43 Cozy Things to do in Chicago in the Winter (a Local’s Guide)

Go Ice Skating

One of the best things to do in Chicago in the winter is to go ice skating! Gliding on the ice underneath Chicago’s glittering skyscrapers and holiday lights is one of the most magical things to do in Chicago in the winter.

There are plenty of options for ice skating in Chicago! Here are a few of the best outdoor ice rinks in the city:

• Millennium Park Ice Rink: Skate at the famous Millennium Park on the McCormick Tribune ice rink! You’ll glide underneath the soaring Chicago skyline and right past the Bean. The rink is open for ice skating November through March (exact dates vary each year) and admission is free (though you’ll need to rent skates). This is one of the most popular things to do in Chicago in the winter, so be ready for long lines to enter – but trust us, it’s worth the wait to glide under the sparkling lights and festive atmosphere.
• Wrigley Square Ice Rink: During the holidays, Wrigley Square turns into “Winterland at Gallagher Way.” Some of the best Chicago Christmas (and Hannukah) events even take place at this popular Chicago winter attraction, like a Christkindlmarket, Santa’s Workshop, wreath-making classes, holiday movies, ice bumper cars – and of course, ice skating!
• Grant Park Skating Ribbon: Ice skating on a rink? Anyone can do that! How about ice skating on a path through snow-dusted pine trees through a winter wonderland? Called a “skating ribbon,”  the Maggie Daley skating ribbon path in Grant Park is twice the length of a lap around a regular ice skating rink – a fantastic challenge for intermediate skaters. The skating ribbon opens in mid-November.
• Hyde Park Ice Skating Rink: The Midway Plaisance ice skating rink is located in one of Chicago’s most iconic parks, at the very site where the 1893 World’s Fair was hosted! Come here to skate or play hockey with friends and family.
• The Sky Rink: Ice skating on top of a hotel? Yep, it’s a thing: the Sky Rink at the Peninsula Chicago sits high above Michigan Ave, high above the busy street and surrounded by Chicago’s skyscrapers and twinkling lights – the perfect place to admire the view while sipping on some hot cocoa. Make a day of it and enjoy a festive Holiday Afternoon Tea before you skate! Note that this is one of the few ice skating rinks that isn’t free, but the price of admission ($20 for adults, $10 for children) includes skates and benefits children’s charities.

Believe it or not, there are even more ice skating rinks in Chicago! Get the full list here.

Explore Chicago’s History 

Chicago bore witness to many of America’s most fascinating stories throughout history: prohibition, the Great Chicago Fire, the World’s Faire, a bunch of serial killers, Al Capone… well, put it this way: pretty much anything seedy or underground that you can imagine, Chicago was ground zero. (Speaking of, definitely read the Devil in the White City before your trip!)

That said, although most tours of Chicago are around The Loop and focus on these topics, there is so much more to the city’s multi-layered history than Al Capone!

Here are some ways to dive into Chicago’s history:

• Take a “Gangsters and Ghosts” walking tour through the Chicago Loop, known as the vice district during the 1920s and 30s. You’ll see the places where gangsters such as Al Capone used to party, make deals, and carry out business, and hear the chilling stories of the ghosts who still haunt Chicago’s streets.
• Walk around the Pullman neighborhood, which was once the site of the country’s first planned industrial community. Most people (locals included) overlook that the founder of the Pullman sleeping car, George M. Pullman, created a planned community in the late 1800s where his workers lived, worked, and played. Designated a national monument in 2015, visitors can walk through the carefully crafted historic sites that once were the daily life of thousands of laborers. You’ll see plenty of Queen Anne-style brick buildings that were old worker’s homes, manufacturing sites, a church, a museum, and more. 
• Take a Chicago Mahogany Tour led by Sherman Dilla, Chicago historian, first gaining notoriety on Tik Tok. Dilla, as he’s called, takes visitors on bus tours through overlooked Southside neighborhoods like Chatham and Roseland and discusses important African American figures often erased from history, like Daniel Hale Williams, the first person to successfully perform open-heart surgery. 
• Despite what the name might suggest, Chicago for Chicagoans is a great way for visitors to explore the city. The pay-what-you-can tours, lectures, and scavenger hunts focusing on Chicago neighborhood history give visitors an insider look at the impact of immigrants, forgotten history and the industries that built the city. Plus, the events are run by locals, so you can ask them for recommendations and hear their stories. All of their tours are fascinating, but we highly recommend making sure to grab your ticket for an Andersonville tour if you love Swedish history or McKinley Park to learn about the city’s manufacturing roots.

Eat Famous Chicago Food 

Listen: if you visit Chicago and don’t eat a slice of cheesy, buttery deep-dish pizza, did you really visit Chicago??

There are some foods locals love to hate, and many Chicagoans roll their eyes at our reputation of consuming deep-dish pizza. And sure, much of the city’s most famous food (you know, the greasy, heavy, dense stuff), is often dubbed touristy or inauthentic… but you’ll still find locals lined up around the block because it’s yummy AF. So dive in and enjoy!

Here are some classic Chicago eats you can’t leave without trying. 

• Deep Dish: Chicago is known around the world for its crispy, buttery-crusted pizza called deep dish. Cooked in a deep pan, this pizza is a pie with thick layers of mozzarella and doused in tomato sauce. You’ll find Lou Malnati’s in neighborhoods throughout the city, but for a one-of-a-kind deep-dish experience, head to Chicago Pizza and Oven Grinder Co. for a bread bowl filled with cheese and sauce and flipped upside down on your plate. 
• Eat an Italian Beef: Definitely don’t make this cuisine your date night spot: the grease and oil from the spicy giardiniera, a relish made from pickled vegetables, oozes out of the sliced beef and bread and most likely all over you. Locals love to eat this filling sandwich from places like Portillo’s and Al’s #1 Italian Beef.
• Eat a Chicago Dog: There are many things Chicagoans are passionate about, and one of them is what makes a good hot dog. For this city, it’s a poppy seed bun with a Vienna beef dog topped with relish, tomato, onions, a pickle spear, celery salt, pepper and mustard. Don’t ever ask for ketchup! Hot dog stands are sprinkled through the city, but we suggest Chicago Hot Dog Hall of Fame inductee Duk’s Red Hots or Fatso’s.  

Short on time but big on food? Tick all of the must-eat Chicago foods off your list on a Chicago Food Tour, where you’ll sample all the essentials: hot dogs, Italian beef, and deep-dish pizza!

Try Cuisine from Every Corner of the World 

Chicago’s heavy manufacturing industry and jobs have attracted immigrants since its founding, which also meant an introduction to new foods.

You can find everything from Polish home cooking to Lithuanian bars, and many immigrant groups have their own enclaves, like the South Asian Devon Street in Rogers Park or the Vietnamese Argyle Street in Uptown.

Here are a couple of Chicago food experiences that will warm you up on a chilly day: 

• Try a flaky handheld pie in Chicago’s unofficial “Empanada Alley”: Lakeview’s Southport Avenue has become the city’s unofficial empanada alley. You’ll find many versions of Latin America’s favorite handheld staple. Start at Cafe Tola for the mouthwatering Mexican lechon empanada, then cross the street for Argentine-style empanadas at 5411. The ham and cheese or beef empanadas are classic, but the bacon, date, and goat cheese is a stunning combination of flavors. Finish off with authentic Argentina empanadas at El Mercadito. If you’re still hungry, indulge in an Argentina Asado at the BYOB Tango Sur, which features live music. Pair your food crawl with a movie at the 1920s-era Music Box Theatre on the same street. 
• Order Chinese in Chicago’s bustling Chinatown: This section of town is full of history and great restaurants. Make sure you come hungry to Happy Lamb, an all-you-can-eat hot pot restaurant with spicy and tangy broth, dozens of meat varieties and rich egg custard buns. If you want to taste a bit of everything this neighborhood has to offer, try a 2.5-hour food tour. 
• Eat Ethiopian in Chicago’s North Side: houses arguably the most famous Ethiopian restaurant in Chicago, Demera. Order a messob, or combination platter, of meats, vegetables, and sauces for an authentic taste of Ethiopia.

Sip Cocktails at a Swanky Bar—or Dive Bar

Chicagoans seem to love in equal parts their glitzy nights out and their hole-in-the-wall neighborhood pubs. To get a true sense of Chicago you should drink at both. 

Plus, you’re gonna be cold. So as soon as the sun goes down (even if it’s not quite 5pm yet) head to one of these bars to get a nice, warming-from-the-inside drink:

• Cindy’s: This rooftop bar at the top of the Loop’s historic Chicago Athletic Association Hotel has towering views of Lake Michigan and Millenium Park’s Cloud Gate. The best part? You can stay snug and warm and enjoy the views from inside their floor-to-ceiling glass walls. 
• Bordel: This West Town bar is famous for its punch served in tea sets and eclectic selection of entertainment harkening Paris’s belle epoque. Expect fire dancers, burlesque, and even live Flamenco guitar. 
• Rainbo Club: This dimly lit dive bar just south of Wicker Park boasts virtually unchanged 1940s decor, with red leather stools, booths, and a horseshoe-shaped bar. Take a photo in the cash-only photo booth and order a Chicago handshake for a truly authentic experience—an Old Style Beer with a shot of our notoriously harsh, bitter liquor malört. If you haven’t tried the deep dish yet, you’ll want to the day after drinking that. 

Honor Chicago’s Black History

Though there was already a small African American population at the turn of the century, Chicago was one of the Northern cities that received some of the millions of African Americans who migrated from the south in the 20th century during The Great Migration.

Often compared to Harlem, the newly-formed community in Bronzeville produced some of the country’s most famous doctors, musicians, and artists. Here are some ways to honor their contributions and learn about African American history in Chicago:

• Venture to Washington Park to visit The DuSable Museum of African American history, the oldest independent African American museum in the country. Housed in a turn-of-the-century building designed by renowned architect Daniel Burham, you’ll be amazed at the art, historical memorabilia, and special collections at this site. You’ll learn of Chicago’s most influential figures like the first Black mayor Harold Washington and the lasting legacy of the tragic 1919 race riots.  
• Check out the Bronzeville Walk of Fame, which tells the story of Chicago’s trailblazing African Americans and their contributions across ten blocks with commemorative bronze plaques on medians, sidewalks, and crosswalks. Learn about African Americans including journalist and human rights activist Ida B. Wells and poet Gwendolyn Brooks. 
• Admire art at the South Side Community Arts Center, a Chicago Historic Landmark long-standing community hub celebrating African American arts since 1940. Come in and check out art exhibits, and learn more about African American history in Chicago!

Laugh the Night Away at an Improv or Comedy Show

Chicago is the city where many famous comedians found their voices and launched their careers! There are dozens of other places to see the up-and-coming Chicago talent. 

• The Second City: The most famous place to see comedy is Old Town’s The Second City, with a rotating selection of pee-your-pants shows of varying themes. Comedians like Amy Sedaris, Debra Downings, Tina Fey and Amy Poehler got their starts here, so you know it’s gonna be some good sh*t! 
• The iO Theater: There’s never a dull moment with the wild improv actors at The iO Theater’s Improvised Shakespeare Company shows. Inventing a plot in the moment fully in old English, these actors take cues from the audience and sometimes can barely make it out without crying from laughter. 
• The Annoyance: Lakeview’s The Annoyance has evening and late-night improv shows in a casual setting. It also touts that it is “Home of the longest running musical in Chicago,” Co-ed Prison Sl**s, so I mean, you can’t go wrong obviously.
• Laugh Factory: Boystown’s Laugh Factory is best for those who cringe at improv—they hold mainly stand-up shows from local and national celebrities.

Spend a Day at the Museums

There are hundreds of wonderfully curated museums in Chicago that garnered international attention and house important arts, culture, and history of the city.

And they are the perfect place to pop into after walking the snowy streets and admiring the Christmas lights! These Chicago museums will warm you up and inspire you:

• The Museum Campus: The 57-acre museum park (called “The Museum Campus”) along Lake Michigan gets a lot of wind in the winter months, but the beautiful turn-of-the-century buildings that house the museums are worth checking out. There, you’ll find the Field Museum, Adler Planetarium, Shedd Aquarium, so you can dream of tropical waters on a chilly day.
• The National Museum of Mexican Art: Along the streets of Pilsen, the heart of the Mexican-American community of Chicago, visit the National Museum of Mexican Art for an extensive collection of textiles, folk art, sculptures and artifacts that showcase Indigenous and Mexican history and the Mexican-American experience of Chicago. Spend time after the museum roaming the streets full of beautiful murals, protest art, shops and restaurants. 
• The Swedish-American Museum: Though Chicago is most commonly recognized for its Polish, Irish, and Italian heritage, the Swedish-American Museum in Andersonville is dedicated to telling the story of a lesser-known European migrant group who settled here. See Swedish artifacts like traditional furniture and clothing and learn about their immigration to Chicago.

Admire Chicago’s Architecture

When Chicago burned to the ground in 1871, the city officials decided to take a chance at something new. This legacy has lasted through the decades and fostered a sense of innovation in the city.

Here’s where you can learn about Chicago architecture: 

• Starting with a visit to the Loop’s Chicago Architecture Center, learn about some of the city’s most interesting architectural wonders and how Chicago’s inventive architecture figured out to make the world’s most famous skyscrapers. 
• Take an architecture tour: If you want to continue admiring the Loop’s skyscrapers and combine food and architecture into one activity, this 5-hour long tour has both! You’ll start at the famous Chicago Theater, and visit other iconic places like City Hall and Michicgan Ave, all while enjoying popcorn, hot dogs, pizza, and chocolate. Basically the best of both worlds!
• Take a Frank Lloyd Wright tour: If you’re ready to see what other architectural gems are hidden beyond the Loop, you can admire the innovative architecture of Frank Lloyd Wright, who designed over 1,000 structures over his long career. Though he’s most famous for designing New York City’s Guggenheim Museum, head to the Western Suburb Oak Park for a tour of his iconic buildings in this neighborhood.

Listen to Live Music 

The city that brought you house music (yes, that was Chicago, not Europe!), electric blues, groundbreaking jazz and gospel music has no shortage of live music venues to satisfy any musical style. There’s nothing cozier than a bustling club, a cocktail, dim lights and a warm sweater as you’re swaying to smooth jazz. 

Pick the music that speaks to you:

• Head to a jazz bar: Once a hangout of Al Capone, Uptown’s cash-only bar The Green Mill is one of the best spots in the city for live jazz every night of the week. It’s extremely popular and they don’t take reservations, so get there early to snag your spot. 
• Sing the Blues: Since 1968 Lincoln Park’s Kingston Mines has been giving Chicago the gift of talented Blues music. Sip your drink and snack on classic bar food and Southern favorites as you immerse yourself in the music that traveled all the way up from Memphis, Tennessee and found a home in the North.
• See a band before they sell out: Empty Bottle is a grungy, local spot in West Town that has nightly shows and features famous indie bands and up-and-coming musicians. You’ll find cheap drinks, a casual atmosphere and lots of space to jam out in the eclectic space. 

Where to Stay in Chicago

Though most tourists opt to stay in the Loop, The West Town area—comprising Wicker Park, Ukrainian Village, and East Village—is an ideal location for affordable accommodation to live like a local while also indulging in some of the city’s best bars, restaurants, boutiques, shops, and colorful street art.

Once known as “Polish Downtown,” this centrally-located neighborhood is just a 20-minute train ride from downtown has changed drastically since MTV filmed “The Real World” here in 2001. The location is centrally located and hotspots like West Loop, Logan Square, and Lincoln Park are only a short bus or train ride away. 

• Boutique Hotel: Once the only skyscraper outside of the Loop, The Robey offers stunning 180-degree views of the diagonal Milwaukee Avenue and downtown. Located on one of Wicker Park’s most popular intersections and just a few feet from the Damen Blue Line El station, this art deco-style tower gets you closest to the trendiest bars, restaurants, and nightlife. 

• Bed & Breakfast: Situated just south of busy Milwaukee Avenue on a charming tree-lined street, the Wicker Park Inn has nine elegantly decorated suites. Housed in an 1890s row house, this bed and breakfast provides guests with a cozy common area and light breakfast. 

• Vacation Rental: This spacious West Town loft with exposed brick, modern art, and outdoor space has all of the comforts and amenities to be your homebase for exploring the city. It’s close to public transportation and groceries and puts you in the heart of daily life in the city. 

What to Pack for Chicago in the winter

Locals and tourists alike can brave any unpredictable weather with the best tool: layering. Since winter could feel either like a sunny spring day or the worst arctic snowstorm in history, strategic layers will ensure that you stay dry (or dry quickly with the right fabric), protected from the powerful wind gusts and still able to explore comfortably.

Ever heard that saying, “there’s no such thing as bad weather, just bad clothing?”Well, you’re about to discover exactly what that means! Don’t worry, we’ve got all the tips to keep you warm and toasty on your trip.

We recommend wearing a merino wool base layer underneath your clothing every day during your trip – that means that the layer closest to your skin should all be made from merino wool. If wool isn’t your thing, wear an equally insulating textile, like hemp or silk. Avoid non-insulating fabrics like cotton, and remember that natural fibers are pretty much always better than manmade textiles like polyester.

After your base layer, you’ll need to add on at least 1 additional layer before your outerwear, like a pair of pants and a sweater. On REALLY cold days, where the temperatures are below 10 degrees, we recommend adding on another base layer before your clothing layer & outerwear. For more winter travel packing tips, head over to our Cold Weather Packing Guide.

• Warm Winter Coat: Your jacket is arguably the most important thing you’ll pack for your trip other than your shoes. It has a big job – namely, keeping you warm but not sweaty, allowing you to actually move your arms, and letting you explore for hours without feeling heavy or restrictive. Plus, it’s gonna be in almost all of your photos! I love this this cozy fleece-lined coat, and Jeremy wears a wool-blend coat similar to this one and this one. I also highly recommend bringing a cozy Packable Down Jacket – it packs down into nothing and adds a super-warm extra layer when you need it!
• Warm Walking Boots: We recommend boots that can withstand ice or snow, are weatherproof and waterproof, and are comfortable enough to walk in for HOURS. Sounds darn near impossible, right? Well, it’s not. We’ve found the best boots for winter, and we’re OBSESSED with them (and yes, we both have the same ones. Because we’re kinda gross like that). They’re cute, they’re insanely comfortable, they’re waterproof leather and lined with shearling to keep your toes toasty warm, and they’re extremely lightweight and foldable so you can stuff them in your bag when you travel. Oh, and they have thin and flexible soles that let your feet function as if you were walking around in the cold completely barefoot!  Note: you might find yourself in need of some calf strengthening if you’re not used to barefoot-style soles. We can’t recommend these boots enough. They’re made to last and they’re worth every cent. Here are my boots and Jeremy’s boots. You can read more about them in our round-up of our favorite travel shoes for women or for men.
• Merino Wool Base Layer Leggings: These super comfy 100% wool leggings function just like long underwear. They’re made of soft, super-luxurious wool and make your legs feel like they’re being hugged by an extremely soft sheep. Jeremy has this pair. You’ll need to wear these underneath your pants every day during your trip.
• Merino Wool Base Layer Undershirt: Laying is crucial when it’s this cold, and you’ll need to start with a layer of insulation on top and bottom. Although sometimes I can get away with a short sleeved or even sleeveless undershirt, on very cold days we both need to wear a layer of long-sleeved wool. This is mine and this is Jeremy’s.
• Wool Socks: Good socks are a must for your snow boots. Frozen toes are definitely a thing when you’re spending time admiring Chicago’s beautiful architecture or ice skating. Make sure you don’t just have run-of-the-mill acrylic socks – they won’t keep your feet warm while you’re out in the snow! Instead, bring socks that are primarily made of soft, heat-regulating wool, like these or these. I recommend 2 layers of socks – no more, no less.
• Warm hat or headband: Even on the relatively “warm” winter days, the wind turns the toughest ears bright red, so this is a must for any traveler. You can go practical or cute on this one—for many locals the most important thing is staying warm. 
• Waterproof gloves: Just like a hat, no sane Chicagoan would leave home without protecting their precious hands. Waterproof gloves are a must, and it’s nice to have touchscreen winter gloves so you don’t have to remove yours to look up directions or take a photo!
• Thermal leggings: On really cold days, one layer doesn’t cut it. Bring a pair of fleece-lined thermal leggings to fit under your jeans. Speaking of…
• Travel Jeans:  My favorite travel jeans have 6 POCKETS. 6!! And 2 of them are zipped and hidden inside other pockets, for extra pickpocket protection. They’re super stretchy and buttery soft, dry quickly even after walking through the snow, and roomy enough to layer over an insulating base layer (or two). They’re cozy enough to wear on a plane, stretchy enough to accommodate that 5 extra pounds of holiday weight I always seem to bring back home with me, and they’re super cute! We’re both obsessed. You can get a pair of men’s or women’s jeans on the Aviator USA website.
• Sweaters: If you know you’ll be heading indoors, bring a cozy, soft sweater that will go great with your snow-soaked boots. 
• Scarves: With so many layers it can be hard to feel fashionable, but a bright accent scarf will cheer up any cloudy day or monotone outfit. Keep the fabric merino wool so that any stray snow won’t soak into the scarf and make the rest of your day miserable. 
• Warm Flannel Shirt: I’m in LOVE with the MerinoLux flannel button-down from Royal Robbins. It’s stretchy, it’s cozy, it’s blended with merino wool (yassss) and most importantly, it’s warm AF and super breathable. It’s also wrinkle-resistant, odor-resistant, and moisture-wicking, and has a hidden zip pocket – so basically everything you could ever ask for in a flannel shirt. I’ve been searching for the perfect flannel for YEARS (you know, like one that didn’t give me that annoying button-down boob gap and allowed me to actually cross my arms) and this is The One. I love it! Here’s mine and Jeremy’s.

For more winter travel packing tips, head over to our Cold Weather Packing Guide!

About the Writer: Allison Yates is a Chicago-based writer and the creator of Read & Run Chicago, the city’s first and only running experience built by stories. You can find her on Instagram.

Which one of these things to do in Chicago in winter are you most excited to try first? Is it tasting Chicago’s famous food, or exploring the Christmas Market? Or are we just hungry? Let us know in the comments below!

Psst: Looking for more winter travel ideas? …. We have a few other posts to check out!

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