chicago winter survival guide

This content uses referral links and contains affiliate links to products. We may receive a small commission for purchases made through these links at no cost to you.

So you find yourself living in Chicago in the winter? I’m so sorry, but here’s the good news. You have automatically earned the right to hibernate. That’s right. How do you think we make it through a busy, action-packed summer? Ha! Because we have conserved our energy by hibernating all winter.

Here is your Chicago winter survival guide with tips from a Chicago native if you are new to this long, sometimes unbearable & brutal season. And if you are a local, some things to get you out of the house.

Layers are key. Personally, I recommend a thin underlayer & cashmere. I know, I know cashmere is expensive, but you don’t have to go crazy. Just a few good pieces will suffice since, believe it, or not some winters are too warm for cashmere. This link brings you to Quince, where I get my favorite, reasonably priced cashmere. Think of it as an investment that you will have for a very, long time. Cardigans are the perfect style to choose because they are versatile and you can wear them all year. I also love the cashmere tee, hoodie & wrap. I really do use them all year round. Also, good ol’ wool sweaters are a lifesaver. Wool adjusts to your body temperature, keeps you warm even when it gets wet, and is odor resistant.

I found some bargain, recycled cashmere at the Randolph St Market. They have a variety of sweaters for $20 (!) and repurposed cashmere items as well. I got a grey cardigan & some fingerless gloves that I just love and have worn a ton already. Read my post about the Randolph St Market here.

While we can’t predict this winter it’s not looking good since we already had snow on Halloween and in the past couple of weeks we’ve broken a 150-year-old record of the coldest first half of November.

I also recommend a couple of good humidifiers. My vintage apartment is sweltering from dry radiator heat, and I often have to crack my windows. I have a couple of Venta humidifiers that work really well. Again, these are pricey but worth the investment. They are easy to maintain (no filters), clean, and make a huge difference.

We are in for many grey days ahead. If you are prone to SAD (Seasonal Affective Disorder), get a light therapy lamp. Here’s the one I bought, and bonus, it doubles as a light needed for Zoom meetings.

Get a flu shot, please. The flu can be life-threatening. I know you are too busy to make an appointment to see your doctor to get one, but that’s not necessary since they offer them everywhere, Walgreens, CVS, and usually your local grocery store pharmacy, and it’s usually covered by insurance. Here are locations for free flu shots in the city. I got mine at City Hall. Please get one and stay healthy.

Seriously, winter in Chicago is never consistent except for lasting too long. Sometimes it’s mild & doesn’t get really bad until January or we get a ton of snow or like last year bitter cold. Best to be prepared.

Must-have basics include a parka with a hood (a hood is key), waterproof boots, wool socks & of course all of the accessories, hats, scarves & gloves.

Finally, a streaming service (Netflix, Prime, Hulu or all three) and some kind of grocery shopping delivery service. I just signed up for Instacart and just got my first delivery. Genius.

But what about when you get a bad case of cabin fever? Here are some suggestions to get you out of the house.

find a cozy bar with a fireplace

If you are fortunate enough to have a fireplace in your home that’s great but if you don’t here are some bars that do. Some of my favorites are the Grafton, a great Irish pub in Lincoln Square, swanky Library Bar in the Ambassador Hotel in the Gold Coast and Simon’s a great dive in Andersonville. Stop in at Simon’s for some glogg before or after dining at the Hopleaf down the street. Get the mussels or fried chicken (Monday nights) and enjoy their extensive beer selection or get my favorite beer, Duvel.

go ice skating, sledding or snowshoeing

If conditions are just right, like fresh snow on the ground and bearable temperatures, grab your snowshoes and head to the lakefront or a nearby park. What?! You don’t have any snowshoes? Well, go get some. Really, you’ll thank me later. I use mine a lot when there is enough snow. The lakefront is quite breathtaking & peaceful after a snowfall and it’s a great workout. It’s my winter meditation.

Or bring the kiddos to Cricket Hill near Montrose Beach and go sledding.

Pretend you are a tourist and go to Millennium Park and skate under the Bean or head over to Maggie Daley Park and check out the Skating Ribbon. Bring your own skates to skip the line and the $13/15 rental fee.

I got a pair at Play It Again Sports because growing up in the midwest, we had an ice rink in our backyard and learned to ice skate very young. The Skating Ribbon at Maggie Daley Park & Millennium Park skating rink opened this past Friday and runs through March 8.

Here are links with details about ice skating throughout the city & the best sledding hills in the city & suburbs.

go to a museum

We have a lot of great museums here in Chicago. Some well known, some obscure and they cover a wide variety of topics. If you want to tackle the Art Institute, which I highly recommend, I suggest you get the app. It makes the second-largest art museum in the U.S. (1 million sq ft!) much more manageable. You can see specific world-famous masterpieces based on the time that you have or genre you are interested in. I’ve heard wonderful things about the current Warhol exhibit that runs through January 26, 2020.

Some of my other favorite museums include the Cultural Center, the Museum of Contemporary Photography at Columbia College, the Chicago Design Museum and the National Museum of Mexican Art (all free). Here are my posts about the Chicago History Museum & wndr museum.

Go to MSI (Museum of Science of Industry) for their annual Christmas Around the World and Holidays of Light exhibit. It began on Thursday, November 14 and runs through Sunday, January 5, 2020. More must-see exhibits include Colleen Moore’s Fairy Castle, Science Storms, Wired to Wear & the U-505 Submarine. This ginormous place is even larger than the Art Institute so you will want to allow enough time to see everything on your list. Did you know that this building was the former Palace of Fine Arts from the 1893 World’s Columbian Exposition? The only remaining building from the World’s Fair/White City.

Some museums may offer discounts through Groupon. Click here.

go to a conservatory

Around since the late 1800s, the Lincoln Park Conservatory has been a longtime respite for Chicagoans. It’s a lovely place to visit all-year-round but especially in the winter months when the tropical warmth & lushness is much needed.

Garfield Conservatory, one of the largest conservatories, showcases thousands of plant species from around the world throughout eight indoor display gardens.

be a tourist in your own city

They have been setting up the Christkindlmarket for the last couple of weeks and it opened this past Friday. Since 1996, it’s like walking into a quaint German village but in Daley Plaza, in the heart of the Loop, with the Picasso peeking out above it all. Many of the vendors come from Germany and display their beautiful wares ranging from delicate glass ornaments, handmade hats & scarves to intricate wood carvings. It gets pretty crowded so I prefer to go late afternoon to satisfy my craving for potato pancakes and Glühwein a traditional hot spiced wine. I wonder what the souvenir mug will look like this year? November 15 – December 24

Go to the historic Marshall Field’s building/Macy’s to check out the holiday windows on State Street, then go inside to warm up and check out the Great Tree in the beautiful Walnut Room (7th floor). While you can dine under the tree, it gets pretty crowded, and they don’t take reservations during the holidays, so I suggest trying the wine bar.

Go check out the heated domes available on the River Walk and various other spots throughout the city.

be thankful & give back

Volunteer at your neighborhood food pantry or utilize your unique skills elsewhere. Click here to find a good fit.

Hopefully, you’ll be so busy with all these things to do you won’t even notice the cold. Haha, yeah right. Follow my Chicago winter survival guide and you will survive. Good luck & see you in Spring.