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25 Things to do in Chicago in the Winter (And What to Wear When It’s Freezing!)

Feb 3, 2022

Things to do in Chicago in the Winter

Above at the Art Institute: similar coat, similar skirt, Uniqlo Heattech tights, Dudley Stephens turtleneck, old loafers

What perfect timing to refresh this post! Chicago got SEVERAL inches of snow yesterday, and I thought “TODAY IS THE DAY” to give this much-requested blog post an update.

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? Two questions I frequently receive this time of year (from visitors and locals alike): “What the heck can I do in Chicago when it’s freezing?!” and also, “HELP! What do I wear when it’s so cold?!”

The good news is that no matter what the weather, there is always PLENTY to do in Chicago! Many of these recommendations came from you all via Instagram, and of course, I threw in 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.

(Also, keep in mind, you’ll want to double check hours/etc as things may change due to pandemic restrictions. Additionally, at the time this is published, Chicago does require masks as well as proof of vaccination status for most indoor activities–restaurants, bars, museums, etc, so make sure you have a photo of your vaccine card on you along with your ID. Please adhere to these best practices to keep yourself and others around you safe!) 

At the bottom of this post, you’ll find my reccos on what to wear in Chicago in the winter, no matter where you’re going!

Things to do in Chicago in the Winter - afternoon tea

Above: Tea at the Drake is such a fun experience! 

Winter Activities in Chicago:

3 Arts Club & RH Chicago

One of the most instagrammable spots in the city! I know it 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 weekday!)

Afternoon Tea 

The Drake, and the Peninsula have very popular afternoon tea options that are so much fun for all ages! Also 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 showsSecond 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 as many are insulated! 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! Check out this roundup for a list of Chicago rooftop restaurants that are open this winter!

Neighborhood shopping

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 the neighborhoods. 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 typically send visitors here because you have a ton to do in a small area.

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!

If you venture to Wicker Park/Bucktown, shop around the 6 corners intersection of Damen, North and Milwaukee! There are lots of boutiques along Milwaukee and Damen. (See my favorites in this post!)

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

Always an authentic Chicago experience! Both teams play at the United Center. Truth: I go for the hot dogs, but if you are a fan or have a sports-loving partner, they will love it. 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–so even if you’re not into sports, perhaps a great dinner and/or drinks pre or post game could be a great compromise!

Chicago History Museum 

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!

Cooking Classes

There are so many fun cooking class options in Chicago. Sur La Table, Cooking Fools, and The Chopping Block come to mind, just to name a few. The cost of admission includes your meal, too 🙂

Garfield Park Conservatory 

Never been here personally, but this one is a GG reader favorite, especially when entertaining parents or kids!

Explore and eat your way through Eataly 

(Note I haven’t been here since the pandemic started, so I’m not totally sure it’s all the same, but I’m sure it’s still worth checking out!) 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. Make reservations because it can be hard to get a table!

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! And the Museum of Contemporary Art is free for Chicago residents on Tuesdays!

Ice Skating

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! Depending on the time of year, 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!)

Go For a Winter Hike

There are many forest preserves around Chicago that are beautiful for winter hikes! Check out Bunker Hill Forest and LaBagh Woods for a gorgeous view along the river!

Warm-Up at a New Bar

No one has a bar scene quite like Chicago! From cozy bars with a fireplace to cozy basement dive bars to activity-based bars, there’s something for everyone! Check out a new neighborhood when you need to switch things up!

Experience the City By Snowshoe

I had no idea this was even a thing, but thanks to one of you, now we all know! If there’s plenty of snow on the ground, you can rent snowshoes and head to the arboretum or Northerly Island for a fun cold-weather activity.

AIRE Ancient Baths

Enjoy some R&R and warm up at AIRE Ancient Baths with a thermal soak and a massage! Book one with your partner or go with a group of girlfriends!

Check out a Candle-Making Bar

Stop by Aura Candle Bar for a fun activity with girlfriends or family and make something that will keep you warm and cozy until spring! The candle-making process takes about 30 minutes- would make a great activity for visitors too!

Chicago Children’s Museum

This is a must-do for kids. Kelly and Mitch are there frequently. It’s located on Navy Pier, which has gone through a major transformation in recent years and has lots for parents too–a beer garden, several restaurants, etc. It’s easy to make a day of it!

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.  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.

Kibbitznest Books & Brews 

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 screen free rule that encourages everyone to be offline and in the moment, which is a nice breath of fresh air! (Note: Not the best place for littles though, as they’re not allowed to be on iPads or phones. Not cocomelon friendly!)

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.

Try Curling

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:

Things to do in Chicago in the Winter + How to dress in Chicago Winter

Dudley Stephens Fleece, Commando leggings, Blondo waterproof suede all-weather boots

The thing about Chicago is that it can be deathly cold outside, but when you get inside, you’re sweating. The key to navigating this temperature rollercoaster is to dress in layers so you can remove them if it’s too hot once you get inside!

Base layers: 

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. They’re a great base layer–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.

Uniqulo’s Heat Tech items are also really thin and perfect for layering, but keep you super warm. You guys raved about them in our Real Women Approved: Must Have Winter Essentials post!

Bodysuits: Similar to a tissue turtleneck,  a thin bodysuit like this one also makes a great layer to wear underneath say, a jacket or another sweater, or all on its own (a black turtleneck bodysuit is one of my most-worn “going out” items in the winter!)

The warmest fleeces: Dudley Stephens is my FAVORITE favorite top/sweater/thing to wear in the winter because it’s so incredibly warm. It’s a thick fleece (not quite a sweater or a sweatshirt or a top–it’s kind of all of the above?) They aren’t just practical. But I think their collars make them very chic, too! They are so warm I don’t need to layer anything underneath them. 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! Note: These are on the pricier side, definitely not something you need to buy for a cold weekend visit, but definitely worth the investment IMO if you live somewhere where the temps are often arctic.

Top layers: 

You can also consider a crewneck or cardigan sweater over the top of a cute, thin base-layer turtleneck (i.e. tissue turtleneck). 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!)

Bottoms: 

Third, your most versatile bottoms are going to be a pair with dark pants or jeans, because they’re easiest to dress up when necessary, making them ideal for day or night.

The warmest jeans EVER: Old Navy “Built-In Warm” jeans. They are INCREDIBLE. On the coldest days, they’re the only pants I wear. 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– on sale right now! I think they run a bit roomy, so if you’re usually in between sizes you could consider going down a size if you’d like them to be tight/snug. Or order your regular size if you want a bit of room.

If you’re someone who gets REALLY cold, you can always get heattech leggings (or other fleece-lined leggings/long underwear) to wear under your pants!

Do you need long underwear? 

Do you need long underwear in the winter in Chicago? This is a question I often get from visitors. My advice: Check the weather and pay attention to the wind chill. (If it’s under 20 degrees, I’d say bringing long underwear just in case won’t hurt!) As a rule though, unless you’re going to be walking around for long periods of time, I would say you probably don’t need it. (I never wear it). I would say get yourself a pair of the Old Navy warm jeans and you’ll be set.

(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!)

Things to do in Chicago in the Winter

Above: The warmest $159 parka (order your normal size, I have small)Sorel Tofino boots (budget-friendly dupes here!), Black Old Navy Fleece-Lined Jeans (see above for sizing notes), Dudley Stephens Fleece turtleneck (reviewed/sizing here), Similar hat

What kind of coat do you need for Chicago winter? 

Of course, like I said, if you’re visiting, check the weather beforehand. Chicago weather is notoriously all over the place. You can get negative wind chills or 40 degrees in January, you could get a blizzard or a 60 degree day 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 judgment.

For weather around 30 degrees or above, I think you could easily get away with a warm wool coat (highly recommend J.Crew’s cocoon coat!

It’s been a staple in my wardrobe for years now.) For temps below, you’ll likely want a parka if you plan to be walking/outside for any stretch of time!

If I were investing in a down winter parka for living in Chicago now (the coats I have and have frequently recommended are no longer in stock!) I would say to look for something that’s a very high fill-power rating (which is the warmth measurement for down coats). You’ll want a coat that’s ideally at least 550 or 600 fill-power. The zipper should have a storm flap covering (to keep wind out). You definitely will want it to have ribbing around the sleeves (also to keep cold air out) and fleece lined pockets. A hood isn’t something I love aesthetically but practicality-wise, you’ll definitely want it. Something that checks all these boxes is this Marmot coat, for example! Another option would be this North Face parka!

Now, a very honorable mention, if you want something more budget friendly: “THE Amazon coat.”

I bought it this year to wear when wearing June (as it expands at the sides so it’s great for baby wearing!) It’s very inexpensive for a winter coat and will only set you back $159–to my absolute shock, it is almost as warm (if not just as warm?) as my down parkas that cost HUNDREDS and hundreds of dollars! It doesn’t have ALL the thoughtful features that I mentioned above, but it’s pretty darn close.

It also comes with added versatility–like I mentioned, it expands at the sides, so it’s great for zipping up over June when I’m wearing her in her carrier (and also great for a baby bump). I wear it ALL the time, even on some of the coldest days we’ve had this winter, and it’s kept me really warm. I really don’t think you can beat it for the price!

My biggest knock is that it’s not waterproof, so depending on how much you’re outside, you may want a waterproof option, but maybe not! I think you could totally get by with just this coat alone during the winter.

For more tips on layering, see my posts5 Tips for Warm Winter Layering and How to Look Chic (Not Bulky) in Winter Layers!

Things to do in Chicago in the Winter

An outfit formula I wear out a lot in the Chicago winter months: Black bodysuit, Black Old Navy Fleece-Lined Jeans, Black Blondo boots, Sezane belt. See more winter date night outfits here

water-resistant lug sole Chelsea boots | Things to do in Chicago in the Winter

These water-resistant lug sole Chelsea boots are a pair I wear often in Chicago winters! (Come in more colors too!) 

Boots boots boots!!

What shoes you can leave at home (for visitors):

If you’re visiting from out of town during winter in Chicago, I don’t think you need to bring snow boots unless there is a lot of heavy snow in the forecast. (If there IS a lot of snow in the forecast, see below for snow boot reccos!)

I also would not advise bringing rain boots–it never rains THAT much, plus, rain boots don’t retain heat–your feet will freeze off. If you plan to walk a good amount, you will also likely want footwear options that cover your ankles from December-February (and potentially November and March if we’re being honest!), so that likely rules out flats and sneakers. (Unless you’ll be wearing them with tights, which could be a cute option!)

Snow boots I recommend: 

For those MOVING to Chicago, that’s a whole different ballgame. You will need a couple pairs of snow boots. I recommend having one pair of heavy duty snow boots (like tall Sorel bootssuper cute budget-friendly dupes here!) in your wardrobe for when there are several inches of snow on the ground, AND also a shorter, lighter pair (like these or these) for snow/slush that isn’t quite so intense. Reason being, big snow boots are hard to walk in, so you won’t need/want to wear them if there’s only an inch or two on the ground.

Other Chicago-winter-friendly boots: 

That all being said, boots and booties are going to be your best friends in Chicago winter weather–something that can get wet (regular leather is just fine as it’s naturally water resistant, as long as it’s not the delicate, buttery leather that will stain), and something with traction is ideal. Even if there isn’t snow in the forecast, there’s a good chance there will be leftover snow or ice on the ground, so traction is never a bad thing to have. Luckily, lug soles are super in right now–they’re a perfect example of a Chicago-friendly boot!

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 are visiting and have tall boots, you may want to consider bringing them! This is one reason I LOVE Blondo–they make great affordable footwear that is 100% waterproof. I’ve never been disappointed with a Blondo purchase, and I wear their shoes constantly during the winter. They’re ready to wear right out of the box!

Blondo’s Sierra boots are the tall pair I recommend to EVERYONE. 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! Blondo makes several types of boots, so whether you’re looking for something shorter or taller, with a heel or flat, etc, they have plenty to choose from. (Please note, these do not replace the snow boots referenced above. You will still not want to wear these trudging through half a mile in 8 inches of snow, for example.)

More options: 

These lace up booties are a good option to bring that are both practical and stylish! I also think Nordstrom brands have some great options that are water resistant and practical without breaking the bank–I have and love these lug sole boots from Caslon, and these Treasure and Bond booties are great too! I’ll link some of my favorite styles below!

Shop cute Chicago winter footwear options: 

Hats, scarves, and gloves really make a difference:

cute plaid scarf

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 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.

For example, a cute plaid scarf (Mango makes so many cute ones!) in 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 have a cashmere beanie I’ve owned for years that I wear everywhere and just found an exact dupe on Amazon for $39!) A winter beanie that is a cohesive part of your outfit, rather than an afterthought, will make your outfit look even more chic and add much-needed warmth.

I also recommend cashmere-lined leather gloves (I LOVE these and love that are also tech gloves!) or, if you really only care about warmth–puffer mittens will keep your hands warmer than gloves.

Shop cute cold-weather accessories: 

What to wear out at night in Chicago?

What to wear out at night in Chicago

25 Things to do in Chicago in the Winter (And What to Wear When It’s Freezing!)

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! We’re a pretty casual city.

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! (Well, at least nowhere I’ve ever frequented!)

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 (if I’m taking an Uber and don’t have to be outside very long, I like to opt for a cuter coat. ☺️).

I also 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!

I hope this was helpful in curating your Chicago winter wardrobe, whether you’re visiting, moving, or you’re a long-time resident looking to spice up your closet!

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