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16 Chicago Winter Date Ideas

16 Chicago Winter Date Ideas

Welp. It’s officially February!!

Right now is about the time the winter blues really start to settle in–at least here in the midwest. Chicagoans know we’ve got at least two more months of cold ahead of us. (EEP!) But hey, that’s not such a bad thing.

Winter is actually our favorite time of the year for date nights. There’s a lot less hustle and bustle going on in the dead of winter, which means a lot of extra quality time! Plus, there’s something so romantic about a cozy date night that can’t really be replicated any other time of the year–don’t you think?

That being said, many of you guys have requested some date night ideas to get you through the final stretch of winter, so today, I’m sharing some thought starters based on our favorite things to do, as well as some places that are still on our list!

16 Chicago Winter Date Ideas

Art Institute + Chicago Athletic Association

A day at the Art Institute is one of my absolute favorites. (Tip: If you plan to go there more than once a year with a guest, definitely get a membership! Totally worth it, and you get to skip all the lines, too!)

There didn’t used to be much down by the Art Institute aside from chain restaurants, tourist traps, and Starbucks–but when the Chicago Athletic Association got revamped, that all changed–it has so many fun restaurants and bars! Cindy’s Rooftop is fun for cocktails and has one of my favorite views of the city. The Game Room has tons of fun games, and if you walk through the Game Room you’ll find Cherry Circle Room–which is gorgeous––grab a drink at the beautiful bar or make a reservation for dinner.

Tacos in Pilsen + Thalia Hall

I say “tacos in Pilsen” because there are quite a few amazing restaurants to choose from here! You will hear differing opinions on the best tacos in the neighborhood (Time Out has a great roundup!) but our favorite that we’ve tried so far is Los Comales. It’s a zero-frills spot with some of the most authentic tacos in the city-get the steak tacos, you won’t regret it! And make sure to take advantage of their homemade hot sauces and pickled veggies on the table!

After, head to one of my personal favorite places in the city–Thalia Hall. While I’ve never been to an actual concert at Thalia Hall, we have frequented all three of its bars–Dusek’s, Punch House, and the Tack Room. All are totally different vibes, and it’s so fun to make your way to all three of them throughout the night! Punch House is definitely my favorite–it’s a super funky 70’s vibe with tons of different boozy punches on tap!

Dinner in West Loop + Curling at Kaiser Tiger

So, when I got the idea of this post, I was working at the kitchen counter, as I often do. Neal had just gotten back from the gym, so I ran back to our bedroom to get his take. I opened our bathroom door and yelled through the steam of the shower, “Babe! I’m writing a post on Chicago winter date ideas. Do you have any?!”

He was silent for a few moments. (He does this thing where he thinks about what he’s going to say before he answers for what feels like hours, so you often don’t know if he’s got selective hearing, blatantly ignoring you, or deep in thought.)


(…I’m sorry, WHAT?! ????)

He meant Kaiser Tiger, one of our old hangouts when we lived in the West Loop. It’s was one of our favorite places to go in the summer due to their big outdoor space, but in the winter, they transform the patio into curling rinks! Such a fun out of the box date activity, right?

You can definitely eat at Kaiser Tiger, which has good bar food, but if you’re in the mood for something else, we’d recommend hitting up Gus’s for fried chicken. It’s a great best combination of a neighborhood takeout place and a trendy west-loop bar.” Casual, fun, trendy, but not too trendy. It’s the goldilocks of fried chicken.

Another great option nearby? Gyu Kaku Japanese BBQ. It’s so fun for a date or for a group–they have grills on each table and

The long and short of it: Go for the hot chicken, order a sweet tea cocktail, and you’ve got yourself a great meal.

Pizza at Paulie Gee’s + Beer at Revolution Brewing

Paulie Gee’s first made a name for itself in Brooklyn. We were visiting our friends, Matt and Erin in NYC the first time I tried this amazing, unique pizza. It is so, so good. A year later, when they opened in Chicago, Matt and Erin happened to be in town, and we decided we had to jump over to Logan Square to see if it was as good as the original. (It was!)

When you go, you MUST order the “Romaine Calm, All is Well” salad and the “Hellboy” pizza. (Seriously, don’t mess this up. If you order anything else I will be mad at you.) The Hellboy pizza is served with “hot honey” drizzled on top. You’ve never tasted anything so good!

After, stop at Revolution Brewing for a couple beers. Their IPA is Neal’s favorite, and I like the Bottom Up Wit. The brewery has a really cool vibe, and is perfect for a casual date night. Both Paulie Gee’s and Revolution are right in the heart of Logan Square, which has tons of other fun and cool bars–perfect for bar-hopping.

Fondue dinner at Gejas

We just went to Gejas recently (I hadn’t been in years) but it’s the perfect balance between a funky, kitschy experience and a romantic date night–it’s a Lincoln Park staple and if you don’t have a good time here, well, I think you just hate fun. ?

Fondue makes for a great interactive date experience, and the restaurant setting is funky, dark and cozy. Get the pre-fixe meal that includes a cheese fondue starter, meat and veggie fondue main, and chocolate fondue dessert! This is also a fun activity for groups as well.

I recommend going for a walk around Lincoln Park beforehand–walk through the Lincoln Park zoo (it’s free!), or grab a drink before or after at Gemini. (One of our favorite Lincoln Park restaurants!)

Games at Punchbowl Social

A casual and playful night (ideal for a first date especially) would be a visit to Punchbowl, which is basically a cool adult playground and has everything from shuffleboard to bocce to bowling to ping pong, foosball, giant Jenga, vintage arcade games and more.

There are so many places to grab dinner before or after in the West Loop, but I really love Bar Siena, which is one of my favorite casual spots–it’s one of Fabio Viviani’s restaurants and everything there is so good! Most of the plates are shareable so it’s fun to order a bunch of things so you get to try a little bit of everything!

Another favorite option nearby: Duck Duck Goat–which is Stephanie Izard’s Hot Chinese restaurant––just order whatever your server tells you, and it will be lights out. 

Best of the Gold Coast:

Gold Coast is one of our favorite areas to hang out in (outside of Wicker Park) and our go-to’s are always Le Colonial and Brasserie at the Waldorf! (We got engaged in the Waldorf’s courtyard!) Dublin’s is also our favorite Dive Bar! They’re open late night, 365 a year! Tavern on Rush, Hugo’s Frog Bar and Luxe Bar are also classics, especially for lunch if you’re doing a daytime date!

Ping Pong bar:

There’s a ping pong bar downtown called AceBounce that is fun to visit for a date or with a group! If you’re sick of just “going to bars”––try this one! It gives you something to do that isn’t just drinking! 

See a play at Steppenwolf

This itinerary is at the top of our list––I cannot believe we’ve never seen a play at the Steppenwolf! It’s one of Chicago’s most famous theatres and there are always several productions to choose from! Boka (same restaurant group as Alinea) is just down the street, making it the perfect destination for a post-theatre late night dinner. Tip: Steppenwolf has a really cute bar/coffee shop attached called Front Bar. Plan to get there early for a drink before the show!

Comedy show:

If a play isn’t your thing, another alternative is to see a show at the famous Second City or Zanies, which is a quick 5-minute drive away! Second City is more famous and you have more variety to choose from in terms of shows, but Zanie’s is my favorite––it’s a super cozy throwback club vibe with great service and good drinks! IO comedy theatre also opened a new nearby location which is supposed to be AWESOME but we haven’t made it there yet!

Broadway Show and dinner at BLVD: 

Chicago has so many FANTASTIC Broadway shows that are always changing and never disappoint. The restaurants in the theatre district though…can be quite disappointing. What I’d recommend instead, is going to BLVD! The location also makes it perfect to zip down Lake Street to the Theatre District to catch a Broadway show! (This is what we did for my birthday and it was the best night!) It’s also a prime location for bar hopping in the West Loop!

It’s one of our favorite date night spots––the vibe is a swanky, old Hollywood supper club, and the menu is what I would describe as upscale American–it’s expertly curated and has something for everyone. I don’t say this lightly, but I think their steak can hold its own up against heavy hitters like Bavette’s and Boefhaus! Their Cacio e Pepe is also so good [not traditional, but delicious!] Also, I HATE seafood, and even I loved their clams!! (See proof above!)

Time Out Market:

I have yet to make it to the new Time Out Market in Chicago! However, I HAVE been to the one in Lisbon and it was so much fun, I am sure the Chicago version does not disappoint! It’s a trendy food hall full of counters serving up some amazing food from some of Chicago’s best chefs!

Head to some live music bars:

There are SO many great bars to catch live music In the city–California Clipper (a perfect place to head after dinner at one of our favorite restaurants–Boefhaus!) There’s also The Green Mill–which has been on our list FOREVER and we still haven’t made it yet. (It was one of Al Capone’s old hangouts, and even has a secret underground tunnel!) Kingston Mines is also amazing–especially late night–and a total riot. This is a great roundup of a lot more!

Make a trip to Eataly:

As you know, one of my FAVORITE places! Eataly has a variety of restaurants, bars, counters, awesome happy hour specials, and lots of fun events–like pasta making, wine tasting, guided market tour, and more! You could have happy hour here and then pick up supplies to make your own romantic dinner at home!

Martinis and Dinner at Club Lucky:

Okay this isn’t an out of the box date idea by any stretch of the imagination, but it’s our #1 go-to in the winter! There’s just something about it that is so fun, cozy, and neighborhoody! It’s been a staple in the neighborhood for a LONG time––and you can tell, by how packed with locals it is at all times! They have the best martinis, great service and great Italian food. We love sitting at the bar!

Head to the baths!

Have you been to Aire Ancient Baths? They are SO COOL and so fun. Definitely, something amazing to do on a cold, rainy or snowy day. It’s fun, different, AND insanely relaxing. You won’t want to leave! You can also tack on a massage if you’d like!

Hope this list gives you some new Chicago date night ideas!

P.S. Want more Chicago reccos? Check out my favorite Chicago coffee shops, and my anti-tourist Chicago activity guide