Chicago / Illinois / North America / Traveling / United States

5 Reasons NOT to Avoid Chicago Winters


The bitter Chicago cold and wind from the lakefront can be intimidating. Growing up in the Chicago area, I know how brutal those winds can be. Chicago winters can be so cold that many people completely avoid visiting this beautiful city during the winter months. While I do enjoy Chicago’s wonderful summers, today I’m giving you 5 reasons to brave the Chicago winter weather instead of running away to the Bahamas.

1. Ice Skating

The brand new Maggie Daley Park just opened, which is now home to a fun ice skating ribbon with the Chicago skyline in the backdrop. I will warn that it can get very crowded here, so come prepared! Having your own skates is ideal, so if at all possible try and snag a pair from a used sporting goods store. It’s free to skate, but it costs $12 to rent skates plus up to an hour and a half’s worth of your time waiting in line for rentals… probably longer than you will actually skate. Not a skater? You get some beautiful views of the sunset from the Maggie Daley Park and it’s always fun to people watch with the crowds of people skating on the ice!

Chicago Maggie Daley Ice Skating Ribbon

Another option for an outdoor Chicago ice skating rink with beautiful views of the city is Millennium Park. You’ll likely still have quite the wait here for rentals, so your best bet for each of these rinks if you don’t have your own skates is to arrive early to try and beat most of the rush. Either way, you’ll be able to enjoy stunning views while gliding along the fresh outdoor ice.

Chicago Cloud Gate Bean

You can always see the famous bean year round!

2. Holiday Lights and Decorations

The Chicago winters may be cold, but the holiday lights and decorations will warm you up as they transform the city into a magical place during the winter. The decorations throughout the city and the way the parks and streets light up with the holiday spirit every winter is sure to get you in the mood for winter festivities!

Marshall Field and Company Chicago

3. Marshall Field’s Macy’s on State Street

Every year since the early 1980s, the large display windows around the outside of the Marshall Field and Company building on State Street were decorated in detail by a talented team of artists, carpenters, painters, engineers, costume designers, and more. As the inventors of the department store, window displays took on a new twist around Christmas-time that told a new story every year. In 2006, Macy’s took over when they bought out Marshall Field’s, but they still continued this holiday tradition and renamed it “Macy’s on State Street”. This year’s theme for 2014 is “The Journey of a Christmas Wish” and follows a young girl’s wish list as she travels to Macy’s. The stories weaved together by each window along State Street never fail to transport visitors to a dreamy winter wonderland!

Macys on State Street Christmas WindowsTo top off your stay, you can also visit the Walnut Room on the 4th floor which remains a holiday tradition for many Chicagoans. This iconic destination opened in 1907, when Mrs. Hering, an employee of Marshall Field’s who worked in the women’s hats department, brought homemade pot pies in to work so her clients would not be hungry while they were shopping. You can still enjoy a traditional pot pie today made with Mrs. Hering’s original recipe, and feel free to enjoy all 9 floors of the store while you’re there! If you visit from November through early January, you will be able to enjoy your meal in the presence of the famous 45-foot Grace Tree.

4. Live Performances

There are so many options in Chicago when it comes to entertainment. If you’re really looking to escape from the cold for a few hours, check out what shows are running when you are in the area. If you visit Chicago in December, going to the ballet to see the Nutcracker is a must! You can also take a look at Broadway in Chicago as they always have a variety of musicals and plays running throughout the year. With hundreds of theaters and venues throughout the city, there certainly isn’t a shortage of live performances to attend!

Nutcracker Ballet Chicago

5. Christkindlmarket

Celebrate German culture in Chicago and check out Christkindlmarket, Chicago’s largest open-air market. With common German food, drinks, and items, a variety of entertainment, and plenty of visitors from all over the world, this German inspired tradition is a free must see attraction!

Now that you’ve experienced the best of what Chicago has to offer in the winters, you are free to escape to the tropical destination of your choice. Bearing through the bitter cold, I’d say you’ve earned it!


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  • Instagram 2015 Travel Photo Roundup
    December 30, 2015 at 7:16 am

    […] I rang in the new year in Chicago, and took this just after ice skating at the newly opened Maggie Daley Park. While it’s easy to be deterred by the bitter winters, it can actually be a really magical time of year to be in the city if you bundle up warm enough. Here are 5 reasons not to avoid Chicago winters! […]

  • Brandon @ Green Global Travel
    February 25, 2015 at 8:43 pm

    If you can bear the cold, Chicago is the time of place to go this time of year. That ice skating rink looks like a blast.

    • Marissa Sutera
      February 27, 2015 at 3:06 pm

      It was tons of fun! Although super crowded for sure, so going during the week is a must if possible. Sticking it out through the cold will definitely be worth a winter visit to Chicago!

  • James
    February 2, 2015 at 11:46 am

    After checking out multiple Christkindlmarkts in Nuremberg, Berlin, Potsdam, and a few other German spots a few years back, I’d really like to see how Chicago stocks up. Realistically as long as they’ve got Gluhwein, it’s all good haha.

    • Marissa Sutera
      February 2, 2015 at 3:35 pm

      So true! It’s not quite the same, but it’s worth experiencing if you have the chance to visit Chicago in the winter!

  • Darren
    January 10, 2015 at 2:05 am

    Chicago is on my list of places to visit as I travel across the USA later this year. I’d love to go and watch a baseball game, and explore the city. Great photos.

    • Marissa Sutera
      January 10, 2015 at 5:22 pm

      Thanks Darren! Cubs games are a lot of fun, especially if you explore Wrigleyville afterwards 🙂 Enjoy!

  • Tonya {The Traveling Praters}
    January 5, 2015 at 1:55 pm

    Chicago has been on my list places to visit for years but I’ve never considered a winter visit. I’m not a fan of the cold but the lights and decorations are alluring.

    • Marissa Sutera
      January 5, 2015 at 5:45 pm

      I hope you have the chance to check it out! The cold can be a bit discouraging, but there is so much to explore (both indoors and out) in the winter that it can make for an amazing trip! Thanks for reading Tonya 🙂

  • Jolanta aka Casual Traveler
    January 4, 2015 at 3:47 pm

    I completely understand! Boston may or may not be cold in the wintertime, but that’s not a reason not to visit. Every big city has plenty of things to see and do even in the wintertime, and I see Chicago is no exception. I have actually never been to Chicago. I do hope I’ll end up there some time, be it winter or some other season.

    • Marissa Sutera
      January 5, 2015 at 5:43 pm

      Chicago is great all year round! I used to have that fear of winter, but it can actually be an extra special trip for some cities in the winter 🙂

  • Sarah Ebner
    January 3, 2015 at 12:11 pm

    This is great – I just told a friend who was worried about visiting Chicago in winter that she’d love it, despite the weather – am going to send this onto her! I spent Christmas there many years ago and think it is one of the most wonderful cities I’ve ever been to.

    • Marissa Sutera
      January 3, 2015 at 12:45 pm

      Thanks for sharing Sarah! The cold weather certainly shouldn’t deter anyone from seeing how beautiful Chicago is in the winter. Now with the Maggie Daley park, it just seems to keep getting better! As long as you layer up it can be a really great time! 🙂

  • Sarah | Every Mile a Memory
    January 3, 2015 at 6:57 am

    This post just made me incredibly homesick. I am currently in Thailand and have been travelling throughout the winter, but I am from Northwest Indiana. Christmas in Chicago is actually my favorite season for the city. I love that you still call it Marshall Field’s as well! I’ve been away for a few years now and haven’t yet seen the ice skating rink in Maggie Daley Park. How fun does that look! Are you still in Chicago? If so, you should check out the sledding hills and other winter activities at Indiana Dunes State Park in Chesterton, IN. Just another reason to love winter in the area.

    • Marissa Sutera
      January 3, 2015 at 12:39 pm

      Sending some Chicago love your way Sarah! 🙂 You for sure need to check out the Maggie Daley Park next time you’re in the area, it’s a lot of fun (and the park itself makes me want to be a kid again)! Sadly, I am leaving today but it really hasn’t been the best sledding weather since I’ve been in town. It’s actually raining today! You never know with Chicago weather… I’ll have to save that for next winter!

  • Esther
    January 3, 2015 at 1:54 am

    Aww, this looks really nice! I’ve noticed a fair amount of ‘winter haters’ amongst travel bloggers. They just go to wherever the sun is. I do understand, sun is nice and all that. But I definitely have a thing for winter cities too. I love German cities in winter (the Germans just know how to make it all cosy) and there is something magical about Scandinavia in winter too! Your pics of Chicago look great as well, I’d see no reason to avoid it 🙂

    • Marissa Sutera
      January 3, 2015 at 12:35 pm

      Thanks Esther! I love warm weather, but the magic of winter always gets me 🙂 German cities are great winter destinations as well!

  • Karyn @ Not Done Travelling
    January 2, 2015 at 3:44 pm

    I’m in Melbourne, Australia and it’s 41 degrees here so this post has cooled me off nicely. lol!

    I actually was meant to be spending this Christmas and New Years in New York but had to cancel. Everybody told me that was a good thing because it’s been so cold in your part of the world lately. But it’s always good to look at the positive so I’m glad to see there’s so many great things about Chicago in the winter, even if the temperature is way down. 🙂

    • Marissa Sutera
      January 2, 2015 at 4:09 pm

      It sure has been pretty cold over here lately! I feel like I’ve always been a downer about Chicago weather in the past, and visiting home this year was a turn around for me. I realized how many wonderful things there are to do and see during the winter, you just need to be prepared and bundle up extra warm! Thanks for reading Karyn!


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