The holiday season kicks off early in Chicago, giving you plenty of time to enjoy the festive spirit in the Windy City. When we visited Chicago this summer during our midwest road trip, it was hot and crowded. It was much colder when I returned a couple of weeks ago as the guest of CityPASS and Choose Chicago. But I was still surprised to find so many ways to celebrate Christmas in Chicago that started before Thanksgiving.

I love visiting cities around the holidays. There is something about seeing the trees decorated, popping into Christmas markets, and checking out the holiday shop windows that just puts me in the mood for Christmas (and Hanukkah).

I have been to LondonNYC, Philadelphia, and many other places along the East Coast, but I never really thought about Chicago as a big holiday destination. So I was pleasantly surprised to take part in so many holiday traditions that Chicagoans hold dear and get to experience the city in a different way (and temperature.)

Chicago Christmas tree lighting

7 Ways to Celebrate Christmas in Chicago

My recent trip to Chicago was hosted by CityPASS and Choose Chicago. We were hosted at the Four Seasons Chicago. All opinions are my own.

See the Tree(s)

Official Chicago Tree Lighting

Chicago tree lighting fireworks

In NYC, everyone makes the pilgrimage to see “The Tree” in Rockefeller Center. In Chicago, the famous tree is in Millennium Park. The official tree lighting happens in November (check the Choose Chicago website for dates), but it remains lit throughout the season. The tree light includes performances by special guests and introductions by local officials.

After performances the massive tree is lit, followed by fireworks and Christmas Caroling at Cloud Gate (also known and “The Bean.”) Carolning at the Bean also takes place throughout the holiday season.

If you want to attend the tree lighting, I would recommend arriving early to get a prime spot, just don’t be surprised by street closures in the area. Even if you aren’t there for the official tree lighting ceremonies, you can still see the tree throughout the season.

Christmas Around the World

MSI Festival of trees

From mid-November through early January, the Museum of Science and Industry brings “Christmas Around the World” and “Holidays of Light” to Chicago with a festival of trees. In addition to the 45-foot Grand Tree in the Rotunda, there are also 50 smaller trees that represent cultures and holiday traditions from around the world.

Museum of Science and industry christmas trees

I loved looking at all the various trees to represent different countries. I was also appreciative of the inclusion of other seasonal celebrations such as Diwali, Kwanza, Hanukkah, and Winter Solstice. If you hang out by the Grand Tree long enough, you can also experience some indoor “snow.”

900 North Michigan Shops

900 North Michigan shops

The 900 North Michigan Shops also does an elaborate tree lighting ceremony, complete with VIP tickets that include food and drinks. The celebration offers pictures with Santa, tea with Mrs. Claus, children’s activities, food from the newly-opened Aster Food Hall, and selfies with an Elf of the Shelf.

More Christmas Tree Celebrations

Of course there are many other fun places to find Christmas trees, holiday lights, and fun for the holidays in and around Chicago. You can enjoy ZooLights at the Lincoln Park Zoo, Illumination: Tree Lights at Morton Arboretum, and you can even ride the CTA “Holiday Train.”

There is also the Winter WonderFest at Navy Pier, when Festival Hall transforms into a winter wonderland full of rides, giant slides, indoor ice skating, and holiday decor.

Catch a Parade

Magnificent Mile parade Nutcracker

Magnificent Mile Lights Festival kicks off the holiday season with the annual Lights Festival parade. When I attended, Mickey and Minnie Mouse kicked things off and they were followed by marching bands, floats from local businesses like Garrett Popcorn, and other performers.

As the parade progresses along the route, over a million lights are lit along Michigan Avenue. The parade wraps up with an appearance from Santa Claus, of course, followed by fireworks over the river.

Magnificent Mile parade Santa Sleigh

If you want a front row space to view the parade, you will need to get there very early and dress very warm. If you miss the Lights Festival parade, there is also Uncle Dan’s Thanksgiving Day Parade.

Lunch in the Walnut Room

Macys clock in Chicago

Macy’s is a must-do stop when visiting Chicago for the holidays. This former Marshall Fields on State Street has some of the better decorated holiday windows and the holiday decor on sale on the Seventh Floor is not to be beat.

Walnut Room Macy's Christmas tree

But one of the famous holiday traditions for Chicago families is a meal in the Walnut Room on the Seventh Floor of Macy’s. From the time of the Giant Tree lighting through early January, The Walnut Room ushers in the holidays with a festive meal.

Chicago Christmas Market

Christkindlmarket merchandise

From mid-November through Christmas Eve, Daley Plaza in downtown Chicago converts into a traditional holiday market, based on the Christmas Market in Nuremberg, Germany.

They do a good job in keeping it authentic with many German artisans displaying their wares, including ornaments, knit hats, cuckoo clocks, and other handicrafts. You can also enjoy spiced wine, strudel, sausages, roasted nuts, hot cocoa, warm apple cider, and other traditional treats. You can purchase a souvenir mug and receive discounted refills (year after year.)

The Chicago Christkindlmarket has been a tradition for over 20 years so expect it to get very crowded, especially on the weekends. You will probably want to get there early to avoid the crowds, otherwise you can expect long lines at the stalls.

Go Ice Skating

Maggie Daley skating ribbon
Image courtesy of Choose Chicago

If you are willing to brave the cold, there are a few places in the city where you can go ice skating. The McCormick Tribune Ice Rink in Millennium Park offers great views of the city skyline and “The Bean” (aka Cloud Gate.) The best news? Admission is free (you just need to pay to rent skates if you need them.)

More advanced skaters will enjoy the unique experience of skating on the Maggie Daley Skating Ribbon. This ribbon curves its way through Maggie Daley Park, with inclines and declines along the way. Admission is also free. Just keep in mind that the surface requires an extra-long time to resurface and will result in the ice closing for the Zamboni for an hour or more so check the schedule in advance.

You can also ice skate on Navy Pier at the Winter WonderFest and at the Sky Rink at the Peninsula Hotel, but you will have to pay for both of those!

Take a Tour

Chicago Christkindlmarket

There are a number of different holiday lights tours, including a Trolley Tour, Segway tour, dinner cruises, and walking tours. However, if you want to combine a little history with holiday cheer, check out the “Drinks, Daleys and Dead Guys” walking tour from Chicago Detours.

This walking tour is largely indoors and includes a couple of drinks for some holiday cheer. You start off with the Tom and Jerry cocktail at the historic Miller’s Pub, learn how Mayor Richard J. Daley saved the Christmas parade, and stop into Macy’s Walnut Room for a look at the tree. The tour finishes up just outside of the Christkindlmarket.

See a Show

There are over 200 theaters in Chicago, spread out between neighborhoods with everything from big Broadway productions like Hamilton to smaller theater troupes. Charles Dickens’ classic tale of A Christmas Carol is now in its 41st year.

This year the Goodman Theatre is also debuting David Sedaris’ irreverent The Santaland Diaries. Other holiday favorites include the Joffrey Ballet’s performance of The Nutcracker. Families may also like The Beatrix Potter Holiday Tea Party at the Chicago Children’s Theatre at the Station.

To save some money, look for half-price theatre tickets on HotTix.org. And of course, if you aren’t interested in a holiday show, it is surprisingly easy to get tickets to see Hamilton in Chicago and it makes a great holiday treat!

Where to Stay in Chicago for Christmas

There are so many fabulous hotels in Chicago, but it really helps to be centrally-located near the Magnificent Mile. My friend Kirsten also has a great guide for where to stay in Chicago with kids.

Four Seasons Chicago

Four Seasons Chicago

For this holiday trip, I was hosted at the Four Seasons Chicago, on E. Delaware Place near North Michigan Avenue. As always with the Four Seasons, the service was outstanding and the rooms were luxurious and comfortable.

I had a lake view room on the 36th floor with excellent views of Lake Michigan and the Hancock Building. It was so cozy to return after a cold evening out, curl up in my robe under layers of covers and gaze out at the beautiful night skyline.

Four Seasons Chicago room 3615

I love the Four Seasons for families because they really roll out the red carpet for their youngest guests. At check in, kids will use the special step stool to register at the desk. They then receive a Sammy the Skyscraper Passport booklet. Throughout their stay, they can complete an activity at the spa, restaurant, bell desk, etc. to receive a stamp. A full passport earns them a free ice cream!

Children also receive a choice of toy from the treasure chest at check-in, a special welcome amenity, a kid’s “shoe shine” service (which returns their shoes with a special Four Seasons’ charm and new shoelaces), and selfie frames at the front desk.

Plus, they have access to the Kids Clubroom featuring foosball, air hockey, Nintendo Wii, books, and toys, as well as the 50-foot indoor pool (featured in Home Alone 2).

For the holidays, the Four Seasons Chicago is also offering a guided craft-making station from 11am-3pm in the Kids’ Club for kids ages two and up.

Families looking for a special way to celebrate the holidays can enjoy the Family Fun in the City package with daily breakfast for two, complimentary meals from the children’s menu for those under five, a movie of their choice (with popcorn and sodas delivered to the room), and even a visit from the ice cream man between 3-6pm (once per stay.)

The Gwen

The Gwen

If you want to be a bit more centrally located, this summer Hannah and I used Marriott points to stay at The Gwen, a Luxury Collection property. The vibe was luxurious but hip, definitely not a stuffy luxury hotel, but also not quite as kid-friendly feeling as the Four Seasons. Still, the rooms were spacious and very well-appointed and designed.

We both loved how quiet it was at The Gwen and really enjoyed the luxury amenities. We only had breakfast at the hotel, as it was included as Marriott Platinum Elite members. The location of the Gwen was perfect for walking to the theater, shops, and Millennium Park.

For the holidays, The Gwen has introduced an iceless Curling Rink and Curling Cabin on the fifth-floor Upstairs of the Gwen. The hotel’s outdoor terrace is transformed into a seasonally splendid winter getaway.

The Gwen curling rink and curling cabin
The Gwen Curling Rink and Curling Cabin. Image courtesy of The Gwen.

The custom-designed, iceless Curling Rink offers guests to try their hand at the winter sport that originating from Scotland, in which players slide stones on a sheet of ice or a lane towards a target.

Additionally, the custom-made wooden Curling Cabin offers respite from the cold, where guests can cozy up by the electric fireplace and enjoy the Alpine-inspired menu from Executive Chef Matt Jergens and warm winter cocktails from The Gwen’s beverage team. Reservations for the Curling Rink and Cabin are available via OpenTable.

The Radisson Blu Aqua Chicago

The Radisson Blu offers two buffet seatings of a Santa Brunch on December 14 , 2019 from 9 – 11:30 am and 12:30 – 3 pm. The brunch includes bounce houses, trains, a petting zoo and plenty of arts and crafts to enjoy throughout the day. Each table will be entered to win a weekend stay at the Blu.

The Talbott Hotel

Holiday cheer extends to hotel suites at The Talbott Hotel. Guests who book a junior suite at The Talbott Chicago for stays in November and December and enjoy complimentary breakfast and coffee, as well as free pick-up of your shopping bags anywhere on North Michigan Avenue and gift wrapping upon your return!

Families can also make a little one’s dreams come true with The Talbott’s American Girl DREAM Package, which includes a personalized welcome letter and stationery, milk & cookies turn-down service, doll robe and slipper set, breakfast in bed for two, and more!

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Festive things to do in Chicago at Christmas from ice skating, parades, tree lightings, shows, and more. #chicago #christmas
Christmas in Chicago

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