One of my most requested topics as of late has been “what the heck can I do in Chicago when it’s freezing?!”–I get this from visitors and locals alike. The good news is that no matter what the weather, there is always PLENTY to do in Chicago! I actually got a lot of these recommendations from you guys back when I asked what kinds of things to do with my mom when she came into town for Thanksgiving! (That and, of course, I threw in quite a few of my favorites as well!)
Another related question that I’m typically asked, is what to WEAR in Chicago in the winter. I’m sharing some of my favorite tips at the bottom of the post!
So, let’s jump in, shall we? Here are 20 things to do in Chicago in the winter, along with their google maps links so you can star your favorites! 😉
Winter Activities in Chicago:
Explore the 3 Arts Club & RH Chicago
Okay, this is kind of insane, but I’ve never actually been to RH. I know, it’s crazy. It’s become SUCH a staple here in Chicago and I’ve never met a person who didn’t go gaga for it. You’re probably saying, “Wait, like, the furniture store?” Yes, it IS a furniture store, but it’s so much more. Just watch this video. It’s essentially a gorgeous restaurant and cafe, with a garden, terrace–every inch of it asking to be instagrammed. This is definitely on my list to take my mom!
Soho House (Their restaurant is called The Allis), The Drake, and the Peninsula all have very popular afternoon tea options. A great activity that doesn’t revolve around drinking, as so many other things in Chicago do, haha!
See a Play, Musical or Comedy Show
Chicago has SO many options to see plays and musicals! There is always an amazing broadway musical at the Cadillac Theatre, and Steppanwolfe always has an interesting play running! Chicago is also famous for its comedy scene and there are SO many options when it comes to comedy shows–Second City is a must, which is also a comedy school that churns out the top talent in the country, but there are so many great comedy clubs (here is a google maps listing so you can star away!)
Take in the view at one of Chicago’s Rooftop Bars and Restaurants
Chicago has so many rooftop bars–many of which are still a great spot to check out when it’s cold! There’s Cindy’s Rooftop, which is the rooftop restaurant at the Chicago Athletic Association hotel. Go for a drink before or after you check out the Bean and Millennium park. I also love The Robey’s rooftop, the Up Room (get there early to watch the sunset, it gets packed even on weekdays!) Both of these offer a view of the skyline you won’t see anywhere else! It’s also one of my favorite spots for brunch or coffee!
Whether you’re entertaining visitors or you’re the one visiting Chicago, make sure to get out of downtown, too! Tourist attractions are nice, but you’ll really fall in love with where the locals live. My two favorite shopping areas are in Wicker Park/Bucktown (a Western neighborhood–where I live!) and Lincoln Park (an Eastern neighborhood, by the lake!)
I know, technically this involves going OUTSIDE when it’s freezing in the winter months, but the shops in the following two neighborhoods (my faves) are super close together so you won’t have to be in the elements for too long before warming up!
In Lincoln Park, make sure to shop all along Armitage avenue (near the brown line Armitage stop!) and from there you can walk to Halsted street (go left on Halsted!)–both streets are lined with charming shops. When you get to the end of Halsted, take a stroll through Oz Park if the weather is nice enough!
Both of these neighborhoods also hold some of the best Chicago restaurants, so it’s easy to make a day out of exploring them! (Plus, they’re a quick Uber or bus ride from one to the other).
See a Chicago Blackhawks or Chicago Bulls game
I’m not the biggest sports fan in the world, but I love going to games at the United Center, where the Hawks and Bulls play! Truth: I go for the hot dogs. Who can blame me? Your husband will love it though 😜 Also, a plus: Hockey and Basketball are way easier to follow and more entertaining to watch than football 😉
The UC is also really close to the West Loop, which is known as “restaurant row” (a lot of Chicago’s hottest restaurants are in this neighborhood–two of our West Loop favorites are Girl and the Goat and BLVD).
I love this museum. It’s very small and homey, and it’s really beautiful too! You’ll learn lot’s of cool things about the Windy City!
Never been here personally, but this one is a GG reader favorite, especially when entertaining parents!
Explore and eat your way through Eataly
I’ve never met anyone who hated Eataly! What’s not to love? All foodies will go googly eyed over all of the fine Italian goods. If you’ve never heard of it, it’s basically a gigantic beautiful gourmet store full of the finest Italian goods you’ve ever seen, combined with a few different gourmet Italian restaurants and bars ALL IN ONE.
Brunch at RL (Ralph Lauren) on the Mag Mile
I can’t tell you how many recommendations saying this was a go-to place to bring visitors from out of town. It’s swanky, posh, and delicious. Plus, it’s right on Michigan Ave, so it’s really convenient for shopping!
Chicago’s Famous Museums
The Field Museum, Museum of Science and Industry, Shedd Aquarium and Art Institute are world famous for good reason! I absolutely adore the Art Institute (make sure to grab lunch in their restaurant, it’s beautiful and overlooks the park!) I love their impressionist room. So many beauties by Monet!
There are a lot of fun places to go ice skating in downtown Chicago and pretty much anywhere else around the city. If you’re in a popular neighborhood, there’s likely an ice skating rink somewhere nearby! There’s Millennium Park and Maggie Daley Park “skating ribbon”, there’s a rink at the Lincoln Park Zoo, and one at the Peninsula with beautiful skyline views! (Just make sure to bundle up!)
This is a must-do for kids. Kelly and Mitch love it!
This is around Christmastime but putting it in here if you happen to stumble upon it next year. I would usually tell most people to avoid Navy Pier like the plague but this actually looks like a cool family fun activity!
Another GG reader must-do! I haven’t been yet, but can’t wait to check it out. Rumored to be especially great during the holidays, this is an old-school staple in the city.
The Game Room at Chicago Athletic Association
The same hotel that houses one of my favorite rooftop restaurants! The Game Room is one of the few “game” spots in the city that both serve alcohol AND allow kids during the day. And no, by “games” I don’t mean arcade or video games (thankfully). It’s a super swanky cocktail lounge that has billiards, bocce, shuffleboard, foosball, chess and checkers tables, and more. It’s also open until 3am on weekends! Whether you’re on a date or with your kids, this is a spot everyone will think is awesome.
Another gem from Mitch and Kelly. This is a bookstore that doubles as a bar/cafe–they have fun board games, too! They have a “laptop free” rule that encourages everyone to be offline and in the moment, which is a nice breath of fresh air!
Beer (or Kombucha! Or Cold brew!) and board games at Tapster
This Wicker Park bar has TONS of beer on tap–32 beer, 8 wine taps, 4 Kombucha taps, 4 craft soda taps and 2 cold brew taps–to be exact. You also pour them yourself, so that’s part of the fun! They have board games you can drag out and play!
Frank Lloyd Wright Tour in Oak Park
Again, I had never heard of this one either! (You guys really do give me the best ideas!) Did you know that Chicago’s suburb of Oak Park boasts more FLW homes than anywhere else in the world? The FLW trust organization offers a 3 hour tour, which is apparently phenomenal.
How to dress in Chicago Winter:
Okay, so we’ve covered what things to do in Chicago in the winter…but what do you wear? This is a very common question I get from visitors AND locals. How do you dress cute when it’s so darn cold?! 😭
Here are a couple quick tips:
Lot’s of layers:
The thing about Chicago is that it’s deathly cold outside, but when you get inside, you’re sweating. The key to navigating this temperature rollercoaster is to dress in layers–with a thin layer on the bottom, which seems counter-intuitive, but stick with me.
First, if I know I’m going to be out and about all day, I usually gravitate toward J.Crew’s tissue turtlenecks. I own them in lot’s of colors and they are my #1 winter staple. These are great because they add warmth but they look really adorable on their own, so when you strip off all your other layers, you still look put together. I also just ordered this long-sleeve tee in black and white stripe and black, which are reversible–so you can wear them as a crewneck OR v-neck which is so amazing. They’re lightweight (but not TOO) thin, so they make the perfect under-layer! Another great option for your “bottom” layer is a button-down–my favorite are J.Crew’s chambray button-downs, because they look really cute under sweaters!
Second, layer a crewneck or cardigan sweater over the top. My favorite color for this second “sweater layer” is camel, because it looks lovely on every skin tone and it instantly makes you look way more chic and put together. I’ve been wearing this cardigan (pictured above) non-stop–it’s SO cozy and warm (runs big, size down at least one size!)
Third, pair with dark pants or jeans, because they look dressier for dinner and you won’t feel the need to change! (My new favorite pair is from Abercrombie, if you can believe it!)
Another common question: Do you need long underwear in the winter in Chicago? Personally, I would say no unless you’re planning an all-day wilderness hike. Kelly would say 100% yes and she wears long underwear daily. Use your best judgement! 😂
A nice pair of jeans and flat boots are acceptable just about everywhere:
The best part about Chicago is that nobody is ever going to turn you away for wearing jeans and flat boots, even in a super nice restaurant. Things are just more casual here. On the flip side, if you want to get dressed up and wear a dress and heels, you won’t feel out of place either! But as a general rule, don’t feel like you have to wear heels anywhere.
Quick tip: The taller your boots are, the warmer you will be. This is never something I realized until I got a pair of OTK boots and realized they add the warmth equivalent of about three pairs of pants, so if you have them, definitely wear them as often as possible. BUT. Please, please, for me, and yourself–make sure you spray them with LOTS of suede protectant beforehand! My favorite pairs are the Stuart Weitzman Lowlands (splurge) Blondo Olivia boots (budget-friendly!) and the Splendid Danise knee-high boots (great price on these too, and they have a small chunky heel which makes them a little bit dressier but still comfy enough to walk around in!)
Hats, scarves, and gloves really make a difference:
They go a LONG way in keeping you warm–and make sure they match the rest of your outfit, too, or else you’ll feel like a 5 year old getting ready to go out on the playground 😂 I speak from experience. Seriously, buying a couple different neutral colors will get you a long way and make you love your outfit SO much more!
What are YOUR favorite things to do in Chicago in the winter?