Chicago, Destination, USA

Chicago Winter Bucket List

Chicago is the perfect place for an all-ages, especially during the magic of winter. You can catch a bird’s eye view of the city from 360 Chicago or experience it from the magic of The Polar Express. Regardless of your viewpoint, The Windy City has it all. Check out our Chicago winter bucket list for the best-of-the-best this winter in Chicago.

Chicago Winter Bucket List

The Langham, Chicago

The Langham, Chicago

At the top of your Chicago winter bucket list should be The Langham, Chicago. It’s more of an experience than a hotel. From the moment you pull up to the doors at The Langham, you will understand what I mean. You’re greeted by a stylishly dressed host or two as well as valet drivers. They will treat you like royalty and attend to your every need.

While it is remarkable all year round, there are many reasons to put The Langham, Chicago on your Chicago winter bucket list. Sparkling holiday decor, seasonal music, a Christmas tree lighting, visits with Santa, festive holiday meals, and a tasty Holiday Tea all make The Langham the best holiday treat.

Some of the most remarkable experiences at The Langham for your list include:

Holiday Afternoon Tea

Holiday Afternoon Tea at The Langham, Chicago

Celebrate the magic of the season with The Langham Holiday Afternoon Tea. Delicate pastries and savory petite sandwiches are the perfect way to spend an afternoon with those you love.

Warm yourself as you sip Langham’s unique tea blends and sample seasonally-inspired treats.

The only thing more welcoming than the tea is the smiles and kindness from the staff.

The Langham Club

The Langham Club

If visions of sugarplums dance in your head, The Langham Club is the place for your Chicago winter bucket list. It is a private, luxurious haven for guests who prefer a discerning level of comfort.

Located on the uppermost floor of the hotel, this 4,000 square foot lounge features panoramic views of Chicago. A breakfast buffet, all-day refreshments, afternoon tea, premium bar service, and hors d’oeuvres are served daily. Although we did enjoy a number of delicious meals around Chicago, we could have had everything, including meals, snacks, drinks, and treats at The Langham Club.

Additionally, attentive and personalized service is provided by dedicated Club Concierge.

Whenever we returned from an afternoon of exploring the city, our first stop was at The Langham Club to relax and have refreshments.

The Pool and Spa

The Pool and Spa at The Langham, chicago

The hotel is home to Chuan Spa, where guests can indulge in signature wellness and holistic treatments as well as a swimming pool, fitness center, and innovative relaxation facilities.

Royal Sonesta Chicago Downtown

Royal Sonesta Chicago Downtown

While you can’t beat the AAA Five Diamond service and amenities at The Langham, another bucketlist-worthy hotel in the heart of the city is Royal Sonesta Chicago Downtown.

The fully renovated hotel makes the list because of the Family Suites option. Family suites include one bunk bed with two twin beds in the separate lounge area.

Royal Sonesta Chicago Downtown provides some of the largest guest rooms in Chicago. Their sophisticated newly renovated Junior Suites come equipped with a separate lounge/living room area, expanded wet bar, and full refrigerator. The rooms feature a king-size bed with luxurious linens. Stay productive in the spacious work area adjacent to the bed then relax with bath amenities in the soaking tub or separate rainforest shower.

When you’re traveling with children, big rooms with separate sitting areas are worth their weight in gold. No adult wants to go to bed at their toddler’s bedtime. A separate area makes sure everyone sleeps better and gives you the freedom to stay up in the evening.



Soaring 1,000 feet over Chicago’s legendary Michigan Avenue, 360 CHICAGO is one of the city’s most unique attractions. It offers breathtaking views of Chicago’s lakefront, magnificent skyline, and four neighboring states.

Even if you only have two days in Chicago, 360 Chicago should be on the top of your list.

Image the freshly-fallen snow blanketing Chicago as you sip hot chocolate from the on-site Bar94 and stare at the unique architecture and splendor of the city.

If you are looking for the very best way to see Chicago from above, make sure your first stop is 360 CHICAGO.

Christkindlemarket Chicago

Christkindlmarket combines cherished German tradition with local charm. Inspired by the 16th century Christkindlesmarkt in Nuremberg, Germany, one of the first outdoor markets of its kind, the Christkindlmarket is well-known for its vendors’ high quality gifts and food, holiday cheer, and for being the ideal place for families to make unique memories.

The smell of roasted nuts, fresh pretzels, bratwurst, and hot spiced wine, the sound of festive music, and the glimmer of sparkling Christmas ornaments, all in a cozy atmosphere – a visit to the market takes all your senses on a journey!

If you’re looking for a special keepsake from your trip to Chicago, this is the best place to find it.

Shedd Aquarium

Shedd Aquarium, Chicago

From whales to snails, you’ll meet 32,500 aquatic creatures from around the world at Shedd Aquarium. Although you can visit Shedd Aquarium anytime, it’s worth adding to your list whenever you go.

Kids and their families come face to face with beluga whales, dolphins, sea otters, sea lions, and penguins.

At Polar Play Zone, kids and their families can play, pretend, and discover through hands-on activities.

Then meet some of Shedd’s critters up close during live animal encounters in the Waters of the World galleries, talk to a diver in the 90,000-gallon Caribbean Reef, take a walk through a flooded forest in Amazon Rising and watch sharks overhead in Wild Reef.

Shedd Aquarium is a joy for the entire family.

Navy Pier’s Light Up the Lake

Navy Pier’s Light Up the Lake

Light Up the Lake is an indoor, temperature-controlled holiday experience. It offers more than 600,000 twinkling lights, a regulation-size Alpine ice rink, authentic holiday beer garden, kiddie train rides, Santa’s Village and gift market, and other family-friendly events.

Offering something for everyone, Light Up the Lake has special themed events, including date nights. They also offer cookie kits and scrumptious s’mores to delight all your senses.

Navy Pier’s Centennial Wheel

As part of your Light Up the Lake ticket, you can enjoy a ride on Navy Pier’s Centennial Wheel.

Navy Pier’s Centennial Wheel is an iconic part of the Chicago skyline and a treasured piece of Chicago cultural history. Soaring to heights of nearly 200 feet, the Wheel offers visitors unparalleled, 360-degree views of Chicago and Lake Michigan.

No matter the season, the enclosed gondolas provide a comfortable experience and miraculous city views.

The Polar Express Train Ride

Set to the sounds of the motion picture soundtrack, passengers of The Polar Express relive the magic of the classic story as they are whisked away for a magical one-hour trip to the North Pole.

Once on board, your car hosts work their way through the coach and punch your golden ticket before hot chocolate and delicious Walkers Shortbread are served by dancing chefs.

Passengers then read along with the classic children’s book, The Polar Express, by Chris Van Allsburg.

Amaze Rosemont

Amaze Rosemont

At AMAZE Light Festival in Rosemont, you will find all your favorite holiday traditions. AMAZE Light Festival brings an array of outdoor holiday activities for all ages amongst an immersive display of more than one million holiday lights.

Bring your friends and family to enjoy the thrills of “Polar Peak” tubing, timed light shows, themed-based illuminated worlds, a holiday market, festive food and beverages, a candy shop and more!

Children enjoy visits to Santa’s Workshop, holiday craft making, and festive train rides on the “Artic Express.” Adults will marvel at the stunning displays and festive foods. And both children and adults alike will love winter tubing! The journey through golden lit paths from the North Pole to the Whimsical Forest will be a highlight on your Chicago winter bucket list.


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