I hope these Chicago winter date night ideas will help you explore new things to do in Chicago. I've paired activities with nearby restaurants and bars and made sure to include a wide range of Chicago neighborhoods.
Chicago Winter Date Night Ideas:
Some of these date nights can be enjoyed any time of the year, while others involve ice skating or visiting special events.
The Balloon Museum and Dinner at void
Avondale
Did you know that Avondale was named as one of the coolest neighborhoods in the world? This date brings you to this neighborhood just north of Logan Square. The Balloon Museum features a series of 18 immersive inflatable art installations, including an absolutely massive ball pit. It's so unique and truly awe-inspiring. The museum is only in Chicago through the beginning of April. Book tickets online in advance.
void, a cozy neighborhood Italian restaurant, is about a 15-minute walk or a 5-minute drive from The Balloon Museum. The menu has fun takes on Italian classics, like fried chicken marsala and spaghetti uh-os. void is a great date night pick - it's dimly lit, quiet, and unpretentious.
Lost Language and Spacca Napoli
Ravenswood
Lost Language is a Finnish-style sauna in Ravenswood. Warm up in communal saunas and cool off in an outdoor cold pool. Lost Language was created as a social space, and the saunas fit 15 people each. The electric saunas are open daily, and the wood-fired saunas are fired up on weekends. Sauna sessions are 60-minutes and need to be booked in advance.
Spacca Napoli, undisputedly one of Chicago's best pizzerias, is right around the corner. Spacca Napoli serves Neapolitan-style pizzas with a menu that includes classics like Margherita, Funghi, and Prosciutto e Rucola, plus pizzas like the Pistacchio topped with mozzarella, pistachio cream, sausage, and basil. Reservations are accepted.
The Chicago International Puppet Theatre Festival
Various Locations
This annual theatre event takes place at theatres throughout the city from January 21 to February 1. The kid-friendly production, The Enormous Crocodile, which features large animal puppets that actors ride, wear, or hold, will be at the Studebaker Theatre in the Loop. The Sex Lives of Puppets, a comedic play for adults, will be at the Biograph in Lincoln Park. Dead as a Dodo, also at the Studebaker Theatre, has also caught my eye.
For shows at the Studebaker, nearby dining options include The Gage a chic gastropub on Michigan Avenue, Exchequer, and Mercat a la Plaxa. If you go to the Biograph (where John Dillinger was shot), you might want to check out The Gatsby, a speakeasy located above the Bourgeois Pig Cafe. Listen closely to the host, who will give you clues to the password required to enter the cocktail lounge.
Deep-Dish at Exchequer and Buddy Guy at Buddy Guy's Legends
The Loop
The most "Chicago" of my Chicago winter date night ideas involves eating deep-dish and then seeing one of the city's most famous blues musicians. The Exchequer is a restaurant and pub with tin ceilings, known for being one of the best places for Deep Dish Pizza.
Next, walk south a few blocks to Buddy Guy's Legends to see 89-year-old Buddy Guy's January residency. Watching him perform is the ultimate Chicago experience - I was lucky to see him years ago when he took the stage because the scheduled performer was stuck in traffic. Be prepared to follow the strict no-video policy. Book tickets in advance online.
Ice Skating at the Maggie Daley Ice Ribbon and dinner at Chicago Athletic Association
The Loop
Skating around the Maggie Daley Ice Skating Ribbon is so much more fun than skating in circles around a rink. I love the juxtaposition of skating through a nature path with the Chicago skyline behind you. Make a skating reservation online in advance, as capacity is limited. Sessions are two hours long, and skate rental is available.
The Chicago Athletic Association Hotel is just across Michigan Avenue from Maggie Daley Park. The Drawing Room, with its massive fireplace, is one of the coziest spots in the city. It is open to the public, and breakfast, afternoon, and evening menus are offered. Once you have warmed up, you might want to visit the Game Room with billiards, shuffleboard, chess, and checkers. The game room has a bar and serves pub food.
Elston Electric and a show at Salt Shed
West Town
Elston Electric is an arcade located in the old boiler room of the Morton Salt factory. It has a fun mix of retro and modern games - play Space Invaders, shoot up zombies, or try one of the many pinball machines. A full bar offers snacks like Italian Beef taquitos, as well as pizza and hot dogs.
If you want more of a meal, head to Goose Island's brewpub around the corner.
Winter shows inside at the Salt Shed include Jason Isbell and the 400 Unit, Rainbow Kitten Surprise, and the Dropkick Murphys. I love this venue - it's big enough to attract great bands, but small enough to feel intimate. Another plus is that it is easy to get to.
You can read more about Salt Shed here.
Dinner at Mercat a la Planxa and a Live in Concert Film with Chicago Philharmonic
The Loop
Mercat a la Planxa is a Spanish restaurant that should get more attention. Reservations are easy to get, and the food is consistently great. Sip sangria and snack on bacon-wrapped dates and patatas bravas before sharing the restaurant's speciality: grilled meats.
After an early dinner, walk over to The Auditorium, one of Chicago's grand old theatres, to catch one of Chicago Philharmonic film series performances. Titanic is being performed on February 13th and Indiana Jones and the Raiders of the Lost Ark is being performed on March 28th. I love the film series performances and go to at least one each year.
Want a nightcap? Visit Club X, a speakeasy behind the Exchequer.
Burgers at Little Bad Wolf and The Magic Lounge
Andersonville
Little Bad Wolf makes some of the best burgers in Chicago. Unfortunately, reservations are not accepted, so be prepared to wait for a table. While the burgers are the star of the menu, there are plenty of other options, including tacos, bao, and salads.
The Magic Lounge is a speakeasy-style magic lounge hidden behind the facade of a laundry mat. Magic Shows take place nightly at 7 pm. In addition, there are 10 pm shows on Fridays and Saturdays. While shows on the main stage require tickets, the Performance Bar opens nightly at 5 pm and does not require tickets. This is a fun place to have a drink and see a bit of magic.
Second City and drinks at Old Town Ale House
Old Town
My neighbor's show, Love is Improvised, inspired by the reality dating show Love Is Blind, is returning to Second City in February. I love Second City because there are multiple stages and there are always several shows to choose from. It's a foolproof date night - we go at least once a year.
Either before or after the show, visit one of Chicago's most iconic dive bars: Old Town Ale House. One of the few remaining cash-only bars in the city, Old Town Ale House is decorated with unique political portraits painted by the bar's owner.
MADE Chicago Workshop and Margie's Candies
Bucktown
MADE is a ceramics and woodworking studio that offers both workshops and classes. You can visit once, or turn this into a weekly date night by signing up for a class. MADE's classes include wheelthrowing, handbuilt pottery, and making drinkware sets. Workshops include making wood serving trays, decorative ceramic plates, and hand-built mugs.
Is it ever too cold for ice cream? Margie's Candies is an ice cream parlor and candy store that opened in 1921. It's reasonably priced, with most sundaes priced between $10 and $12, and portions are generous. Try a banana split, brownie à la mode, root beer float, or come up with your own creation. The decor takes you back in time, leather booths, a marble soda fountain, jukeboxes at every table, and original Tiffany lamps. The Beatles and Al Capone have patronized Margie's Candies. And, The Bear has filmed here. It's a slice of Chicago history with delicious ice cream.
AIRE Ancient Baths and Dinner at Perilla
West Town
AIRE is a bathhouse and spa located in a restored factory in West Town. Relax in thermal baths and saunas, or get a massage or spa treatment. My favorite part of the AIRE experience is the indoor/outdoor hot pool with a waterfall feature - we've been there when it's snowing, and it's magical.
After you are all warm and relaxed, head over to Perilla, it's just over half a mile away. Perilla is a Korean steakhouse, and there is something romantic about warming up next to the grill and feasting on grilled meats and vegetables. In addition to the grilled items, try the scallion pancake and the honey butter potatoes.
Of all the Chicago winter date night ideas shared here, this is the one my husband and I did most recently. This is a great date night - we came home feeling so zen.
Ice Skating at Midway Plaisance and Lunch or Dinner at Truth Be Told
Hyde Park
Midway Plaisance, a park located beside the University of Chicago campus in Hyde Park, is home to an ice rink in the winter. Open Skate requires registration and is free if you bring your own skates. Skate Rental is available for $7.
Grab lunch before skating or dinner after skating at Truth Be Told, a British gastropub inspired by the Cotswolds. The menu has British pub staples like Bangers and Mash, Pot Pies, and Fish & Chips. A Sunday Roast is offered during Brunch on Sundays.
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