Because it’s that time of the year again––whether you’ve lived here for years or you’re planning your first winter visit to the Windy City––we could all use a few new ideas for winter activities, right? I wanted to refresh this post that I wrote a couple years back, tackling the topic of: “What the heck can I do in Chicago when it’s freezing?!” and also, “HELP! What do I wear when it’s so cold?!”
I get this question 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!)
So, let’s jump in, shall we? Here are several things to do in Chicago in the winter, along with their google maps links so you can star your favorites–after, scroll to the bottom of the post for my advice on what to wear!!
Winter Activities in Chicago:
3 Arts Club & RH Chicago
Okay, this sounds strange to go hang out at a furniture store, but stick with me. It’s become SUCH a staple here in Chicago and I’ve never met a person who didn’t go gaga for it. The restaurant in Restoration Hardware is STUNNING. 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. Perfect for brunch, lunch, drinks or dinner! (It does get very busy though, so you may want to try and time it at an off-time or if you’ve got a week day!)
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 are always several amazing broadway musicals in the Theatre district, 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!) Zanies in Old Town is a personal favorite and is an OG comedy club. It’s on the main drag of Wells, so it’s great for bar hopping too!
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 one of the coolest neighborhoods in the city and houses most of Chicago’s hottest restaurants! If convenience is what you’re looking for, we always recommend The Ogden down the street from the UC for great bar food pre/post-game.
I love this museum. It’s very small and homey, and a little kitschy, but it’s really beautiful too! You’ll learn lots of cool things about the Windy City you can’t find anywhere else! Neal and I went on one of our first dates here!
Never been here personally, but this one is a GG reader favorite, especially when entertaining parents!
Explore and eat your way through Eataly
Eataly is basically my Disneyland. 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. You can also take lots of different classes, from wine tasting to Gnocchi making!
Cozy Up at RL (Ralph Lauren) on the Mag Mile
The COZIEST, swankiest, most beautiful spot for brunch or lunch. It’s right on Michigan Ave, so it’s really convenient for shopping! Even stop in for a drink or some dessert. One of my #1 recommendations for visitors–it’s always a hit.
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 a drink in their restaurant, it’s beautiful and overlooks the park!) I love their impressionist room. So many beauties!
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!
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.
Take a Gangster and Crime Tour
I’ve honestly ALWAYS wanted to do one of these and never have! Time Out Chicago did a great roundup of gangsters and crime tours and they all sound amazing! Many of them are bus tours so they’re ideal for cold weather!
Pretend its summer
If you can’t take winter anymore and have no escape, there are two places I recommend checking out.
First, is 90 Miles Cuban Cafe in Logan Square. It’s BYOB, so you can bring your own wine and they’ll make it into Sangria, or bring Rum and they’ll make it into Mojitos! Their food is phenomenal, and they enclose their patio (make sure to request a table out there) so you really do feel like it’s summer!
Second, is Summer House Santa Monica! You would SWEAR you’re in California. One of my favorite places for lunch and a perfect location for shopping in Lincoln Park!
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.
Tissue turtlenecks: 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 lots 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.
Another great option for your “bottom” layer on top is a button-down–my favorite are J.Crew’s chambray button-downs, because they look really cute under sweaters!
The holy grail fleece:
Dudley Stephens is my FAVORITE favorite top/sweater/thing to wear in the winter because it’s so incredibly warm. It’s a fleece (think like, North Face kind of fleece but warmer) and I think they are so cute and chic looking! They are so warm I don’t need to layer anything underneath them. It’s like wearing pajamas but not. They come in regular and tunic length–you can see my full review and ideas on how to style them in this post! They’re also a small, women-owned brand, made in the USA!
Second, layer a crewneck (I love Everlane’s Oversized Alpaca Crew, which comes in a bunch of colors!) or cardigan sweater over the top. If you’d rather go with a turtleneck top layer, that’s cool too–but you may want to go with a tee or something under just for an additional layer (just make sure it’s something decent so you can remove your sweater if you’re too hot inside!)
Third, pair with dark pants or jeans, because they look dressier for dinner and you won’t feel the need to change! Whenever I’m out and about (especially in a new city I’m visiting) I don’t like having to go back to the hotel to change for dinner, so dark jeans are a great thing to wear since they transition so well from day to night.
The warmest jeans EVER: Old Navy “Built-In Warm” jeans. They are INCREDIBLE. They are the only pair of pants I wore in Quebec City–I barely took them off! They’re lined with a fleecy material on the inside, so they’re like built-in long underwear but you don’t overheat inside, either. My favorite are the black Rockstar skinnies–30% off right now! They run TTS. (I wear a 0).
If you’re looking for regular jeans, I love Everlane’s authentic stretch skinnies, and for a jeans alternative, I also really love Spanx Velvet leggings because they’re super warm (warmer than normal leggings because they’re much thicker) but incredibly comfortable!
If you’re someone who gets REALLY cold, you can always get heattech tights to wear under your pants!
Do you need long underwear?
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!
(Again, heattech under layers might be worth looking into–but I guess I get warm enough with my warm coat while walking, and then I get too hot inside if I have TOO many layers on, so it’s really a personal decision!)
Do you REALLY need a Canada Goose coat?
Of course, if you’re visiting, check the weather beforehand. Chicago weather is notoriously all over the place. Some days it might be in the 40’s in January and in which case, you don’t need a puffer coat. But other times, it could be 10 degrees in March. It also depends on how much walking you plan to be doing (in which you’ll need warmer options), and if you plan to take public transportation (lots of waiting around freezing on train platforms with the wind whipping your face) or take Ubers (where you can virtually avoid being outside for more than 10 seconds). Use your best judgement.
If it’s going to be a cold spell (or you are a Chicago resident) you most definitely need a VERY warm coat–my life changed when I got a Canada Goose coat. (Previously I’d worn a North Face coat, which is warm, but not AS warm–no matter how cold it is outside I don’t shiver when I’m wearing it–which says A LOT.)
Here’s the thing though: Canada Goose parkas are VERY expensive. It’s honestly ridiculous (and no, I don’t like that it has real fur–I wish they made an option without it) but it lasts for a LONG time and I’ve never met ONE person who was like, “Oh, I wish I hadn’t bought that Canada Goose coat–it’s not worth the money.” Seriously. Said no one EVER.
The GREAT news though, is Lole’s Marybeth parka is an AMAZING, affordable Canada Goose alternative! It is as warm as Canada Goose–and is 700 fill power (the warmth measurement they use for down coats), which is actually WARMER than a Canada Goose! (Canada Goose is 650 fill power). PSA: The Marybeth is also on sale right now!!
However, the differences are in the details–these are very minor things but can be important based on your lifestyle:
The Marybeth coat is not AS form-fitting as Canada Goose, which has a very feminine shape. It’s still not “puffy” which I love, but if shape is the biggest factor to you after warmth, it’s just something to note.
Very nit-picky, but the pockets on the Marybeth coat aren’t as deep or as angled, so your hands don’t stay as warm AND I always fear my phone is going to fall out of them. When you zip it up all the way, there is more room in the neck of the Marybeth than on the Canada Goose, which is super snug at the neck–so it doesn’t let as much cold air in. (This is one of the reasons I chose the Canada Goose to bring to Quebec City with me over the Marybeth Coat.)
Additionally, the Canada Goose has straps inside that you loop your arms through that allow you to take your coat off and still have it strapped to you–almost like you’re wearing it as a backpack–(i.e. while standing in line to get coffee, riding the subway, etc–places you are DYING to take off your coat because it’s so stifling inside but can’t because it’s too much work to get it back on or you have your hands full).
BUT–those are very reasonable negotiables and may not justify several hundred more dollars for you. If budget is your main factor, I don’t think these nit-picks are going to be worth the $500 price difference–I definitely think the Marybeth is an excellent route to go!
On the flip side, if you do have the funds, and the above details are important to you, you are never going to be sorry you got the Canada Goose. There is no wrong choice here!
More fantastic, and less-expensive options:
Lole’s Katie coat or the Lole Nora coat–(both on sale right now!! Nora is pictured below)–not AS warm (I’d say suitable for temps down to low twenties, vs the above coats are good well into the negatives).
I would say these are a warmth equivalent to an average North Face puffer–but SOOO much cuter! I’d definitely opt for either of those over a North Face or Patagonia. (The Nora coat is new this year and has become a particular favorite of mine due to the pretty burgundy color and also how long it is!)
Boots (especially tall ones) are your friend!
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! (It doesn’t matter what kind, just SOMETHING. Unless they’re Blondo and come weatherproofed already.)
My favorite pairs are the Stuart Weitzman Lowlands (splurge) but Blondo’s OTK boots are the budget-friendly pair I recommend to EVERYONE. They are actually fully waterproof, so no suede protectant necessary–and they are so beautiful and no break-in is required! I have turned so many people onto these boots over the years––they are truly a godsend and are a stylish alternative to rain or snow boots!
Speaking of snow boots, you probably don’t need heavy duty Sorel type snow boots if you’re visiting for the weekend. (They’re bulky!) Anywhere you stay downtown is going to do a really good job with shoveling sidewalks, but you may want something like my fave cute Cole Haan boots–which are waterproof, warm, AND cute at the same time!
Hats, scarves, and gloves really make a difference:
Accessories go a LONG way in keeping you warm–I know it can be a drag wearing a hat, but buying a couple different neutral colors so they go with (and enhance) the outfit you’re wearing will make a huge difference. If you don’t make your accessories an afterthought, you won’t feel like a 5 year old ready to go out on the playground.
A cute plaid scarf in some neutral colors, and a cute beanie in black, white, and/or tan are really all you need to round out a cold weather wardrobe. I also recommend either cashmere lined leather gloves (like these that are also tech gloves!) or, if you really only care about warmth–puffer mittens because they keep your hands SO much warmer.
What to wear out at night in Chicago?
Another question I get a lot–what do you wear out? 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––that’s honestly what most people will be wearing! Things are just more casual here.
On the flip side, if you want to wear a dress and heels, that’s great too! You’ll fit right in wearing that as well. Honestly, nobody cares or notices stuff like that here, so don’t overthink it. 😂 Chicago isn’t the kind of place where people watch you when you walk in and pay attention to what you’re wearing!
In the winter, I usually go for jeans, a cute blouse or sweater, booties or boots, and a swipe of red lipstick–maybe a faux fur coat for fun! (I have TONS of outfit ideas you can peruse through here!)
Need more winter fashion guidance? Check out our Real Women Approved Post: 20+ Must-Have Essentials to Get You Through Winter!
What are YOUR favorite things to do in Chicago in the winter? Any layering tips that have worked especially well for you? Would love to hear them!