20 Things To Do In Chicago In Winter

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Chicago is a fascinating city with plenty to see and do, but the winter months are very cold. The average temperature is -1.1C (30F) and this can last from November until March. It can often snow, and O’Hare Airport estimates that there are 28 ½ days of snow every winter. So, what can you do if you decide to visit during the winter months? Although you can go to museums and other indoor attractions, Chicago also offers exciting outdoor activities, such as ice skating, sledging, light shows and Christmas markets.

If you are going to spend time outside, it’s best to dress in layers, as they keep you warmer than just one thick jumper. It also means that if you go from a cold to a warm environment, you can take off a couple of layers. When you are outside, put on a hat, as heat escapes through your head. Extremities also should be covered, as hands and feet get cold quickly. Thick gloves and socks are the order of the day. Without further ado, let’s look at things you can do in Chicago in the winter. I have chosen both indoor and outdoor activities that I hope you enjoy.

Winter in Chicago

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20 Things To Do In Chicago In Winter

1- Go Ice Skating At One Of The Iconic Ice Rinks

Cropped Shot Of A Young Woman Skating On An Ice Rink
Go Ice Skating at One of the Iconic Ice Rinks winter activities in Chicago.

Ice skating is popular in Chicago, and several ice rinks are set up during the winter months.

One of the most iconic is in Millenium Park, which offers spectacular views of downtown Chicago, busy Michigan Avenue, and the Bean, one of the world’s largest outdoor sculptures.

The Skating Ribbon in Maggie Daley Park winds through pine trees and passes a rock-climbing wall.

It is twice the length of a standard ice-skating rink.

The Midway Plaisance Ice Rink in Hyde Park has a warming centre, so you can nip in and warm up when you get too cold.

The Sky Rink at the Peninsula Chicago Hotel shouldn’t be missed.

It’s the city’s only ice rink in a hotel, and it is perched on the rooftop, so you get spectacular views of Chicago.

The skating rinks rent out skates, and they are usually open from November until early March.

2- Enjoy A Glass Of Gluhwein At A Christkindlmarket

Christmas Mulled Wine
Drinking gluhwein is one of the things to do in Chicago during winter.

Christmas markets are popular all over the world, and the Christkindlmarket in Chicago won’t disappoint.

It opens the week before Thanksgiving and closes in the first week of January.

The market replicates a traditional German Christmas market, with traditional foods and drinks on sale, such as pretzels, bratwurst and other sausages, currywurst, sauerkraut, potato pancakes, gingerbread, stollen, and gluhwein, the German version of mulled wine.

You can even buy a Gluhwein tankard to take home with you.

You can shop here to your heart’s content.

You will find toys, Christmas ornaments and decorations, and all sorts of holiday gifts, such as jewellery and candles.

The market is outdoors, so remember to wrap up warmly.

3- Check Out A Lightshow

Chicago is famous for its light shows which are set up in November for the lead-up to Christmas.

You should see at least one if you are here at this time of year as they are spectacular.

The Magnificent Mile Lights Festival is one of the best, as it has over one million lights.

You will forget about the cold when you see the magical display.

Lightscape at the Chicago Botanical Gardens is another light show that should be on your list.

The pathway is 2 km (1.25 miles) long, and along it, you will see many displays, such as a fire garden and a 33.5-metre (110-foot) tunnel with 100,000 dazzling lights.

If you have children, they will love the Sparkle Light Festival at Rosemont’s Impact Field, especially as there are train rides and snow tubing as well as the lights.

There are five illuminated villages to explore and a maze to try to get out of.

4- Visit A Museum

Field Museum In Chicago
The Field Museum in Chicago in the winter.

Now, to something you can do to escape from the cold weather.

Chicago has many museums to choose from, and it can be difficult to know where to start. I have chosen a few that I think you might like.

If you are interested in art, the Art Institute of Chicago houses more than a quarter of a million pieces of artwork dating back as far as 5,000 years.

It is interesting to see how art has changed over the centuries, and you could easily spend half a day here.

The Field Museum of Natural History has millions of artefacts dating back thousands of years, showcasing history, art, archaeology, and science.

It houses the largest T-Rex skeleton found in the world.

The Adler Planetarium Museum shouldn’t be missed.

It is the oldest planetarium in the US and has three theatres where you can watch fascinating shows about the night sky.

It is another museum where you can spend plenty of time, as it also has a large collection of historical artefacts that go back as far as Mediaeval Europe.

  • The Art Institute of Chicago is at 111 S. Michigan Avenue, Chicago 60603
  • The Field Museum of Natural History is at Near South Side, Chicago 60605
  • The Adler Planetarium Museum is at 1300 S.Lake Shore Dr., Chicago 60605

5- Have a Drink In A Snow Globe at the Godfrey Hotel

Urban Skyline Of Chicago Loop And Frozen Lake Michigan
The Urban Skyline of Chicago reveals glimmers of what to do in Chicago in winter.

The Godfrey Hotel has a rooftop bar with spectacular views of the Chicago skyline.

In the winter, it’s too cold to sit outside, so the hotel turns the space into a winter wonderland by erecting igloos.

The smaller igloos can fit up to six people, and the large igloos can seat up to ten.

They are heated, so you will keep warm while you sip your drinks and admire the lights on the rooftop.

You have to make a reservation to secure an igloo, and the smaller igloos can be reserved for up to an hour and a half, while the bigger ones can be booked for up to two and a half hours.

The Godfrey Hotel is at 127 W. Huron Street, Chicago 60654

6- Go And See The Millenium Christmas Tree

Christmas Tree In Chicago
Gazing at the Christmas tree is a popular “what to do” in Chicago in the winter.

The Millennium Christmas Tree is a spectacular evergreen tree and is always at least 16.7 metres (55 feet) tall.

It is worth going to see it at dusk, but if you are lucky enough to be in Chicago the week before Thanksgiving, you should go to the lighting ceremony.

The lighting ceremony takes place on the Friday before Thanksgiving and, like all the holiday events in the park, is free to attend.

There is a show before and after the lighting of the tree, and fireworks coincide with the lights being switched on.

It can get crowded, but there are screens throughout the park showing the whole ceremony.

The tree is taken down on January 7th every year, and a new one is erected the following November.

Recommended tours:

7- Catch Santa’s Holiday Train

Bridge Over Chicago Train
Catching Santa’s Holiday Train is one of the fun events in Chicago in winter.

Each holiday season, the Chicago Transit Authority decorates one of its trains with lights and other festive decorations.

Santa sits in an open-air flatcar and waves to passengers at each station while elves sing to the passengers.

If anything can put you in the Christmas mood, this will.

You can have photos taken with Santa at designated times, which you can find online.

It will also tell you where the train will stop and at what time.

There is also a holiday bus in Chicago that is festively decorated and has a Santa waving from the roof hatch.

It goes on different routes, so look them up online.

8- Enjoy Curling And A Cocktail At The Gwen

This five-story hotel has an iceless curling rink on the rooftop during the winter months, where you can enjoy a game of curling with a signature cocktail.

Fire pits are set up so you will be kept warm, and food is also served.

A curling rink is also set up in the winter in the beer gardens of the Kaiser Tiger.

It has infrared heaters to keep you warm and serves a potent hot chocolate.

  • The Gwen is at 521 N. Rush St., Chicago 60611
  • Kaiser Tiger is at 1415 W. Randolph St., Chicago 60607

9- Visit An Indoor Garden

If you are looking for an indoor activity, visit one of the indoor gardens in the city, where, apart from being warm, the great thing is that admission is free.

The Lincoln Park Conservatory has several rooms dedicated to exotic plants, including the Victorian Palm House, the Fern Room, the Orchid House, and the Show House.

The Show House hosts flower shows throughout the year.

Garfield Park Conservatory covers 0.8 hectares (2 acres) and is a massive greenhouse, where you will find the Palm House, the Fern Room, the Desert House and the Aroid House.

It also houses waterfalls and koi ponds, and you may see turtles and birds.

  • The Lincoln Park Conservatory is at 2391 N. Stockton Dr,. Chicago 60614
  • Garfield Park is at 100 N. Central Park Avenue, Chicago 60624

10- Go Sledging At Soldier Field

Sledging is one of the most fun things you can do in the snow, and this goes for adults as well as children.

Soldier Field, home of the Chicago Bears, is the perfect place to go sledging in Chicago.

It has a slope that is longer than 61 metres (200 feet). When you get to the top, make sure you have a good look around before getting on your sledge.

The view of Lake Michigan is spectacular.

Another activity in the snow is snowshoeing, and you can do this east of Soldier Field on Northerly Island.

It has a nature trail with lake and city skyline views, and there are Polar Adventure Days where you can meet animals such as Siberian huskies and wolves, as well as birds of prey.

11- Catch A Comedy Show

Many famous comics have started their careers in Chicago, and there are plenty of comedy clubs and theatres where you might catch rising stars.

One of the most famous comedy clubs is The Second City, where stars such as Bill Murray and John Belushi began their careers.

It has several stages, and the shows are based on improvisation and interaction with the audience.

The themes used are usually political or social satire.

iO Theatre also concentrates on improvisation, but in long form rather than short, and they can deal with any type of subject.

The theatre also hosts stand-up comics.

Laugh Factory is open every night of the week and hosts an impressive list of local stand-up comedians.

At times, they have the biggest names in the industry performing. Check their website to see who’s on.

12- Head To The Top Of The Willis Tower

Willis Tower Reaching For The Sky
Seeing the view fromWillis Tower is one of the fun things to do in Chicago in the winter.

The Willis Tower, at 442.3 metres (1451 feet) high, is the third-tallest building in the Western Hemisphere.

On the 103rd floor, you will find Skydeck Chicago, an observation deck with an added thrill. Skip the line and book your tickets here.

You might find that just looking down from the 103rd floor is scary enough, but it’s nothing compared to going out onto the Ledge.

The Ledge is a series of glass-panelled boxes that protrude out of the building, giving you a view right down to the street from the bottom of the box.

They extend 1.3 metres (4.3 feet) out of the building and are 412.4 metres (135.3 feet) above the ground.

You will have a magnificent view – that is, if you have the nerve to open your eyes!

The Willis Tower is at 233 S. Wacker Dr., Chicago 60606.

13- Go To Zoolights At Lincoln Park Zoo

This is another light festival, but it deserves a mention of its own as it’s set in Lincoln Park Zoo, so you also have the opportunity to see the animals after hours.

The light festival starts in the middle of November and finishes on January 7th.

The zoo is lit up with over two million lights and is a real winter wonderland.

Strands of lights drape the trees, turning the zoo into a magical forest.

There is a 5.48-metre (18-foot) Christmas tree, which you should take a photo of.

Your kids can also have their photos taken with Santa.

3D glasses are available in the zoo shop, so you can see the lights in a completely different way.

What you will see are five-pointed lights, and the result is another magical experience.

Lincoln Park Zoo is at 2001 N. Clark St., Chicago 60614. Explore on a scavenger hunt.

14- Shop ‘Til You Drop Along The Magnificent Mile

The Magnificent Mile covers 13 blocks along North Michigan Avenue.

Here you’ll find over 460 shops covering both high-end designer stores such as Cartier and everyday brands like Gap.

This is a time to wear layers, as you will continually be going from the cold air into hot buildings.

You will find three shopping malls along the Magnificent Mile, including Water Tower Place, where you will find most of the department stores.

Luxury shops are to be found at The Shops at North Bridge, and a six-story Bloomingdales is at 900 North Michigan Shops.

You can easily spend all day along the Magnificent Mile, especially as there are 275 restaurants for you to choose from for lunch.

You’ll find a wide range of cuisines on offer, such as Italian, Mexican, French, Indian, Asian, and, of course, American.

15- Head To A Jazz Or Blues Bar

It’s not only New Orleans that has a legendary jazz scene.

Chicago also has a long history of jazz music, and you can find many clubs where you can spend a few hours listening to jazz and sipping cocktails.

The most iconic jazz club is The Green Mill, which has been around for over 100 years, operating as a speakeasy during prohibition.

It was even a favourite haunt of the gangster, Al Capone. Now, it has live jazz on every night and stays open until the early hours.

Andy’s Jazz Club is another great venue.

Here, you can listen to live music, sip a cocktail, and indulge in Cajun-inspired dishes.

Enjoy brunch at the weekends when admission is free.

Blues is also popular in Chicago.

Blue Chicago is an intimate club which honours some of the best blues musicians in the city, while Rosa’s Lounge combines local musicians with up-and-coming national acts.

  • The Green Mill is at 4802 N. Broadway St., Chicago 60640
  • Andy’s Jazz Club is at 11 E. Hubbard St., Chicago 60611
  • Blue Chicago is at 536 N. Clark St., Chicago 60654
  • Rosa’s Lounge is at 3420 W.Armitage Ave., Chicago 60647

16- Take A Ride On The Centennial Wheel

The Centennial Wheel is one of the many attractions on Navy Pier.

However, it is one of the few rides that stays open all year.

This is because the 42 gondolas are enclosed and climate-controlled, so they are cool in the summer and warm in the winter.

You may have to wait in line to get on so make sure that you are well wrapped up.

At the top of the wheel, you are 61 metres (200 feet) high, and unsurprisingly, you will have a brilliant view of Lake Michigan and the city.

Don’t worry about the wind.

Yes, Chicago is known as the windy city, but the Centennial Wheel is built to withstand even typhoons.

17- Visit The Chicago Architecture Centre

Chicago has a reputation for interesting and innovative architecture.

If you want to learn more about this, head to the Chicago Architecture Centre.

It hosts both permanent and temporary exhibits covering such topics as Chicago neighbourhoods, landscape architecture, and individual architects who have left their mark on the city.

The highlight is the Chicago City Model Experience, which has over 4,200 model buildings.

The centre also offers tours led by expert docents who will tell you about the stories behind the construction of homes, hotels, parks and even cemeteries.

The Chicago Architecture Centre is at 111 E. Wacker Drive, Chicago 60601.

Recommended tour: Chicago Architecture Walking Tour: The Underground Pedway & Secrets of the Loop

18- Try The Chicago Deep Dish Pizza

Double Crust Large Speciality Chicago Pizza
Chicago Pizza things to do in Chicago in the winter.

Deep-dish pizza is different from regular pizza.

It is cooked in a pan on the hob rather than in the oven and gets slightly fried due to the oil in the pan.

It has a tall crust, though not necessarily thick, of around 5 cm – 7.5 cm (2 ins – 3 ins) high.

Into this is first piled lots of cheese, then meat or vegetables, and finally a sauce. It is more like a pie rather than a flatbread.

Deep-dish pizza was invented in Chicago in 1943, supposedly at Pizzeria Uno, and it can be tried all over the city.

Lou Malnati’s has a great reputation, as does Giordano’s.


19- Visit The Jack Frost Pop-Up At Fulton Market

This pop-up is set up for the holiday season in Fulton Market and is well worth a visit if you are in Chicago between mid-November and early January.

It covers 0.8 hectares (2 acres) and offers hours of fun for the whole family.

There is an ice-skating rink and winter bumper cars, which the kids will enjoy.

When it gets dark, you can take a stroll through the beautiful Christmas tree walk, which has a total of one million lights.

There are shops selling everything Christmassy, and there are photo opportunities to be had.

Adults can get into the festive spirit with a hot chocolate with a little boozy addition.

The Jack Frost Christmas Pop-Up is at 170 N. Green St., Chicago 60607

20- Grab A Drink at Frosty’s Christmas Bar

If you love Christmas and are grown up, you may not want to admit that the season is magic.

If this sounds like you, head to Frosty’s, where you can have a drink or two in an adult Christmassy atmosphere where everybody embraces the Christmas season.

Frosty’s pops up in the middle of December for six weeks and has four bars on three floors as well as two dance floors.

You can enjoy your cocktails or beer among elaborate decorations, such as life-size toy soldiers, Santas, and elves.

You will be served by servers dressed up either as Santa or his helpers, and there is a good range of seasonal cocktails on offer.

The great thing is that everybody who comes here loves Christmas as you do. Entry is 21 and over.

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cropped irena nieslony.jpg
Irena Nieslony was born in Windsor, England but now lives on the island of Crete, Greece, in a small village called Modi near the city of Chania. She has visited 32 countries in Europe, North and South America, Asia, and Africa. Her favourite country is Tanzania as she loves wildlife and was lucky enough to see ‘The Big Five”. She also loves Egypt, as ancient history intrigues her, the southern states of the US and the cities of Memphis, Nashville, and New Orleans for music. She has a B.A. Honours degree in English and Drama from Westfield College, University of London. She has been writing for over 13 years and has 13 novels, 7 short stories and thousands of articles published.