Dinner and a movie? You can do better than that. Chicago is full of activities that make for a great date.
Distillery tour, then pie
Main attraction: KOVAL Distillery tour | 5121 N. Ravenswood Ave. 312-878-7988
Take an hourlong tour of one of Chicago’s oldest distilleries, where you’ll taste test Koval’s organic whiskeys, spirits and liqueurs while learning all about distillation, small-batch spirits and more. Added bonus: You’ll leave the Ravenswood booze factory with a nice little afternoon buzz.
Don’t stop: Bang Bang Pie & Biscuits | 4947 N. Damen Ave. 773-530-9020
Looks like you need something to soak up all those whiskey samples. Head just around the corner to Chicago staple Bang Bang Pie & Biscuits for a treat. Indulgent pot pies are shareable, or opt to chow down on your own biscuit creation. Don’t forget to save room for a slice of pie. If available, key lime never fails to impress.
Spanish food, then a speakeasy
Main attraction: Black Bull | 1721 W. Division St. 773-227-8600
Impress your date with an authentic Spanish meal at Black Bull — and by authentic, we mean executive chef Marcos Campos himself hails from Spain. Try the braised lamb shoulder with wine sauce, black garlic mashed potatoes, slow-cooked baby carrots and hummus and don’t skip out on trying a Spanish-style gin and tonic like the Sota with blackberries and basil. If you start to drift into a lazy food coma, don’t sweat it — your second destination is closer than you think.
Don’t stop: Bordel | 1721 W. Division St. 773-227-8600
Head to the second floor of Black Bull to enter Parisian and prohibition era-inspired speakeasy, Bordel. The velvet accents and dim lighting make for a cozy end to the date. The bar features a variety of entertainment during the week, including live music, burlesque and cabaret. Save room for “dessert” — the bananas foster old fashioned with rum, cinnamon, maple and walnut bitters will be calling your name.
Theater, then contemporary American fare
Main attraction: Royal George Theatre | 1641 N. Halsted St. 312-988-9000
Just looking to relax? Catch a show at the Royal George Theatre. Located conveniently off the North/Clybourn Red Line stop in Lincoln Park, it’s the perfect spot to watch an afternoon or evening performance with your family, friends or bae. The four-theater complex boasts four distinct stages, each offering a diverse array of theatrical events. If a pair of “Hamilton” tickets is still out of your budget, a production at the Royal George is sure to scratch your theater itch without breaking the bank.
Don’t stop: Boka | 1729 N. Halsted St. 312-337-6070
On the same block as the theater, you’ll find Boka, one of Food & Dining critic Phil Vettel’s Top 50 Restaurants in Chicago. Chef Lee Wolen brings an exciting menu to a restaurant that’s been a Chicago mainstay for more than a decade. While the ingredients he uses are familiar, the execution is beautifully complex. Don’t overlook Meg Galus’ imaginative pastries. Cocktails are first-rate, too, and an eye-candy dining room and flawless service don’t hurt, either.
View our full Chicago date night guide “
Sultry dance class, then Jamaican cuisine
Main attraction: Kizomba class at The Silver Room | 1506 E. 53rd St. 773-947-0024
The first time you watch a couple dance Kizomba, you might feel like a voyeur witnessing a private intimate moment — the Angolan dance is known for its slow, rolling hips and gyrations, so it’s perfect for a date when you’re already comfortable with your partner and want to turn up the heat. The Hyde Park store, art gallery and event space hosts lessons every Tuesday from 7-8 p.m., so bring your dance shoes and get ready to learn some new sexy moves.
Don’t stop: Ja’ Grill | 1510 E. Harper Court 773-752-5375
Take a short walk over to Ja’ Grill to satiate the appetite you just worked up. Try a couple patties filled with seasoned beef, curry chicken or veggies, then the signature jerk chicken with rice and peas, plantains, cabbage and carrots and Jamaican hard dough bread or the vegetarian Ital stew with callaloo, butter beans, carrots, onions, mixed vegetables and coconut cream. Wash it all down with the Ja’ Rum Punch with white, dark and coconut rums and tropical juices.
Ice skating, then hot chocolate
Main attraction: Maggie Daley Skating Ribbon | 337 E. Randolph St. 312-552-3000
The Maggie Daley Skating Ribbon is open all throughout winter for ice skating, and the classic activity feels especially enjoyable in view of the Chicago skyline. Grab a date — or a friend — and either bring your own skates at no charge, or rent skates at the park ($12 skate rental weekdays, $14 weekends). Once you’ve skated yourself exhausted or you’re ready to warm up, it’s time to head to your next destination.
Don’t stop: Goddess and the Baker | 33 S. Wabash Ave. 312-877-5176
After ice skating in chilly Chicago weather, you’ll be ready to warm up with a mug of hot chocolate. Goddess and the Baker — just a couple blocks from Maggie Daley Park — serves up rich hot chocolate in addition to an extensive menu of other specialty drinks. Try the Hot Mama Elixir with “liquid chocolate,” chipotle, cayenne and cinnamon for a drink with a kick or the Goddess Gringo Horchata for something more mild.
Comedy, then craft beer
Main attraction: The Second City | 1616 N. Wells St. 312-337-3992
They say laughter is the best medicine, so have a couple chuckles at The Second City. This club is a Chicago staple when it comes to comedy, putting on live shows every night. Comics perform a variety of sketch and improv comedy in a number of theaters. Shows start at 4 p.m., 7 p.m., 8 p.m. and 11 p.m. depending on the day.
Don’t stop: The Vig Chicago | 1527 N. Wells St. 312-982-2186
The Vig, located just a block south of The Second City, is the perfect spot to pop in for a beer and appetizer before or after a show. The loft-like sports bar, equipped with large TVs, serves up gastropub eats (think lobster deviled eggs, salmon BLTs and baby back ribs) and weekend brunch. With an extensive craft beer, wine, cocktail and spirit list, you’re sure to find something that quenches your thirst.
Ramen, then disco
Main attraction: Slurping Turtle | 116 W. Hubbard St. 312-464-0466
How could you go wrong with a late dinner at Slurping Turtle? This River North spot is the perfect place to get your hands on some delicious ramen, stir fry or sushi. You can start your meal with some fried Brussels sprouts, bao or duck fat fried chicken. Or, if you’re not in a snacking mood, go straight for an entree like the Spicy Miso Tonkotsu, complete with chicken, buttered corn, bamboo shoots, wood ear mushrooms and scallions. Don’t forget to take a peek at the dessert menu before you head out. You know, just in case.
Don’t stop: Celeste/Disco | 111 W. Hubbard St. 312-828-9000
After dinner, jet across the street to Celeste, a sophisticated multilevel hotspot that’s perfect for a late-night cocktail or snack. When you’re done with your drinks, head on up to Disco where the LED-lit floor and disco balls may just keep you dancing until the early morning hours. Pack in the fun of two completely different spaces without needing to step outside.
Chinese-American Museum, then Chinese food
Main attraction: Chinese-American Museum of Chicago | 238 W. 23rd St. 312-949-1000
Looking for an educational date night away from Museum Campus? Plan a visit to the Chinese-American Museum of Chicago in Chinatown. The “Great Wall to Great Lakes: Chinese Immigration to the Midwest,” a permanent exhibit at the museum, tells the stories of immigrant journeys from China to the Chicago area and elsewhere in the Midwest. “The Way We Wore: Celebrating Chinese Fashion Heritage” immerses guests in Chinese-American cultural life through exploration of Chinese fashion. Garments and accessories on display date back to the 19th century.
Don’t stop: Lao Sze Chuan | 2172 S. Archer Ave. 312-326-5040
Chicago’s Chinatown is full of great places to eat, but if you’re new to the neighborhood dining scene, Lao Sze Chuan is the place to start exploring. Since opening in 1998, Lao Sze Chuan has been a staple of Chinatown and it’s one of the best spots in the neighborhood. Try the pork potstickers to start, and the chef’s special dry chili chicken for the main course. The hot pot option is a great build-it-yourself way to try multiple things on the menu. The base broth for the hot pot is $10, with added charges for each meat, vegetable, seafood and noodle addition.
Sushi, then burlesque
Main attraction: Agami Sushi | 4712 N. Broadway 773-506-1845
First up is Agami Sushi for a quick bite. This chic Uptown sushi joint dishes up classic and specialty rolls as well as cocktails. Pay homage with the Chicago Bulls roll with spicy blue crab, baked scallops, grilled tiger shrimp, guacamole, pico de gallo and golden aioli. The menu is rounded out with a robust selection of salads, ramen, appetizers and buns.
Don’t stop: Kiss Kiss Cabaret at Uptown Underground | 4707 N. Broadway Ave. 773-867-1946
Next, heat up your night with a steamy striptease courtesy of Kiss Kiss Cabaret. Enjoy a vaudeville-inspired burlesque variety show, offering a mix of music, magic, comedy and the Kiss Kiss Coquettes. This weekly comedy and burlesque cabaret plays Friday and Saturday nights at Uptown Underground. The explosion of entertainment is suggested for guests ages 18 and up.
