The Midwest’s largest city, Chicago, is the ideal place to turn your ordinary date night into an extraordinary excursion everyone will envy. With 26 miles of lakefront, 25 beaches, 600 parks, 200 music venues, and more than 7,000 cocktail bars and restaurants, there are countless places to take a date in the Windy City. But hopeless romantics looking for the best date options in Chicago know they need more inventive ideas to keep their loves happy.
From budget-friendly fun to superlative splurges, this curated list of creative Chicago date ideas has something for everyone. From long walks hand-in-hand along the shores of Lake Michigan to a spa day pampering each other at Ancient Baths, these ideas are sure to impress. Channel your inner cupid and invite your crush to your first (or 40th!) date at one of these desirable Chicago date destinations.
Get dressed in cocktail attire and spend a magical date night out in Chicago witnessing the magic of third-generation magician and mind reader, Dennis Watkins, who has been performing magic at the Palmer House Hotel for years. Fewer than 50 guests are ushered into a room to watch The Parlour Magic, Chicago’s longest-running magic show. After the 90-minute show, up to 12 magic fans can go to The Encore Room for a bonus 25-minute magic show held around a card table. During this more intimate affair, guests are treated to Watkins’ sleight of hand close-up magic and a question-and-answer session.
Have a spa date day (or night) with your amour at AIRE Ancient Baths. Located in a restored factory in River West, this bathhouse is replete with traditional Roman, Greek, and Ottoman baths and rituals. Amenities include hot, warm, cold, and ice baths, an invigorating jetted bath, aromatherapy steam rooms, and a salt bath along with a menu of massages for an ah-mazingly relaxing date.
Invented in the 1960s, WhirlyBall is a mix of hockey, lacrosse, and basketball. Teams of five players carry scoops and drive Whirlybugs — electric bumper-car-like vehicles—during fast-paced 10-minute matches. This makes our list of top fun date ideas in Chicago because you can team up with your partner or compete against each other as you use your scoop to hurl Wiffle balls at targets to score goals.
Remember that scene where Ferris and his friends lean onto the glass of the Sears Tower high above Chicago? You too can get a bird’s eye view of the Windy City 1,353 feet up at the Skydeck of the now-named Willis Tower, the third tallest building in the Western Hemisphere. Step onto one of the glass-bottom boxes that extend 4.3 feet from the Skydeck for a kiss your date won’t soon forget.
Combine your date with a workout during a romantic row down the Chicago River. With a launch at East Bank Club, Wateriders is a short paddle from downtown Chicago. The company offers guided group paddles and kayak rentals by the hour. From a leisurely sunset paddle past Chicago’s famed skyline to a three-mile nighttime ride down the River timed to see the Navy Pier fireworks, this top-notch Chicago date idea is certainly one to remember.
Add extra spark to your relationship by practicing teamwork and problem solving while creating a robot. During this interactive robot-making class, you will learn how to build a simple circuit, a robot, and brave the love tester at Robot City. Couples can choose from a dozen different DIY robot kits to create their own robot to take home. While building the robot, sip on beverages and snack on popcorn delivered by Omnibot 2000, play a round of robot trivia, and enjoy a robot-themed movie that plays throughout the evening.
Cuddle up with your date in the dark leather booths at Au Cheval where you can dine à deux in a sophisticated diner-style setting. The signature cheeseburger with fried egg is a must, as is the root beer on draft. There’s often a line out front, but it’s worth the wait at this sweet spot that doesn’t take reservations, perfect for a spontaneous romantic rendezvous.
See if your love is written in the stars at Adler Planetarium. On select clear nights, up to 12 people can snag a spot to peer through Chicago’s largest publicly accessible telescope to see Chicago’s starry starry night. You will also learn how telescopes work, get tips for finding constellations, and try a working replica of astronomer Galileo Galilei’s handmade telescope.
This tried and true Chicago date idea makes everyone’s bucket list, and for good reason. What started with children’s improvisational games has become one of the most influential comedy spots in the world. Since opening in 1959, The Second City has hosted six decades of laughter from the world’s most famous comedians. The line-up is ever evolving and it’s easy to get tickets to enjoy one or more funny dates.
There is no menu at this Lincoln Park restaurant that excels at molecular gastronomy. The three-starred Michelin restaurant, Alinea, is perfect for a splurge, a special date night, or to pop the question. The multi-course tasting menu prepared by Chef Grant Achatz ranges from $295-$435 per person and reservations are typically released two months in advance.
Whether you like to run, bike, rollerblade, or walk, the 18-mile Lakefront Trail is a perfectly paved path that runs from Ardmore Street on Chicago’s north side to 71st Street. Flanked by Lake Michigan on one side and the city’s eastern skyline on the other, the trail passes many parks, beaches, and restaurants. This rad Chicago date idea because along the way you can play tourist and visit attractions like Soldier Field, Navy Pier (see more below!), and the Peggy Notebaert Nature Museum.
Known as the People’s Pier, the options for dates abound at Navy Pier. Take a ride on the Centennial Wheel and soar nearly 200 feet over Chicago, rent a tandem bike or quadcycle to pedal the Pier together, and clink glasses at Offshore, the largest rooftop venue in the nation. During select weeknights in the summer and other evenings throughout the year, fireworks light up the night sky, adding more ambiance to an already awesome date.
Founded in 1974 in Highland Park, Steppenwolf Theater has been presenting award-winning plays for five decades. The professional theater company has 49 ensemble members who present a variety of productions each season at their theater on North Halsted Street.
Chicago is famous for many foods, including deep dish pizza, hot dogs, and doughnuts. Stroll with your sweetie to sample the best portable treats, from Chicago deep dish pizza at Gino’s East, Lou Malnati’s Pizza, and Pequod’s to hotdogs from Byron’s Hot Dogs, The Wiener’s Circle, and Superdawg and doughnuts from shops like the Doughnut Vault, Stan’s Donuts, and Do-Rite Donuts.
Settle in for a night of creative, cutting-edge cocktails at The Aviary. Grant Achatz and Nick Kokonas’ “redefined” cocktail bar in the West Loop of Chicago consistently pushes boundaries with every drink ingredient, down to the hand-formed and hand-chipped ice painstakingly assembled. If this is the date idea of your choice, make reservations and opt for the signature five-course cocktail tasting menu paired with light bites like a massive crispy pork skin. Cheers!
Dig this list off fun date ideas in Chicago? Check out our list of uber-romantic date ideas for Toronto!