5 Chicago Winter Date Ideas

 

The view from Cindy’s Rooftop. Photo by Kelly.

Welp. We’re officially nearing the end of January!

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, Neal and I put together a list of five fun Chicago winter date ideas, comprised of our favorite spots in the city. Whether you’re local, or planning to visit, you’ll definitely want to make room in your itinerary.

Fried Chicken at Gus’s + 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 minutes. (He does this thing where he thinks about what he’s going to say before he answers, so you often don’t know if he’s got selective hearing, blatantly ignoring you, or deep in thought.)

Then he yells back, “Oh! Yeah! What about curling at the sausage place?!”

(…I’m sorry, what? Did he mean Kaiser Tiger?)

Yes. He meant Kaiser Tiger. One of our old hangouts when we lived in the West Loop. It’s one of our favorite places to go in the summer due to their huge outdoor space, but this winter, they transformed 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 some fried chicken. Neal describes it best. He says,”Gus’s is “the 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.

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

Michigan Ave stroll + dinner at Allium

Allium is one of our very favorite spots downtown. Personally, I think it’s one of the most romantic, swanky places in the city–and is a bit of a hidden gem. You won’t usually see it listed among Chicago’s trendiest restaurants, or on many “hot lists” but it’s classic, old-school, and has amazing service. They also have a fireplace, which makes especially enticing on a winter day.

It’s located in the Four Seasons, which is right off of Michigan Avenue. Extra points if you save this date for a day where there’s snow in the forecast. There’s really no prettier sight than Michigan Ave covered in snow. Grab a coffee or hot chocolate, and walk up and down the magnificent mile for some window-shopping, making Allium your end point.

For post-dinner drinks, head across the way to Drumbar, which also happens to be incredibly swanky with big chesterfield couches, dark, moody lighting, and an impressive cocktail menu.

Tacos in Pilsen+drinks at 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 favorites 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!

Afterwords, 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!

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!

Afterwords, 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.

Cindy’s Rooftop + Art Institute

Cindy’s (I wrote a whole post on it here) and the Art Institute really make the perfect match. 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. Now it’s home to one of my favorite downtown spots, Cindy’s rooftop. It’s a perfect place to begin a weekend date–brunch with a cocktails, followed by a visit to the Art Institute. (It also happens to be one of the prettiest views of the city!)

When we first started dating, we skipped work one day and decided to go to the Art Institute, and it’s still one of my favorite memories to look back on 🙂

Have you tried any of these spots? What are your favorites? 

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