Wintertime is definitely the offseason in Chicago. Temperatures can drop to below freezing and buckets of snow cover the city throughout the winter season. However, just because it is cold and snowy does not mean you should not visit Chicago during this time. There are plenty of things to do in Chicago in the winter that can keep visitors out of the cold, and a ton of festive ways to celebrate Christmas in Chicago!
Need help figuring out what to pack? Check out my packing list for winter destinations.
Disclaimer: Special thanks to the Chicago Tourism Board and companies for hosting me at several excursions and restaurants on my trip to Chicago! As always, all thoughts and opinions remain my own. This post contains affiliate links. I may earn a commission at no cost to you!
Table of Contents
Where to Stay
Many of the main sites are in Downtown Chicago which includes the River North and Millennium Mile areas. If possible, these are the most ideal areas to stay in. By visiting Chicago in the winter, you are able to score some fantastic deals on hotels.
This past trip, I scored a Priceline Express Deal For The Westin Michigan Avenue, located right on the Magnificent Mile, for $86/night! On another trip, I managed to find the Hampton Inn Downtown for $55/night. Make sure to book early to find the best deals. If you are looking for an apartment make sure to check out Airbnb for some great options.
Transportation
The cheapest way to get around Chicago is by taking the ‘L’ Train. The ‘L’ is $2.50/ride or you can buy a day pass for $10, a 3-day pass for $20, or a 7-day pass for $28. If you have a larger group, it is also convenient to use Uber/Lyft to get around the city, especially when it is cold.
Things to Do In Chicago in the Winter
Chicago in the wintertime can be freezing. However, there are a ton of indoor activities to keep you out of the cold! There are also some unique things to do in Chicago in the winter. I love visiting Chicago in the wintertime since there are fewer crowds and you get a completely different experience than going in the summertime.
GoCity Pass
GoCity offers a ton of different sightseeing passes for cities around the world. These passes allow you to visit the best of each city for one low price, rather than paying individually for each attraction. I have used it in several cities around the world and would recommend getting a GoCity pass! Check out the options for the Chicago GoCity pass here.
The Art Institute of Chicago
Cost: $25 General Admission
Hours: Open Daily from 10:30am to 5pm and until 8pm on Wednesday, Thursday, and Friday.
One of my favorite museums in the world is the Art Institute of Chicago. This museum, founded in 1879, is one of the oldest art museums in the United States and contains over 300,000 works of art. Make sure not to miss Georges Seurat’s “A Sunday on La Grande Jatte” and Grant Wood’s “American Gothic.” My personal favorite is the “Picture of Dorian Gray.” Plan to spend a couple of hours perusing the art collections. I found all of the museum staff to be friendly and knowledgeable about the museum.
Auditorium Theater
Cost: $12 General Admission
Hours: Varies depending on the schedule of the shows. Check the website for more information.
This hour-long tour of the Auditorium Theater is a must for any theater lover. Not only did you get to learn about the history of the theater, I learned some unique facts too. The Auditorium Theater was the first major building to be built after the Chicago Fire and was worked on by Frank Lloyd Wright. In its early days, it contained a hotel, office spaces, a pharmacy, along with the theater. Present-day, it is part of Roosevelt University and is a host to a variety of shows, from Broadway Musicals to speakers like Ruth Bader Ginsberg. It is also registered as a National Historic Landmark. A tour of this theater is a really neat experience and the perfect way to escape the cold Chicago weather.
Chicago Architecture Center
Cost: $12 General Admission
Hours: 9:30am to 5pm.
The Chicago Architecture Center was originally established in 1966 as a small center that ran tours. The CAC offers about 85 walking, bus, bike, boat, and “L” train tours. In the summer of 2018, the center opened a larger facility that included a two-story museum dedicated to the architecture of Chicago. It is best known for its 3D printed model of Chicago, which is the largest 3D printed model of Chicago. It is made up of 4,250 3D printed buildings! The model is updated every 6 months with new buildings and also shows where all the potholes in the cities are.
The second floor of the center contains a rotating exhibit of models of famous buildings from all around the world. Right now, they have a model of the new building that is being built in Saudi Arabia. Once completed, it will be the tallest building in the world! Some of the models are 3D printed, and some are built by hand.
Their newest exhibit will open in April 2020 and is called “Energy Revolution: Creating Our Carbon-Free Future.” This exhibit will focus on how people can change their actions to help free the city of fossil fuels and move towards a carbon-free Chicago. Make sure to check it out next time you are in Chicago!
Chicago History Museum
Cost: $19 General Admission ($17 for Illinois Teachers)
Hours: Mon, Wed-Sat: 9:30am-4:30pm, Tues: 9:30am-9pm, Sun: 12pm-5pm
The Chicago History Museum is all about the history of Chicago from its founding. This museum was founded as the Chicago Historical Society in 1856 and is located in the Lincoln Park neighborhood. The original building burned down in the Great Chicago Fire of 1871 and many documents were lost. However, the museum rebuilt itself and gained access to a ton of new manuscripts in 1920. In 2006, the museum became known as the Chicago History Museum. Since then, it has become a popular place for people to learn about the history of Chicago.
The Field Museum
Cost: $26 General Admission
Hours: Open Daily 9am-5pm
The Field Museum is the Natural History Museum of Chicago. It is one of the largest natural history museums in the world. It contains a plethora of diverse exhibits from ancient cultures to scientific discoveries. My favorites areas are the dinosaur fossil area and the mummies. Make sure to check out Sue, the largest T-Rex species to have been discovered.
Goose Island Brewery Tour
Cost: $12 for a tour, $6 and up for pints
Hours: Wednesday/Thursday 12pm-8pm, Friday/Saturday 12pm-10pm, Sunday 12pm-6pm
Goose Island Brewery began as a brewpub in Lincoln Park, Chicago in 1988. Its beers are now sold all over the United States. If you are a beer lover, a stop at Goose Island Brewery for a tour is a must. Each tour is 45 minutes and it takes guests all over the facility, including the barrel aging warehouse across the street. Throughout the tour, guests also receive several samples of Goose Island beers. At the end of the tour, we received a beer of our choice and a souvenir pint glass to take home.
Millennium Park
Cost: Free to walk around and observe, $12-$14 if you need to rent skates.
Hours: Varies by attraction
Millennium Park is a public park in the middle of Chicago. It offers several attractions and a plethora of public art to view. The landmark of Millennium Park is “Cloud Gate” also known as “The Bean.” This public sculpture was created by Sir Anish Kapoor. Make sure to check out the reflections of the skyline in “The Bean.” Millennium Park also offers ice skating as one of the many things to do in Chicago in the winter. It is free to ice skate, but costs if you need to rent skates. The Art Institute of Chicago and the Chicago Cultural Center are some of the other attractions located inside the park.
Skydeck at the Willis Tower
Cost: $26 General Admission, but make sure to check Travelzoo or Groupon for Discount Tickets
Hours: March-September: 9am-10pm, October-February: Sunday-Friday, 10am to 8pm and Saturday, 9:30am-9pm
The Willis Tower (previously known as the Sears Tower), a 110-story skyscraper, was completed in 1973. It held the title of the tallest building in the world for 25 years. Present-day, visitors can ascend the building for amazing views of Chicago. Visitors can also opt for “The Ledge” experience, where a glass box extends out 4.3 feet from the Skydeck and you stand 1,353 feet in the air. Take the step out if you dare!
Go Shopping on the Magnificent Mile
Cost: Free (for window shopping)
Hours: Varies by store, but generally am-pm
The Magnificent Mile is the perfect place to start for any shopping lover. This mile-long street contains many of the world’s leading retail stores such as Macy’s, Nordstroms, Neiman Marcus as well as some smaller boutique stores. This street also contains a ton of restaurants and hotels. It is the perfect place to satisfy any of your shopping needs.
360 Chicago Observation Deck at the John Hancock Building
Cost: $22 General Admission, $5 for the TILT Experience, 25% off tickets during wintertime
Hours: 9am-11pm
The John Hancock Building was completed in 1969 and stands at 1,128 feet (100 stories) tall. This observation deck gives 360-degree views of Chicago and a great opportunity to take some pictures. If you are into thrills, add on tickets for TILT, which is an enclosed platform that tilts visitors over Michigan Ave. 360 Chicago offers different activities each day of the week, such as yoga, trivia, and happy hour.
Take a Food Tour with Chicago Food Planet
Cost: $50 and up (but check Groupon for sales)
Hours: Varies by tour. Check the website for more information.
When visiting a city, I love checking out the local food scene. Therefore, a food tour can be a fantastic way of learning about some of the local places. Chicago Food Planet offers 6 distinct food tours depending on your preference. I opted to do the Gateway to the West Loop Food Tour. This 3-hour tour took us to 5 different restaurants and each one was unique and delicious. Read more about the Gateway to the West Loop food tour we took here.
Walking Tour by Free Tours by Foot
Cost: Free! Just make sure to tip your guide
Hours: Varies by tour. Check the website for more information.
Although a walking tour may not be the most preferable of things to do in Chicago in the winter, Free Tours by Foot offers a Petway System tour. This tour takes visitors through indoor tunnels, paths, and ridges throughout Downtown Chicago. Visitors will see multiple gorgeous lobbies, explore amazing Chicago art and architecture, and some places to eat all while staying inside! Free Tours by Foot also offers several other tours as well.
Where to Eat in Chicago in the Winter
Chicago style pizza is a must on any Chicago trip. There are a TON of places that offer Chicago style pizza and argue they are the best. The following are a few of my favorites to grab some deep dish pizza.
Flora Fauna
Cost: $$
Hours: Mon-Thurs: 4-11pm, Fri: 4pm-12am, Sat: 10:30am-3pm, 4pm-12am, Sun: 10:30am-3pm, 4-11pm
Flora Fauna is the perfect place for brunch. They offer a variety of unique dishes. We opted to try the avocado toast, the sweet potato waffle fry nachos, and the bread pudding French toast. The sweet potato waffle fry nachos were my favorite! You can also buy a bottle of champagne for the table and they will bring out a variety of juices to make mimosas. Another unique option is visitors can choose a base cocktail (like a margarita) and then they have different flavors you can add to it. I opted to get the base as a gin and tonic and added the strawberry aloe mix to it. It was so delicious and definitely unlike any drink, I have had before.
Gino’s East
Cost: $$
Hours: Varies by location
Gino’s East opened in 1966. It has a few locations spread throughout Chicago and several in other places in the United States. Gino’s is also willing to ship your pizza anywhere in the United States (for a price)! They have different sized pizzas you can order, so it is a great place for a larger group.
Lou Malnati’s
Cost: $$
Hours: Varies by location
Lou Malnati’s is one of the best known Chicago-style pizza places. It contains 56 locations throughout Chicago. The first location opened in 1971, but Lou had been making pizzas since the 1940s. Lou’s offers a ton of different topping options and is another good place for a large group.
Chicago Pizza and Oven Grinder Company
Cost: $$
Hours: Mon-Thurs 4pm-7pm, Fri: 4pm-12am, Sat: 11:30am-12am, Sun: 11:30am-11pm
Over Grinder is another fantastic option for pizza and this one is very unique. They are known for their pizza pot pies and Mediterranian Bread. You can choose the type of sauce (marinara or meat), and if you want mushrooms. If you order a salad or an appetizer, one half pound pot pie is plenty for two people.
Portillo’s
Cost: $-$$
Hours: Varies by location
Portillo’s serves a variety of Italian fare but is known for their Chicago-style hot dogs, and Italian beef sandwiches. They also serve other sandwiches, burgers, pasta, salads, and delicious milkshakes. This restaurant is a counter order restaurant, so the service is quite quick! There are several locations around Chicago and other places in the United States.
Warm-up at a bar: The best bars to visit in Chicago in the Winter
One way to warm up quickly on a cold day in Chicago is to visit the local bars. Chicago has endless bars, but some of them are quite unique and they are the perfect things to do when visiting Chicago in the winter.
I/O Rooftop Lounge at The Godfrey
Cost: $
Hours: Mon-Fri: 2pm-2am, Sat: 11am-3am, Sun: 11am-2am
This rooftop bar is a must when visiting Chicago. During the winter season, The Godfrey rooftop has heated igloos on their outdoor patio. In order to go in these, you must have a reservation ahead of time. There is also a large indoor space with lots of standing room. Make sure to brave the cold on the outdoor patio for a little bit to check out the nice views of Downtown Chicago.
Green Door Tavern/The Drifter
Cost: $
Hours: Tues: 5pm-12am, Wed-Fri: 5pm-2am, Sat: 5pm-3am, Closed Sunday and Monday
The Green Door Tavern is a traditional pub. They serve a variety of appetizers and have a full bar. What makes them unique is the speakeasy inside the tavern! Head towards the bathrooms, and look around to find The Drifter Speakeasy. It does not cost to get in unless there is a show going on. Then there will be a $6 cover charge. When we visited, there was a burlesque show. Inside, their drink menu is on Tarot Cards and they have some unique drinks that change. They also have the option for a surprise drink where you can pull a fortune cookie out of a Buddha cookie jar. However, beware: you may end up with a shot and not a drink!
The Signature Lounge
Cost: $$
Hours: Sun-Thurs: 11am-12:30am, Fri-Sat: 11am-1:30am
The Signature Lounge offers the same views as the 360 Chicago, but for a cheaper price. It is on the 95th floor of the John Hancock Building. Grab a drink and admire the amazing views from above while resting your feet. I recommend getting there early on the weekends as the line can get quite long. During the weekdays from 4-7pm, they offer a $10 happy hour with some drinks and light bites to eat.
Three Dots and a Dash
Cost: $$
Hours: Sun-Fri: 4pm-2am, Sat: 2pm-3am
This tiki bar offers a plethora of tropical drinks. Visitors can almost imagine they are sipping away on a cocktail on a warm tropical beach. This bar is hidden down an alleyway. Look for the tiki torches lining the entrance. I recommend making reservations to ensure you can get inside. It gets quite popular on the weekends.
Have I convinced you to brave the cold and travel to Chicago during the wintertime? There are so many fun things to do in Chicago during the winter, so do not pass up on the opportunity if given the chance. It is the perfect destination for a budget-conscious traveling teacher!
We visited Chicago in November once and there was a good amount of things to do there! Our favorites were the field museum and the aquarium.
November would be a good time to go! The field museum is one of my favs too.
Chicago looks like so much fun — even in the winter chill! I love the Bean — it’s just so fascinating. My favorite activity on my last visit was the architectural boat tour. I learned so much about the city.
It is a fun city to explore. I want to take one of those boat tours next time.
This is such a great post for Chicago during the wintertime! The closest to winter I’ve been in Chicago was in March but even then the wind chill was crazy cold! Saving this post to reference hopefully I’ll be back soon one day 🙂
Chicago must have been having a cold winter that year!
Chicago looks like an amazing destination! I always read about the cold during the winter, but this post got me excited to visit Chicago during those cold months and cozy up in the cafes with some amazing food. That food picture made me hungry!
Exactly! I don’t mind the cold at all especially when there is so much inside stuff to do.
I only live a few hours from Chicago and have been planning to take a trip there soon. It’s nice to have an entire list of indoor activities that don’t involve being outside for long periods of time. Especially since it can get so cold!
The Chicago nightlife scene is off the hook! So cool that you made it out to all the cool places. My favourite hands down is the Green Door Tavern. Good all year long, but especially fun to hide in during the winter.
It was so awesome! There are so many cool bars to go to especially in wintertime.
Yah! Also good for summer time when it’s so humid.
I’ve been to that Molly’s cupcakes with the swing for chairs! How fun, loved reading this 🙂
It was a cute place!
I’ve heard so many great things about Chicago and I’d love to visit one day… especially to check out Goose Island Brewery!
Goose Island was awesome!
I’d love to visit the Chicago Architecture Center and have brunch at Flora Fauna!
The Architecture Center was awesome and the brunch at Flora Fauna was so delicious!
That pizza looks amazing! Thanks for all the great tips 🙂
It was so good!
Love your recommendations. It’s so cold outside and these look great!
So many things to do! I know the winters are cold. I am sure the views from the Willis tower would be incredible, especially with some snow on the ground.
I grew up not far from Chicago and LOVE this city! Winters can be brutal, but this is a great list of things to do without getting *too* cold!