You and your date will be absolutely amazed at the mysterious and magical performances that unfold on stage. 

    1. Explore a Quirky Museum

    Looking for a good, quirky date idea? Skip some of the city’s more famous museums and instead check out some of the lesser-known (yet equally fascinating!) exhibits. 

    After all, Chi-Town is teeming with quirky and off-beat museums, from the Leather Archives and Museum and the International Museum of Surgical Science to the Busy Beaver Button Museum and the Money Museum. When you check out one of these cool date spots in Chicago, you’ll both have plenty to talk about afterward!

    1. Sip Sodas

    Back in the day, soda shops were the ideal spots for taking a date out on the town, so why not pay homage to this old-school date idea? 

    Spinning J is a vintage-inspired bakery and soda fountain where you and your date can belly up to the marble bar and order sweet drinks like a strawberry rhubarb phosphate or chocolate egg creme. And if you want to further sweeten the deal, add vanilla ice cream to make it a float!

    1. Listen to Jazz at the Green Mill

    When planning the ultimate date night in Chicago, check out the lineup at The Green Mill. This no-frills, cash-only cocktail lounge has long been a staple in the Windy City for legendary jazz performances, as it once featured major acts, from Louis Armstrong to Billie Holiday. However, it’s not all jazz-centric—this laidback lounge also features poetry slams on Sundays. 

    Whether you come for the jazz or the poetry, be sure to look for the booth where Al Capone used to sit, which is apparently just west of the short end of the bar. 

    1. Catch the Sunset from the Sky

    If you really want to plan a successful first date, head over to CloudBar for front-row seats to the sunset. This epic bar sits on the 94th-floor observation deck at Chicago 360, serving drinks, snacks, and some of the city’s best views.

    But if you really want to impress your date, get tickets for Tilt, which is considered Chicago’s “highest thrill ride.” It features a moving platform that swivels over the side of the building, showcasing a side of Chicago you’ve never seen before! If you’re both the adventurous type, this is definitely the date spot for you. 

    1. Take an Educational River Cruise

    The Architecture River Tour is easily one of our favorite Chicago date ideas. Led by the Chicago Architecture Foundation, this tour invites you to climb aboard a luxury boat and discover the stories behind the magnificent skyscrapers that line the city skyline. As you cruise along the Chicago River, you and your date will see these incredible buildings from a different perspective and learn all about their history. For an even more spectacular (and romantic!) experience, reserve the Evening River Cruise to admire the architecture during the golden hour. 

    When it comes to first date etiquette, no one ever said you have to stick with something boring. So, next time you’re planning a date night in Chicago, choose one of these unique ideas, and you’re certain to have a special time!

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