Don’t shy away from the Midwest during wintertime! While it might be cold, there are plenty of things to do in Chicago to keep you warm, or to get into the festive spirit. Read on to discover why you should visit Chicago in Winter.
This is a guest post written by Valentina from Valentina’s Destinations
Why Visit Chicago in Winter?
Chicago is one of the largest cities in America. It’s easily accessible through O’Hare International Airport, or by Amtrak train lines. The city sits on the edge of Lake Michigan and is cut in half by the Chicago River. It’s well connected by public transportation, especially subway and bus routes.
Chicago is an international hub of culture and commerce. You can choose to visit many world-class museums, award-winning restaurants or seemingly endless entertainment options. You’ll find shopping for everyone, from affordable outlets to luxury boutiques. There are also numerous skyline photography opportunities for cityscape lovers.
Winter Weather in Chicago
Despite the abundance of exciting things to do in Chicago, many travelers avoid visiting the city during wintertime because of the cold. Winter in America’s midwest is notoriously windy, snowy, and freezing!
If you are planning to visit Chicago in the winter, try to visit in December. Earlier in December, you expect daytime highs in the 40s and 50s℉ with night-time temperatures dipping into the 30s℉. Later in the month, you’ll likely find daytime highs in the 30s – 40s℉ with nighttime dips into the 20s℉.
There isn’t typically as much snowfall in December. About half the days will be sunny, and the other half cloudy. With milder winter weather and an assortment of fun and festive activities, December is the best winter month to visit Chicago! Be sure to dress appropriately.
READ MORE: The Best Free Things to do in Chicago
The Best Things to do in Chicago
Chicago is a four season destination, so I’d be remiss if I didn’t mention some of the top things to do in Chicago at any time of year:
You can browse more activities and tours in Chicago here or enjoy some of the best free things to do in Chicago. While you’re visiting Chicago in the winter plan to visit Olympic National Park, as well!
Awesome Things to do in Chicago in December
Zoo Lights
The Lincoln Park Zoo is one of Chicago’s top-rated tourist attractions. It’s famously the only privately managed free zoo in America and has been a part of Chicago’s history since 1868!
Every season of the year, there are new ways to enjoy this community staple. During the summer, you can attend food festivals and concerts at Lincoln Park Zoo. In Autumn, there are fun ghost tours offered on the property.
However, no season is more famous than winter as during the month of December, the Lincoln Park Zoo is transformed into a festive spectacle of lights.
Partnering with ComEd and Invesco QQQ, the zoo displays hundreds of twinkling LED lights, an 18-foot Christmas tree, ice sculptures, and much more! Kids will particularly enjoy the light maze, enchanted forest, and Lionel Train Adventure.
Christkindlmarket
The Christkindlmarket has been a Chicago tradition for over 20 years! The flagship location is in the Chicago Loop, at Daley Plaza, although in recent years they also added a Wrigleyville site.
Christkindlmarket is a popular destination among locals and tourists during December and follows the style of a traditional German Christmas market, featuring open-air stalls selling commercial trinkets, food and drinks. It’s a lovely place to shop for unique or handmade items of high quality. While pricey, you can discover items that you won’t find anywhere else. There are particularly wonderful glass ornaments.
Be sure to come hungry to Christkindlmarket! You’ll be able to fill up on schnitzel, potato pancakes, and bratwurst. There are also sweet pastries and spiced wine to keep you toasty warm on a cold winter day.
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Jack Frost Winter Village
The Jack Frost Winter Village is a seasonal pop-up located just west of Chicago’s Old Town neighborhood. During December, 2-acres of land get transformed into a festive Christmas themed attraction.
Visiting the Jack Frost Winter Village is a fun activity for all ages. There is a multitude of larger-than-life displays that make an idyllic backdrop for any holiday card. For example, you can sit on Santa’s sleigh or snap a photo next to a giant Frosty the Snowman.
There are plenty of twinkling lights at the Jack Frost Winter Village. Plus, there’s a Christmas tree farm and plenty of games for the whole family. There are also holiday-themed drinks and snacks to enjoy.
Curling
If you’ve ever tuned into the Winter Olympic Games, you’ve likely heard about or seen the sport of curling in action. During curling, stones are slid along a sheet of ice towards a target. Picture a shuffleboard-like setup.
In curling, there are two teams. Each team has 8 stones (which are heavy, polished rocks). The goal of the game is to score the most points by having the most stones in high-point positions. When a stone is being slid towards the target, your teammates may sweep the ice in front of the stone to direct its path. (Hence, ‘curl.’)
There are two well-known places in Chicago which you can experience curling during the wintertime: the Kaiser Tiger in West Loop and Upstairs at the Gwen in River North.
You Should Also Read: Things to do in Colorado Springs in Winter
Ice Skating in Chicago
Ice Skating is another one of the popular wintertime activities to enjoy in Chicago. There are a few excellent places to enjoy ice skating. If you bring your own skates, ice skating is free! The only cost at Chicago ice rinks is the skate rental.
The most touristy place to go ice skating is in Chicago’s Millennium Park. This is a popular spot, and you’ll see long lines of eager people waiting for their opportunity to rent skates. The other benefit of bringing your own skates is that you don’t have to wait in line!
Navy Pier is one of the top attractions in Chicago. Located in Chicago’s Streeterville neighborhood, Navy Pier is a community hub featuring restaurants, shops, family activities, and event spaces.
During December, Navy Pier’s Pier turns into Winter Wonderfest. It’s the biggest indoor playground in downtown Chicago and is one of the best things to do in Chicago with kids. Indoor activities include the Arctic Express Train, Candy Cane Lighthouse, and visits with Santa.
There’s also an ice skating rink and a giant Christmas tree.
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Find the Holiday Train
Locals and tourists, alike, should be on the lookout for Chicago’s Holiday train! It is one of the most loved traditions of the Chicago Transit Authority or CTA. The Holiday Train tradition was started as a means of spreading holiday cheer, as well as increasing charitable donations.
You can’t miss the Holiday Train because it’s decked out in festive lights and decorations. You’ll also notice that Santa drives the holiday train, and he makes sure to wave to onlookers. If you want to be sure not to miss the holiday train, you can find a complete schedule on the CTA website.
Christmas Around the World
When visiting Chicago during December, be sure to stop by the Museum of Science and Industry. Each year they put out a very special holiday-themed exhibit called, ‘Christmas Around the World and Holidays of Light.’
There are fabulous tree displays and unique global traditions to learn about. Featuring items and information pertaining to the Lunar New Year, Diwali, Ramadan, St. Lucia Day, and Hanukkah. You’ll also find festive holiday outfits from countries like Kenya, Ecuador, Japan and Norway.
The centerpiece of the exhibit is a 45-foot tall Christmas tree that’s decked out in over 30,000 lights! There’s plenty of photo ops here, as well as a holiday-themed gift shop. This exhibit has been a tradition of the Museum of Science and Industry since 1942.
Run the Santa Hustle
If you love to run then the Santa Hustle is the perfect seasonal race for you to enjoy in Chicago. The Santa Hustle is a 5k, so you certainly don’t need to be a professional athlete to participate. This race takes place every December at Soldier Field.
Participants are always rewarded with cool apparel and fun gifts, so sign up on the Santa Hustle website to take part.
Getting There
- Use Skyscanner to find cheap flights to your destination.
- Public buses are the cheapest ways to get to your accommodation from the airport, but a shared shuttle transfer is quicker and cheaper than a taxi - you can pre-book those on GetYourGuide or Viator
- Try Omio for booking trains and Busbud for buses including Greyhound and Flixbus.
Where to Stay
- For hotels, I use Booking.com to check reviews and find the best deals on hotels and apartments wherever I'm travelling to. Hotels.com is another good site.
- If you're on a tight budget, use Hostelworld to find the best hostels all over the world
Hire a Car
- Get a quote for car hire with Discover Cars who compare car rental deals from many companies so that you can choose which is best for your trip.
Book Tours and Activities
- I use GetYourGuide or Viator to book everything from skip-the-line entry tickets to food tours as I can compare options from several companies and choose the best one for me
- If you're staying in a hostel, check out their tours and activities which are usually free or very cheap - and a great way to meet people!
Get Travel Insurance
- Unfortunately, things can and do go wrong when you travel. I never leave home without travel insurance, so consider getting insurance for your trip to cover things like adventure sports and activities as well as emergency medical, lost luggage, stolen items, trip cancellation and more.
- Get a quote for your trip from True Traveller if you're based in the UK, or World Nomads or SafetyWing which both offer travel insurance for backpackers and long-term travellers. Alternatively, use a comparison site like Travel Insurance Master to find the best cover for you.
Check Your Travel Documents
- Don't forget to check the validity of your passport and any other documents for your trip. Use iVisa to check if you need a visa to visit your destination, and get up to date official travel advice from your government, for example on the Department of State website in the US or the UK government website.
Get Cheap Currency
- When travelling abroad, using a travel bank account like Wise means you get great deals on foreign currency - including a fee-free transfer of up to £500 when you use this link to sign up.
Top Money Saving Tip for Backpackers
- Work exchanges are a great way to travel for longer and extend your trip as you can save a ton of money on accommodation. Get an extra $10 discount on Worldpackers here or learn more about work exchanges.
Where to Stay in Chicago This Winter
After exploring Chicago in the winter, you’ll need somewhere to warm up and get a good night’s sleep. Take a look at these hostels and hotels in Chicago:
HI Chicago, The J.Ira & Nicki Harris Family Hostel: This historic hostel offers comfortable and contemporary accommodations in the thriving university district, one block away from Grant Park and the lakefront. >>>CHECK PRICES
Hampton Inn Majestic Chicago Theatre District: Located in the Theater District in downtown Chicago, close to the most popular sights, including Millennium Park and the Skydeck at Willis Tower. Free breakfast makes this hotel a deal in the heart of the city. >>>CHECK PRICES
Hotel Chicago Downtown: This Autograph Collection hotel located in downtown Chicago offers proximity to all the sights and entertainment, like the House of Blues, plus a large work desk and other amenities for digital nomads. >>>CHECK PRICES
If you’d like more options, you can browse hostels in Chicago on Hostelworld, or find great value hotels on Booking. There are also various options for Airbnbs in Chicago too, take a look at some of the rental homes available here.
About the Author
Valentina has always loved planning her vacations. She knows that many people don’t have the time and energy to make meticulous itineraries, but they still want to get the most out of their travels. Valentina’s Destinations allows her to help other busy professionals maximize their experiences. Valentina is originally from Serbia, but she grew up in Chicago. She loves hunting down local restaurants, unique experiences, and hidden gems. You can also find her on Instagram and Facebook.
