Although known for its cold weather, there are plenty of things to do in Chicago in the winter that are worth checking out that won’t freeze you. Whether you’re travelling for the holidays or looking for seasonal events, the Windy City is beautiful during this time of year.
From snowy activities to indoor festivals and family-friendly attractions, here’s how to explore Chicago in wintertime while staying warm.
Explore the Top 10 Things to Do in Chicago in the Winter: What to Do During the Cold Season
Below are the top 10 things to do in Chicago in the winter, with public transit directions to navigate the big city easily.
1. Experience the Winter Wonderfest at Navy Pier
Source: Navy Pier
While a waterfront destination may seem too cold in Chicago during winter, Navy Pier’s annual Winter Wonderfest is an indoor holiday experience. Running from December to early January, it’s packed with festive fun activities perfect for all ages.
Some of Winter Wonderfest’s top attractions are:
•Capturing photo memories at the 42-foot holiday tree and larger-than-life decorations throughout the venueÂ
•Going ice skating while listening to live music and special performances from the Winter Wonder Stage
•Enjoying the fun to thrill-seeking rides, including the nearly 200-foot iconic Centennial Ferris wheel, the Cliffhanger, and electric bumper cars
•Eating food and drinks from local vendors, like stuffed pizza, caramel cupcakes, and holiday martinis
General admission costs $25 or $35 for ice skating, and all tickets include one ride on the Centennial Ferris Wheel.Â
Navy Pier is in Chicago’s Streeterville neighborhood and located at 600 E. Grand Ave. There are several public transit routes available, including water taxis, bike shares, and two onsite parking garages. The Millennium Metra is the nearest train station, which is about a 20-minute walk via the Metra Electric (ME) and South Shore Line (SSL) Lines. You can also transfer to CTA Bus #124 to take you directly to the pier, with five daily bus lines to Navy Pier.
2. Go to the Ice Skating Ribbon at Maggie Daley Park
Source: Time Out
You’ve likely been ice skating before. But Maggie Daley Park’s ice skating ribbon is truly a unique experience and one of the most popular Chicago attractions in the winter. Unlike traditional ice rinks, it’s immersive outdoor ice-covered paths that circle skyscrapers, themed play spaces, and decorated pine trees.
You can go ice skating during the day or at night, where the winter wonderland comes to life even more. The seasonal schedule runs from mid-November to early March, with figure and hockey skate rentals available for different skill levels at $21 per person. We recommend making reservations as slots can fill up quickly for parties of up to 10.
Maggie Daley Park is in downtown Chicago, right next to Millennium Park at 337 E Randolph St. The Millennium train station is a 10-minute walk via the ME and SSL lines. The Randolph & Field Blvd bus stop is also less than a five-minute walk via Bus 60.
3. Soak in Stunning Views of Frozen Lake Michigan on the Lakefront Trail
If you’re searching for free things to do in Chicago in the winter, the Lakefront Trail is a stunning winter landscape worth seeing. It’s an 18.5-mile shoreline trail along Lake Michigan where it’s frozen during this time of year, with surrounding snow-covered trees, lakeside beaches, and cityscape views. We recommend layering your clothes, as the wind chill can get cold. However, there are plenty of stops along the way to warm up, like local restaurants, cafes, and museums.
The Lakefront Trail is in Chicago’s Lakeview neighborhood, stretching from Fullerton Ave on the south to Irving Park Rd. The Sheridan train station is less than a 15-minute walk via the Red Line to Irving Park Rd.
4. Take a Dinner Cruise Date on Lake Michigan
Source: City Cruises
Looking for romantic things to do in Chicago in the winter? Take your loved one on a luxury dinner cruise on Lake Michigan. You can dine on the water while staying warm inside a climate-controlled glass-enclosed yacht. There are delicious chef-curated meals where you’ll eat alongside breathtaking views of the lake and city skyline for 2.5 hours. The yacht also features open-air decks for closer views, a bar serving craft cocktails, and live DJ entertainment that will elevate your date to the next level.Â
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Hosted by City Cruises, they’re located on the Navy Pier at 600 E Grand Ave. The Millennium train station is about a 20-minute walk via the ME and SSL Lines, or you can transfer to CTA Bus #124 to take you directly to the pier.
5. Attend a Wine Festival at the Field Museum
Source: Uncorked Wine Festivals
The Uncorked Chicago Wine Festival isn’t your ordinary wine festival. It takes place at the Field Museum in early March, where you can sip over 100 global wines, champagnes, and mocktails alongside amazing exhibits. These include historical collections of fossils, meteorites, and two gigantic dinosaur skeletons–Sue the T.Rex (the world’s largest) and Máximo the titanosaur.
The 21+ event also has a live DJ, a newly added Zero Proof lounge, and an expanded downstairs VIP experience for exclusive access to premium wine brands.Â
There are three ticket types available:
•General Admission: $70 per person, starting at 8:00 pm to 11:00 pm, with three hours of museum access
•Early Admission: $85 per person, starting at 7:00 pm with four hours of museum access and a smaller capacity during the first hour
•VIP Admission: $110 per person, starting at 7:00 pm with four hours of museum access, shorter tasting lines, an exclusive VIP area with additional premium wineries, and a $30 food voucher
The Field Museum is on Museum Campus in the South Loop neighborhood at 1400 S Lake Shore Dr. The Museum Campus/11th St train station is a nine-minute walk via the ME or SSL Lines. The Roosevelt & Michigan/Indiana bus stop is a 10-minute walk via Bus 12 or 146.Â
There is also onsite parking and two parking garages nearby at Soldier Field North Garage and Soldier Field East Museum Lot.
6. Warm Up Inside at a Comedy Club
Chicago has been a historical hub of the comedy scene and a great way to escape the cold indoors. With several comedy clubs where many celebrities started their careers, like Stephen Colbert and Tina Fey, there are various types of comedy to enjoy throughout the city.
Some of the top comedy venues in Chicago are:
•The Second City: The oldest improv theatre troupe in Chicago, with two stages, weekly daytime and nighttime shows, and open mic nights. It’s located in the Lincoln Park neighborhood.
•Laugh Factory: A weekly standup venue with VIP lounges on a balcony, open mic nights, and food/beverages. It’s located in the Lakeview neighborhood.
•Annoyance Theatre: The longest-running performance space, featuring improv and sketch comedy, full-length plays, cabaret, and musicals with two stages. It’s also located in the Lakeview neighborhood, down the street from the Laugh Factory.
These venues vary in size from large to intimate shows, each offering a bar, food, and beverages while watching the show.
7. Sip Cocktails Inside an Igloo at Kennedy Rooftop
Source: Kennedy Rooftop
Embrace Chicago in the winter at Kenny Rooftop’s bar. But don’t worry, it’s winter-proofed so you can stay warm inside a cozy, illuminating igloo while soaking in the Chicago skyline views. Extra-large igloos were also newly added, seating up to 12 guests for your friends or to celebrate special occasions.
You can drink toasty craft cocktails like spicy tamarind margaritas, rye old fashioneds, and a wide selection of wines. They also have a food menu, featuring mushroom pesto flatbreads, harissa chicken kabobs, and a Reese’s peanut butter cup skillet with vanilla ice cream.
Kennedy Rooftop is located in the Wicker Park neighborhood at 1551 W North Ave, Ashland. The Clybourn train station is a 10-minute walk via the Union Pacific-North (UP-N) and the Union Pacific Northwest (UP-NW) Lines. The North Ave & Ashland bus stop is also only a one-minute walk via Bus 72.Â
8. Rent a Hot Tub Boat Along the Chicago River
Source: Chicago Boat Company
On the hunt for unique group Chicago winter activities? Grab up to six friends to rent a hot tub boat along the Chicago River during the day. It’s a one-of-a-kind experience where you can drink and listen to music from a built-in Bluetooth speaker on the water. However, you must sign a responsible party waiver to ensure safe drinking practices.
While you’ll be in a swimsuit, the hot tub with hats and ear muffs will surely keep you warm while floating. There’s also a waterproof phone case and floating cup holders to store your devices and drinks. It’s a 90-minute winter-boating experience, but guests can be 13 and older if you want to bring family, too.
Hosted by the Chicago Boat Company, they’re located in the River North neighborhood at 300 N State St, Suite EE. The State/Lake train station is a five-minute walk with five routes available, including the Brown, Green, and Orange Lines. The State & Marina City bus stop is only a minute walk away with four routes available, including Bus 146, 151, and 125.
9. Go Sledding at Soldier Field
What good is finding winter activities in Chicago without sledding? Soldier Field may be a sports stadium, home to the Chicago Bears, but its nearby 220-foot hill is what attracts people to come sledding. And if there isn’t enough snow, the Chicago Park District even makes snow so you can still sled throughout the winter season. It’s also free to the public!Â
The sled hill is across the street from Soldier Field in the South Loop neighborhood at 1410 S Museum Campus Dr. The closest public transit route is the 18th St train station, a 10-minute walk via the ME Line.
10. See the Snowy Animals for Free at Lincoln Park Zoo
Source: Lincoln Park Zoo
If you want to find family-friendly winter Chicago activities, the Lincoln Park Zoo is a great place to take the kids—for free, too! The zoo is open year-round with free daily admissions and is less packed during this time of year.Â
What makes visiting in wintertime special is that you can find their cold-weather animals, including polar bears, red pandas, and snow monkeys (Japanese macaques), outside in the snow. There are also winter learning programs, like seal training and feeding, for an additional ticketed experience. But don’t worry, the zoo has indoor exhibits and buildings, like the reptile house and dining, to take a break from the cold while still enjoying everything it has to offer.Â
The Lincoln Park Zoo is in the Lincoln Park neighborhood at 2100 N. Clark St. The closest public transit route is the Stockton & Webster bus stop, a one-minute walk via Bus 151 or 156. The Sedgwick train station is about a 20-minute walk via the Brown or Purple Lines.
Call Chicago Your New Apartment Home This Winter Season
Now that you know what to do in Chicago in the winter, you can live near its many attractions with a luxury apartment home. At TLC Management Co., we have over 30 properties in the Chicagoland area, with the local expertise to find you the best place to rent.Â
Our apartments offer unique and convenient winter-proof amenities for all lifestyles, including:
•Smart thermostats and self-cleaning electric ranges in newly renovated units
•Frameless glass shower doors, in-unit laundry, and floor-to-ceiling windows with solar shades
•Pet-friendly communities, sun decks with fire pits, and additional storage availableÂ
Ready to make your move this winter?
Browse our Chicago apartment properties or contact us at info@chicagorentals.com to schedule a tour today!
