40 Winter Activities in Chicago: A Local’s Guide!

Seeking winter activities in Chicago? I admire your bravery.

A Chicago winter is no joke. We left the cold weather for sunny San Diego for a reason, and that reason was the last Snowmaggedon. 

There’s no hyperbole there. The blizzard in 2011 dumped more than 20 inches of snow on the Windy City and left drivers stranded on Lake Shore Drive.

Now that I’ve officially freaked you out, there’s also a sort of magic about Chicago in the winter. It’s not for the weak-willed, certainly. If you brave the likely travel delays and actually make it here, you’ll encounter a resilient city that continues to do what it does best: food, fun, and a cultural landscape like no other.

Let’s take a look at all of my favorite winter activities in Chicago, whether you’re staying inside or braving the chilly winter temps outdoors.

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Is it worth visiting Chicago in winter?

It’s absolutely worth visiting Chicago in winter. Prices are much lower on hotels and airfare, and most of the city’s best attractions don’t shut down. You just need to travel with a more flexible mindset.

Indoor Winter Activities in Chicago

What do people do in Chicago in the winter? In the winter, people in Chicago do many of the same things they do during the rest of the year. They visit the city’s best museums, indulge in the best food scene in the country, and fill their calendar with Chicago winter events.

The city doesn’t stop when temperatures dip. You don’t have to, either, especially when you’re in a city with so many offerings to bring you out of the cold.

Here are a few of my favorite activities when winter starts getting a little too real.

1. Embrace the ambiance of candlelight concerts.

We hit peak romance with a visit to the Stan Mansion, our wedding venue, for Fever’s Candlelight Concerts series. The ambiance was on point, and the Metropolis String Quartet that took us on our auditory adventure was engaging and funny.

Christmas music was on the set list for our visit, which only made things more whimsical. Yes, Queen Mariah made an appearance toward the end of a modern set.

They have quite a few themed nights all over the city at different venues that aren’t related to the holidays. We missed out on Taylor Swift night, but that’s typically my luck when it comes to Taylor Swift concerts.

When you go online to book, you’ll see different zones and varied price points. We didn’t see much of a difference between the zones at the Stan Mansion, but it’s not a huge space. There wasn’t a bad seat in the house. Do a little research on the venue in question if you’re worried about having a bad view for your show.

2. Make friends at a themed bar.

If you’re here around the holidays and want to embrace said holidays, prepare for a Christmas (or Hanukkah) explosion in Wrigleyville.

Yes, there’s a Hanukkah-themed bar called 8 Crazy Nights, and things do get crazy there after dark.

Start at Deuce’s Major League Bar for their annual Santa Baby popup. Reservations are highly recommended, especially the closer you get to the holidays. There’s a tented patio if you want to brave the weather with heaters, but it never gets too warm out there, so bundle up.

Come early for these regardless unless you like lines and drunk coeds. 

If Wrigleyville sounds like a nightmare, The Pink Squirrel in Logan Square is my favorite themed bar for year-round fun. It turns into Tinseltown over the holidays, but it’s a diner-themed bar otherwise. Both are great and all kinds of fun on a chilly evening.

Walk right in if you’re here for boozy milkshakes but make a reservation if you want to add a round of duckpin bowling to your night. If you’re rolling deep, they have some group punch bowl-like cocktails on the menu, including a set that comes in a little Ferris wheel.

3. Eat all of the things in cozy places.

Nothing warms up the belly more than an indulgent meal of something delicious. I like to make sure dairy’s involved in that plan, so my cozy places are going to feature a cheese-heavy time. First of all, Pequod’s Pizza should top any Chicago foodie list, but I’m not here to limit you in your winter adventures.

Bungalow by Middle Brow is another favorite. Come on a Friday for sourdough cheese (or caramel) boats, yummy pizza and beer, and the scent of Christmas trees all around if you’re there around the holidays.

If you’re already downtown doing all of the touristy things, pop by the Revival Food Hall. It’s particularly good with picky eaters since there’s a ton of variety. I like Smoque BBW for your meats, LaShuk Street Food for Israeli-inspired bites, and Bianca’s Burgers for (predictably) burgers but also po’boys.

My favorite in the food hall is Art of Dosa for South Indian dosas, curries, and vegan plates.

4. Feel like a kid again in Chicago arcade bars.

Arcade bars aren’t the rarity they once were, particularly in the best hipster cities around the country. Our favorites are Logan Arcade in Logan Square and the Emporium Arcade Bar. Emporium has three different locations in the city, but if you’re on an arcade crawl, their Logan Square location is just down the street from the Logan Arcade.

Those two are very much about classic pinball, arcade games, and rolls of quarters.

If you want something a little different, there’s another option that’s still on my list: AceBounce. This one is a ping-pong bar that looks like it’d be so much fun with friends.

5-9. Visit the city’s five best museums.

Chicago has the best museum scene in the country and winter is the perfect time to visit if you want to avoid crowds at the most popular options. Here are my top picks, whether you’re a first-timer or here for the classics:

• The Art Institute of Chicago: If you have your heart set on this one and only visiting during a particular time, book tickets online in advance, even during the off-season. This is one of the most popular museums in the country for good reason. You can spend hours inside wandering the halls and finding your favorite piece. 
• Chicago History Museum: If all you know about Chicago is that it’s pretty windy, this one is for you. Take a deep dive into the Great Chicago Fire, get to know Abe Lincoln on a more intimate level, and learn why a Chicago-style hot dog beats all other hot dogs at this fun museum.
• Field Museum: If you haven’t met SUE yet, you really should prioritize this one. She’s the largest and most complete Tyrannosaurus rex specimen ever discovered, and she’s glorious. I’ve been to this one too many times to count, but never miss the man-eating Tsavo lions, either.
• Museum of Contemporary Art: If you love contemporary art, you’ll want to visit one of the largest in the country. This one comes with a storied history, too. It hosted Frida Kahlo’s first exhibition in the United States. Andy Warhol, Kara Walker, and Jasper Johns are all represented here.
• Museum of Science and Industry: Brian and I are big enough nerds that we visited this one on our very first date during their special Harry Potter exhibit. If you visit around the holidays, expect festive displays that look at Christmas around the world. Don’t miss the U-505 Submarine, a German vessel captured by the U.S. Navy during World War II.

10-12. Visit three of Chicago’s most off-beat museums.

Chicago is known for its impressive museum scene, but that goes beyond the big five I mentioned above. Here are a few quirkier options if the snow and ice are really getting you down:

• Chicago Fed’s Money Museum: Take a deep dive into the Federal Reserve’s role in the economy and the history of money at this museum inside the Federal Reserve Bank of Chicago. There are quite a few interactive exhibits to keep you busy on a chilly day, including one where you try to tackle inflation. Fun!
• International Museum of Surgical Science: As I’m someone who loves places like the Museum of Death in New Orleans, this museum dedicated to the history of surgical science is a no-brainer for me. I always find advancements in medical tools and practices pretty fascinating.
• Intuit: The Center for Intuitive and Outsider Art: Chicago is a great town for art lovers, but that goes beyond the biggies like The Art of Chicago. This one celebrates self-taught artists and outsiders, so expect the unconventional on visits here.

13. See the fishies at the Shedd Aquarium.

The Shedd Aquarium was always my mom’s favorite spot when I was growing up. I’ve returned quite a few times as an adult since, and I totally get it. There’s something totally calming about watching all of those colorful fish swimming to and fro.

If you’re celebrating something special, there are some upgrades you can add to your regular admission ticket to make your visit pretty epic. Put on a pair of waders for an encounter with the Shedd’s resident beluga whales. If you don’t have a seafood allergy, you can add on a stingray feeding session at the aquarium’s touch tank.

You’ll get instructions on keeping the animals safe and happy if you choose a special enhancement. There are some restrictions on each one that you’ll need to read through before booking.

14. Treat yourself to a spa day.

Taking off that sleeping bag coat gets quite a bit easier when there’s a spa treatment awaiting you on the other side. Visit the Oxygen Spa Studio in Humboldt Park for seaweed wraps, customized facials, and stress-busting massages. The Ruby Room in Wicker Park offers readings and healings on top of its broad roster of massage services.

If you’re all about a luxe bathhouse, AIRE Ancient Baths in River West offers unique packages that include thermal baths, candlelit massages, and soaks in red wine. The idea is that your body benefits from the antioxidants in red wine through the skin and not only down the gullet.

This place is pricey, but if you’re here in the city for spa times you’re likely ready to drop some coin.

15. Warm up in the dome at Garfield Park Conservatory.

Thaw out a bit with a visit to the steamy Garfield Park Conservatory, one of the largest conservatories in the country. Hang up your winter coat upon arrival and walk jungle paths through exhibits of ferns, desert cacti, and a winter wonderland decorated with poinsettias.

It’s basically like putting on a cozy blanket in this place.

The dome has been operating in some form since 1908. Don’t miss out on the koi pond where you can wonder about whether the teeny tiny ones are ever at risk of becoming a snack for the monster koi. It haunts me.

Book a free ticket time online before you go. While we had no issues with limited tickets on our visit, it can get busy around the holidays. Park in the attached lot if you drive.

16. Visit Lincoln Park Conservatory, too.

The conservatory in Garfield Park is more impressive, but Lincoln Park is easier to get to. If you’re really into botany and already in Lincoln Park, a trip to the Lincoln Park Conservatory is a great way to warm up in the winter months. 

This one is an easy add-on to trips to the Lincoln Park Zoo. The two are next door to one another. Oh, and they’re both free!

17. Jump around at a trampoline park.

I swear the kid in that photo above was having a really good time.

Assuming you don’t suffer from vertigo — is jumping around in rapid fashion supposed to make you feel nauseous? — an indoor trampoline park is a great way for adults and little ones alike to burn off some energy.

We love Altitude Trampoline Park in Skokie, a suburb just outside the city limits, but there’s an Altitude Chicago just north of the West Loop if you don’t have a ride. All jumping sessions come with your own pair of grippy socks for a safer experience.

18. Take in one of Chicago’s indoor festivals.

Chicago has one of the best festival scenes in the country. While summer certainly sees outdoor events come alive, the fun doesn’t stop just because temps fall below freezing. Some festivals just take the party inside.

Here are a few to watch for if you’re visiting Chicago in the winter months:

• Chicago Wine Fest (December): Enjoy a variety of wines from near and far with food and live music, too. Early admission tickets get an extra hour of wine time.
• Chicago Ale Fest (January): Is wine not your thing somehow? This festival boasts over 100 different ales, food trucks, a DJ, and a variety of games and activities that likely get more fun as the day wears on.
• Chicago Theatre Week (February): If you love live theatre but don’t love the often high price of show tickets in entertainment hubs like Chicago, get value-priced tickets during this annual event each winter.
• Chicago Auto Show (February): If you’re already into cars, you likely know that this is the biggest car show in the country. As such, book your Chicago travel well ahead of travel for this one.

19. Cheer on the local teams.

Soldier Field is an outdoor venue, but if you’re not into watching concussions on the field while freezing your own brain, you have options. The United Center is a raucous time during Bulls and Blackhawks games, and both play throughout the winter months.

This is where I admit that Brian used to get box seats to games in the city while he was working in the insurance industry. It’s a perk I miss, as my sports outings involved free chicken fingers and cocktails. I promise Chicago games are still super fun if you just buy the regular tickets.

20. Hit a farmers market.

Yes, this is still the indoor activities list. The Wicker Park Farmers Market hosts an indoor winter market from December through April at The Robey on North Avenue.

It only happens on select Sundays, so check the website for their schedule if you’re interested. Bring your own shopping bags if you’re here for more than window shopping, too. The city’s big on reducing waste.

21. Yuk it up at Chicago’s best comedy clubs.

Chicago’s comedy scene doesn’t hibernate. Yes, that’s a real photo of me with Eugene Levy at an anniversary engagement at The Second City. I got to meet Danny Pudi and Fred Willard at the same event, so if that does anything for you, I love that.

The point here is that Chicago has a stellar comedy scene. The Second City is the biggest name, but you have options if this is what you came here for. Here are a few more of my faves:

• The Comedy Bar: Tucking into some stand-up comedy while indulging in a full menu from Gino’s East feels very Chicago. No, it’s not my favorite deep-dish pizza, but evenings here are always full of laughs. Come back in the warmer months for outside seating and a different kind of experience.
• The Revival: No, this isn’t a comedy show at a food hall. This stand-up and improv club is in Hyde Park on Chicago’s South Side, and it boasts an impressive comedy history. The common wisdom is that improv was born on this site thanks to the Compass Players, a troupe that improvised short plays, back in 1955.
• Zanies: Up-and-coming comedians and veteran comics alike love coming to Zanies, one of the city’s top stand-up venues. The club in Old Town has changed very little since its opening more than 30 years ago. That may be good or bad depending on what you’re after. Expect a two-drink minimum either way.

22. Take in some theater.

If live theater is more your speed, the scene in Chicago is an impressive one.

Visit the Lookingglass Theatre Company if you’re a big fan of that one scene in Friends where Ross keeps yelling “PIVOT!” as he tries to direct Rachel and Chandler around the proper way to maneuver a couch. (David Schwimmer is a co-founder of the theater.)

The Goodman Theatre is the first stop for all kinds of big names on their way to Broadway. Brian lived right next to this one for a bit, and his building was also where those big names stayed during their runs at the Goodman. We both had a run-in with Philip Seymour Hoffman in the lobby while he was doing The Long Red Road.

For the biggest musicals and Broadway right here in Chicago, check out:

• the Cadillac Palace Theatre,
• the James M. Nederlander Theatre (previously known as the Oriental Theatre), or
• the CIBC Theatre.

23. Go to a live show.

As with its comedy scene and its live theater, Chicago has plenty of indoor venues suitable for live musical acts big and small. If you love a good hole-in-the-hall, head to the Empty Bottle in Ukrainian Village. Those who love true crime won’t want to miss the Green Mill, a cash-only lounge that was once a favorite of Al Capone.

Want something with a bit more caché but that still feels quite intimate? The Metro rewards those who brave Wrigleyville with a venue that has hosted the Smashing Pumpkins, Fall Out Boy, and Chance the Rapper.

I’m mostly kidding about being brave in Wrigleyville. The neighborhood just makes me feel so old.

Outdoor Winter Activities in Chicago

Fun Chicago winter activities are also about embracing the cold. If you’re some kind of cold weather freak, I applaud you. If you aren’t, you can still have fun outdoors in Chicago, especially if the roads are clear. Just bundle up with layers and take care of those extremities. Frostbite is no joke!

24. Celebrate the holidays with three different Christkindlmarkets.

Chicago’s holiday markets are often recognized as some of the best in the country. Some would say they even compete with the European markets. I’m not sure I buy that, but there’s only one way for you to find out.

Start with the original downtown location for the best of the three Christkindlmarkets. The Gluhwein is a must but spend as much as seems feasible for your budget. These markets can get pricey if you’re not careful, as there does seem to be an upcharge on holiday fun. 

If you’ve been there and done that, visit the Wrigleyville market next. I encountered one of the worst lines of my life at the mini donut stand at this, but it was also a Saturday. My point is, don’t go on a Saturday. 

Suburban friends, you’re not out of luck here. There is a third Christkindlmarket in Aurora. I can’t vouch for that one, though, as I’m not going to Aurora when there are two markets in the city for me to overspend at. It is what it is.

25. Pop by Winterland at Gallagher Way while you’re at it.

For an upgraded experience at the Wrigleyville market, pay $5/person to get into Winterland at Gallagher Way. You can purchase tickets to ride holiday rides or go ice skating on the field, which is all as whimsical as it sounds. It can get expensive.

My favorite Winterland stop is the drinking tent, if only because you can warm up in there. Get a refill in your Gluhwein mug and sidle up to some strangers as you sip. Spiked hot chocolates and hot ciders are also an option, but you don’t get the deal on refills with those.

26. Visit the City of Chicago Christmas Tree.

It’s hard not to feel something once you see a 55-foot (or more!) beauty all lit up and ready for the holiday season. Visit anytime after the tree lighting, a celebration that happens before Thanksgiving, through the first week of January. You can find the City of Chicago Christmas Tree in Millennium Park near Michigan Avenue and Washington Street.

27. Have a meal outside…sort of.

Having dinner and drinks in an outdoor igloo has been trendy for a few years now, so you may as well see what all of the fuss is about. These do require some planning, and expect to see an upcharge around the holidays. I find that traveling in a small group is best for these things so that you can split the costs.

Here are some outdoor igloo options for Chicago winter visits:

• I|O Godfrey: This lounge at the Godfrey Hotel features a retractable roof that keeps the party going no matter how low the temperatures go. The real draw at this River North spot is their Winter Wonderland, complete with clear domes and seasonal cocktails that will make you feel like the star of your own holiday Netflix movie.
• Joy District: It’s impossible to talk about iconic winter spaces in Chicago without mentioning Joy District in River North. If you visit around the holidays, this rooftop becomes the most festive ski chalet you’ve ever seen. They have s’mores boards for Pete’s sake.
• Kennedy Rooftop: Sip on bubbles while sharing (or not) the signature brownies at the rooftop bar of the Hyatt Place Chicago/Wicker Park. Book an igloo ahead of your visit on their website. They also have curling lanes. If you love the sound of that, I have more options for you if you keep on reading.

28. Shoot the duck on the Ice Skating Ribbon at Maggie Daley Park.

I’m not talking about harming waterfowl. “Shoot the duck” is a cool move to try out on the ice skating Chicago rink to impress your friends. It’s best to time it after a clumsy display to really start some shock and awe out there.

In any case, the Maggie Daley Skating Ribbon is the most scenic ice skating rink in the city for all of your best moves. Here are a few tips to make it even breezier:

• DO make a reservation, especially when it’s beginning to look a lot like Christmas. You’re not the only one interested in doing cute winter things, and popular dates/times do sell out. You can rent skates at the ice skating rinks, too.
• DO take the train down if you’re able. Parking downtown is expensive. If you’re visiting, make use of the network of trains and buses in the city. You don’t get this kind of public transit everywhere in this country!
• DO visit on a weekday. We would have had no issues walking right up for a time on an overcast Monday morning and had quite a bit of room on the ice to get our warmups in.
• DO arrive at the start of your booked time. This is even if you don’t think you’ll be out there for the full two hours. It’ll take you a while to get those laces just right, and you don’t want to be rushed off by the Zamboni in between sessions.
• DO rent a locker for your stuff. You don’t want someone to lift your sneaks while you’re out there with your penguin assistant. I refuse to think about navigating the Blue Line without any shoes on. 

Note: If you’re a beginner, there are little penguins and other fun characters available for rent in the locker room to help you learn what to do with your feet. They’re great for skaters with special needs, too.

29. Check out more of Chicago’s best ice skating rinks.

Here are two more rinks to check out if you’ve already been to the ribbon:

• McCormick Tribune Ice Rink: Skate with views of Michigan Avenue and Cloud Gate, or “The Bean” at this ice rink in Millennium Park. Admission is free but you need to reserve skating times online before you go. Skate rentals are available on-site.
• Navy Pier: The People’s Pier really turns it on in the winter months with Light Up the Lake, an indoor lights experience that runs through the start of January. The experience includes an indoor skating rink for snowy days.

30. Embrace winter at Polar Adventure Days at Northerly Island.

Polar Adventure Days is a free event held on two separate days each Chicago winter. All of the activities are outdoors — this is a celebration of the cold, after all — so arrive at Northerly Island bundled up and prepared. Activities include dog sled racing, snowshoeing, winter crafts, and tours of the Northerly Island Natural Area.

Limited paid parking is available on-site, but don’t be surprised if you have to find a paid lot elsewhere. Public transit is usually great in the city, but you’ll need a bus and a train combo to get to Northerly Island.

31. Bundle up for the Chicago Botanic Garden.

It pains me to say that I’ve yet to see Lightscape at the Chicago Botanic Garden. This one sells out fast, so you need to be quick on the draw with plans. The one year I did get a set of tickets, a bomb cyclone came through to cancel the event.

This is what I’m saying about being flexible with your plans. If you arrive and there’s a blizzard happening, take the party indoors. That’s if you get to Chicago, of course. That same bomb cyclone canceled a bunch of flights coming into O’Hare International Airport.

That all said, it looks fantastic and whimsical and bills itself as a journey through music, light, fire, and color. What’s not to love about that?

After the holidays, the gardens retain their regular hours for those willing to brave freezing temps for a botanical stroll. They don’t close down for minor snowfalls, either, which sounds quite scenic.

32. Love a garden light show? The ‘burbs have another!

Illumination at The Morton Arboretum is another light spectacle with displays showing off the park’s 50 acres. If you’re not bringing your mother, they’ve added a late-night Electric Illumination option that sounds like a dance party. You have to be 18 or older to attend. As I’m not even sure what “trance” music is, I think I’ve already aged out of this one.

33. Get up close and personal with The Bean.

If you’re already strolling the Magnificent Mile, your day wouldn’t be complete without a visit to The Bean. 

Fun fact: The sculpture’s official name is Cloud Gate. If you’d like to impress some locals while you’re there snapping your photos, by all use its given name loudly and proudly. They may just think you’re obnoxious. More likely, they’re at home because this is a touristy activity to the max.

The sculpture is at its most scenic after fresh snow. You get a dusting on The Bean itself, making those reflective selfies even more adorable.

34. Work on your (cross-country) skiing skills.

When there’s enough snow accumulation, the Morton Arboretum in nearby Lisle has trails for cross-country skiing (and snowshoeing!) for those who want to work up an appetite for all of the cozy treats. They have equipment rentals there for you, too, if you don’t have your own.

You’ll need to wait for at least four inches of snow on the ground and their annual light shows to conclude around mid-January. Ski routes are available online if you’re a planner.

If you’re already in the ‘burbs and want more variety in your trails, you’ll find a more full-service option in Lemont at the Sagawau Environmental Learning Center. Each winter, the center becomes Sagawau Nordic, with ski rentals, lessons, and groomed trails for winter sports enthusiasts at all levels.

35. Visit the Lincoln Park Zoo

The free Lincoln Park Zoo is open 365 days a year. You read that right. You can see all kinds of critters for free every single day of the year. 

Fun fact: Visiting in the winter allows you to see what the animals do when temperatures dip below freezing. Do they layer on the sleeping bag coats as I do, or play in the snow? The animal houses for the more fair-weather creatures remain open during regular hours.

If you visit around the winter holidays, expect the zoo to close early to prepare for ZooLights. This is a good thing if you like zoos after dark and that Christmas spirit. Tickets for ZooLights are free on Mondays and just $5 otherwise. They can be reserved in advance.

If you want to ditch the kids, look for their adults-only Holidaze night, complete with hot libations like spiced wine. You likely won’t see a ton of animal activity at this nighttime event, but it may give you your first glimpse of the elusive nocturnal aardvark.

Book tickets for this event ahead of time as they do sell out for good reason. It’s a very fun, whimsical time…except for when the DJ starts playing “Get Low” at the zoo’s bar and grill. That’s not as whimsical.

36. Go sledding.

If you’re looking for family things to do in Chicago this winter, find a plastic sled — are garbage can lids just in the movies, by the way? — and shove those kids down the nearest sledding hill. 

Note: This one is definitely weather-dependent. If you’re visiting on a 50-degree day in December, you should count your lucky stars and enjoy a meal on a patio, instead. Your plan for winter in Chicago should be to prepare for everything, including a Chicago winter storm.

Here are a few options for the best sledding hills Chicago has to offer: 

• Caldwell Woods: This small preserve on the northwest side makes up for its size with its proximity to Superdawg. If you’ve never visited the blinky-eyed cartoon hot dogs that terrorized my youth, you’re missing out on the best dogs in the city. The sledding hill itself is lit up and staffed during regular business hours.
• Dan Ryan Woods: If there are at least three inches of snow on the ground, hit this nature preserve on the city’s South Side for some sledding action. If you’re on the website, you want the location known as the Dan Ryan Woods Visitor Center at Western Ave and 87th Street. The hill is lit up and staffed during regular business hours.
• Humboldt Park: The small hills in the park don’t operate in any sort of official capacity, so be mindful of that if you go and practice safe sledding. That said, we saw quite a few kids of all ages tearing it up out there during our month-long stay in the neighborhood.

37. Marvel at a frozen Lake Michigan.

When things get blustery and the city’s first round of blizzards hits, the brave souls who wander out in the aftermath are treated to some pretty epic scenery. Go check out what the weather has done with the ice on Lake Michigan, the second-largest of the Great Lakes if we’re talking volume.

You may even get to see some pancake ice. That’s when the ice forms into little circles that resemble pancakes if they were…circles of ice. Loyola Beach in Rogers Park is a great place to start if you’re not sure where to focus your efforts.

38. Celebrate the Lunar New Year.

I already shared the indoor fun you can have at some of the city’s best winter festivals. When it comes to the Lunar New Year, Chicagoans who celebrate take the party outside. Chinatown is where it’s at if you’re looking for traditional lion dances and the annual parade for Chinese New Year.

The Argyle Lunar New Year Celebration in Uptown is another large event that features a parade, cultural dances and performances, and a celebratory atmosphere. Public transportation is encouraged for both, as these events are well-attended.

39. Realize that curling is actually pretty dang hard.

Fun things to do in Chicago in winter should always include potentially making a fool of yourself.

I went curling on a date once in my 20s. Everyone left quite sheepish after spending days leading up to the date talking smack about how this could possibly be an Olympic sport. There was sweeping and everything.

If you’re in Chicago, there are a few options for you to try your own hand (or arm?) at what I’ll call shuffleboard on ice. Most of the experiences you’ll have in Chicago will be modified for what I can only assume are liability purposes, but you’ll get the idea.

Here they are:

• Gwen Hotel: Reservations for Curling & Cocktails at the downtown Gwen are available in 45-minute intervals for up to 10 friends at a time. The rink on the terrace isn’t made of ice, but you do get a cocktail with your booking. The cost is $40/person.
• Kaiser Tiger: Reserve a rink at the West Loop’s Kaiser Tiger for 40 minutes per session. The cost is $70/curling court, so this could get economical if you roll deep. If you want a heated table in the beer garden, too, those reservations are separate.
• Lakeshore Sport & Fitness: Curl to your heart’s content — or in this case, for 30 minutes each session — on the synthetic ice at this Lincoln Park rooftop. Lane reservations are just $30, and you can bring up to eight friends up there each time.
• Whisky Business: This Wicker Park bar has a year-round expansive rooftop, and is likely easier to get to than the other locations downtown. Not into curling? Check out their heated igloos.

If you want to turn pro one day, you can also learn how to curl from one of the local curling clubs. The Chicago Curling Club offers Learn2Curl classes for newbies with no prior experience required.

40. Take a day trip to frozen waterfalls.

Illinois isn’t Oregon, but if you know where to look and have a car with good traction to get there, you can find some pretty spectacular examples of frozen waterfalls, or icefalls, outside the city.

Starved Rock State Park in Oglesby, an hour-and-a-half outside the city in light traffic, offers the most bang for your buck.

You can hit just about any of the big trails there and see something magical in the winter. If you like a little more guidance, start with the French Canyon Trail. The full trail is 2.5 miles long, but you’ll get to your first icefall in just half a mile from the visitor’s center. If you’re not here to play, the hike to LaSalle Canyon and its cascading falls is just over 4 miles in total.

Use the park’s trail maps to better plan your day. If you’re bringing your pup, make sure this isn’t the first time they’re hiking in the winter months. Not every dog can handle the cold, the ice, and the snow!

What to Pack for Chicago Winter Attractions

I like my travel tips all kinds of thorough, and that includes what to pack for a more pleasant Chicago winter stay. The key to navigating Chicago winter months is layers.

If you love to avoid checking your bag, bring your biggest coat along with you on the plane. You’ll save quite a bit of room that way. Let’s get on with your Chicago winter packing list, shall we?

Fleece-Lined Leggings

Oh, how nice it is to have something warm right up against those legs. This is especially true if you don’t bring a very long coat. One pair of fleece-lined leggings is enough to keep you toasty as a base layer or, if it’s not too chilly, as a solo layer underneath a long sweater.

Fleece Tights

If you want that fleece goodness all the way down to your feet, bring along a pair of fleece tights, instead. I like layering these underneath a pair of jeans to keep things nice and toasty underneath. They’re thin enough to keep you warm but not so bulky that they’ll bunch under your pants. Jeans are the worst in the winter months, by the way.

Layered Shell

If the temperatures aren’t dipping too low during your visit and you know you want to stay active on a Chicago winter trip, a layered shell may be a good alternative to the bulky sleeping bag coat I’ll recommend down below. Most layered jackets come with a warm layer on top of a water-resistant one to keep you dry and cozy.

Long Underwear

I’m more likely to find myself wearing fleece leggings and fleece tights, but thermal undies aren’t a bad call if you know you’ll be spending quite a bit of time outside. Brian likes his for outdoor sporting events and when we’re out in the winter wild trying to get some steps in.

Sweaters

You’re obviously not packing crop tops for your Chicago winter vacation. I love a good oversized sweater, but comfy cardigans are another option if you like to layer. I know sweaters take up more space than most other clothing items, but a good base layer will allow you to wear them a few times during your trip.

Thermal Tops

Thermal tops are meant for layering. They’re close to the body so they don’t add much bulk, making them a great addition to your oversized sweaters. If you’re hitting the ice rink or doing other aggressive outdoor activities, they wick away moisture, too. Getting all sweaty in sub-zero temperatures is painful.

Warm Hat

While you do lose heat through your noggin, that claim is a little exaggerated. (It’s nowhere near half of your body heat or whatever your mother told you back in the day.) That said, a cold head is the WORST. Top yourself off with something cute and you’ll be much happier participating in these Chicago winter activities.

Winter Boots

More often than that, a Chicago winter visit means you’re dealing with snow and ice. Locals try their best to keep up with the accumulation by salting the sidewalks, but bring along a pair of winter boots with some traction anyway. You don’t want to embarrass yourself in a pair of heels you thought would look cute in those Chicago bars.

Winter Coat

I like what I call “sleeping bag coats” during Chicago winters. They go well below the waist and basically resemble a sleeping bag with arms. Anyone with me tends to stop making fun when I’m the only one feeling all warm and cozy while the rest are fighting the shivers. Bring along a longer coat that covers your bum to feel a similar amount of righteousness.

Winter Gloves/Mittens

If your hands are cold, everything else will feel that much worse. I like to wear a touchscreen pair when I’m out and about so that I get all of that hot content. Here’s another pair if you move through the world in a similar fashion. A cute pair of mittens is always a good idea, too.

Wool Socks

Wool socks are perfect no matter the weather because they keep your feet both dry and warm. If you’re visiting Chicago in the winter, you’ll want longer wool socks that offer your legs more coverage. They’re thicker than usual, so they’re a great base layer if you’re doing any winter sports, too.

Where to Stay on a Chicago Winter Trip

You’ll drop some bucks no matter when stay at Chicago’s best downtown hotels, but the bucks won’t be as aggressive in the winter months. 

If you’re visiting over the holidays, it doesn’t get much better than the Chicago Athletic Association Hotel. They host an annual Christmas pop-up bar called Happy’s Bar. Expect winter libations and all of your favorite holiday pop songs.

Here are a few more options for Chicago winter accommodations from my preferred hotel site Booking.com:

• Acme Hotel Company Chicago: This River North boutique hotel has all kinds of entertainment on-site in the case of inclement weather. Enjoy small bites and craft cocktails in the bar for starters.
• The Buckingham Hotel: This one is actually inside the Chicago Stock Exchange building. Stay in the thick of it at this luxe downtown option.
• The Emily Hotel: If you’re here to eat your way through Chicago, it doesn’t get much better than a West Loop hotel. Guests love the decor and coffee shop in the lobby.

Traveling in a group? These picks from Vrbo may be more cost-efficient:

• Try to feel young at this two-bedroom close to Wrigley Field. All I mean by that is that Wrigleyville makes me feel very old. This apartment looks very cute, though.
• Stay in between Bucktown and Logan Square, one of my favorite Chicago neighborhoods, at this two-bedroom. Guests love the location and access to public transportation.
• Whether you’re here for sports or dining, this option in the West Loop is well-situated for both. Reviews love the location with easy access to the best of Chicago in winter.

Chicago Winter FAQs

How do you enjoy Chicago in winter?

You can enjoy Chicago in winter by embracing the chill or enjoying the best of the city’s indoor activities.

Locals may not love the idea of Chicago in winter but that’s because they have to navigate traffic, public transit, and getting to and from their daily activities in the winter months. You’re here to play. If the cold doesn’t bother you anyway, the winter is a fine time for a trip to explore fun things to do in Chicago in the winter.

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