BEST Things to Do in Chicago in the Winter 2023/2024 (From a Local!)

Wondering what there is to do in Chicago this winter? Below are the best things to do in Chicago during the winter from a local – whether looking for fun outdoor winter activities or the best Chicago indoor attractions.

I suggest bookmarking this blog post as I plan to update it regularly with new events and activities.

Chicago in the Winter

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Is it Worth Visiting Chicago During the Winter?

For out of town visitors, Chicago has a bad reputation for being cold, snowy and windy in the winter but that is not always true. Some years winters can be mild and even on a colder winter season many days can randomly be mild or warm. You might get lucky and get pleasant temperatures especially if you are visiting in the beginning or end of winter.

Winter weather can start as early as November and end as late as March or early April,  However, the months that typically have the worst weather (cold and snow) are January and February.

If you can brave the potentially bad weather, Chicago is a great place to visit in the winter. In the beginning of winter, you can enjoy the many holiday events and activities that take place in Chicago until the first week in January. The rest of winter is considered low season for tourism in Chicago, which means lower hotel prices and fewer crowds at popular attractions. There is no shortage of indoors things to do in Chicago from museums, great restaurants, tall buildings, shopping, theater, comedy clubs and more!

If you end up loving Chicago (most people do), you can always return when the weather is warmer for Chicago outdoor activities (such as the river cruises) you can enjoy year round.

What to Pack for Chicago in the Winter

Layers are key because the temperature can vary greatly (from below freezing to more than 60 Fahrenheit). Here are some things to pack if you are visiting Chicago in the winter for the first time:

• Winter coat – I recommend a longer coat with a hoodie to keep you warm
• Knit hat
• Scarf
• Gloves – Thin touchscreen gloves are best so you can use your smartphone without having to take them off
• Boots – Boots are a must if it snows but some people like to wear them even if there is no snow because they are warmer. Make sure your boots are water resistant with good traction.
• Reusable water bottle
• External battery for your phone – To recharge your phone’s battery when you are outdoors

Where to Stay in Chicago During the Winter

If you are visiting Chicago in the winter, it is even more important to stay somewhere centrally located so you don’t have to walk very far while sightseeing or spend money on ride sharing. I recommend these Chicago hotels for winter – they are not only centrally located but many also offer winter attractions and activities like heated rooftops and even curling.

The Peninsula Chicago.  The Peninsula Chicago is a 5 star hotel with a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. This is the only hotel in Chicago with a seasonal skating rink. Other hotel amenities include a world renown spa and a half-Olympic length swimming pool. Click here to see the latest prices and click here to read reviews.

Gwen Hotel Chicago.  The Gwen Hotel Chicago is conveniently located off the Magnificent Mile and is connected to The Shops at North Bridge, which provides guests with enclosed access to shopping. The hotel was ranked #1 in Chicago and #8 in the world according to Condé Nast The Best Hotels in the World: 2021 Readers’ Choice Awards. It has an outdoor winter rooftop with fire pits and heaters as well as outdoor curling and igloos. Click here to see the latest prices and click here to read reviews.

LondonHouse Chicago, Curio Collection by Hilton.  LondonHouse Chicago, Curio Collection by Hilton is located on the iconic Chicago River, on the corner of Wacker Drive and Michigan Avenue, just minutes away from Millennium Park and the city’s theater and business districts. Many of their rooms as well as their tri-level rooftop bar have amazing views of the Chicago River. Click here to see the latest prices and click here to read reviews.

Chicago Athletic Association Hotel.  Chicago Athletic Association Hotel is a unique boutique hotel conveniently located right across The Bean and Millennium Park. It is a short walking distance to two ice skating rinks as well as The Art Institute of Chicago. The hotel has several bars & restaurants including Cindy’s, the popular rooftop restaurant and bar which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. Families will enjoy spending time in their Game room where you can play billiards, shuffleboard, foosball, and other games for free. Click here to see the latest prices and click here to read reviews.

Things to Do in Chicago in the Winter

Below are the top things to do in Chicago this winter. You will find something for both adults and families with kids to do in December, January, February and early March in the city and suburbs.

Go Outdoor Ice Skating

There are several places to go outdoor ice skating in Chicago during the winter. Skating rinks in Chicago are usually open mid-November until early March (weather permitting).

One of the best and picture perfect spots to go ice skating is at the McCormick Tribune Ice Rink in Millennium Park right in front of The Bean. Admission is free, but online ticketed reservations are required.

Another ice skating rink with great skyline views is the skating ribbon at Maggie Daley Park located next to Millennium Park. The skating ribbon has a path twice the length of a lap around a traditional skating rink. Reservations are strongly encouraged. See the official website for hours and prices.

Join a Food Tour

Winter is a great time try some of the food that Chicago is known for. If your time in Chicago is short or you want to try a variety of dishes, consider a food tour like this Chicago favorites tasting tour. If you have a sweet tooth, you might like this underground donut tour.

Take a Holiday Tour

If you are visiting Chicago early winter, there are a few tours that focus on Chicago’s holiday attractions:

Festive Food & Walking Tour
Seasonal Stroll Walking Tour of Holiday Attractions

See the Giant City of Chicago Christmas Tree

The offical City of Chicago Christmas Tree can be found at Millennium Park from mid-November through the first week of January.

Where: Millennium Park near the intersection of Michigan Avenue & Washington Street.

Cost:  Free.

Admire Famous Works at The Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

When: Hours are Monday and Thursday–Sunday from 11 a.m.– 6 p.m. Closed on Tuesdays & Wednesdays.

Where: 111 S Michigan Ave, Chicago, IL 60603

Cost:  $25 for adults, $19 for seniors, students and teens (14-17); members and children under 14 are always free.

Enjoy Warm Temperatures at the Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.

Where: 300 N. Central Park Ave., Chicago, IL 60624

Hours: Wednesday 10am-8pm; Thursday – Sunday 10am-5pm; Closed Monday and Tuesday. Visitors are encouraged to make a reservation online in advance.

Cost: FREE (suggested donation)

See Flowers Inside the Lincoln Park Conservatory

Lincoln Park Conservatory is a smaller conservatory but closer to other tourist attractions. It is always green and lush year round, offering visitors a tropical experience within its four display houses: Palm House, Fern Room, Orchid House and Show House.

Hours: Wednesday through Sunday from 10:00 am – 3:00 pm (last entry at 2:00 pm). Timed entry reservation is required.

Where: 2391 N. Stockton Drive, Chicago, IL 60614

Cost: Admission is free, but registrations are required.

Visit the Field Museum

The Field Museum is one of the largest natural history museums in the world with more than 40 million specimens and artifacts. Inside the museum you will see Maximo, the Titanosaur, the largest dinosaur that ever lived. (Click here to purchase an Early Access VIP Tour if you want to avoid crowds and lines).

Hours: Open daily 9am to 5pm (last admission at 4pm)

Where: Chicago’s Museum Campus, 1400 S Lake Shore Dr, Chicago, IL 60605 (detailed directions and parking information is available here)

Enjoy the Views from 360 CHICAGO Observation Deck

360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan (which might be frozen).

(Click here to buy a skip the line ticket).

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

Visit the Shedd Aquarium

Visit the Shedd Aquarium, one of the world’s largest indoor aquariums, for unforgettable encounters with aquatic animals including belugas and bluegills, stingrays, sturgeons and more.

Where: 1200 S. Lake Shore Drive, Chicago, IL 60605 (detailed directions and parking information is available here)

Hours: Open 9 am – 5 pm. Advance purchase of timed tickets is required.

Cost: Price varies depending on day. Admission is free for Illinois residents on select dates this winter (must be reserved online in advance).

Tip:  If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Visit the new Museum of Ice Cream

Museum of Ice Cream is Chicago’s newest attraction. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles.

Where: Tribune Tower, 435 North Michigan Ave, Chicago, IL 60611

Cost: You can see full prices and purchase tickets in advance here.

Visit the Color Factory

Color Factory is a new interactive art museum located on the lower level of Willis Tower. Named one of the 22 Best New Experiences in the World in 2022 by Time Out, the Color Factory is a sensory celebration of color, with interactive installations, immersive rooms and carefully curated moments inspired by the city of Chicago including its signature ball pit and confetti room.

Hours: Hours vary, advance tickets are required.

Where: Willis Tower, 320 W Jackson Blvd, Chicago, IL 60606

Cost: Tickets start at $28 per person.