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.)

7 Ways to Celebrate Christmas in Chicago

Chicago Christmas tree lighting

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)

In NYC, everyone makes the pilgrimage to see “The Tree” in Rockefeller Center. In Chicago, the famous tree is in Millennium Park. For 2018, I was there on November 16th (check with Choose Chicago for future dates) for the 105th anniversary of the City of Chicago’s Christmas Tree Lighting ceremony. The ceremony was hosted by Miguel Cervantes, Hamilton in the Chicago Company at Broadway.

Chicago Hamilton at Christmas tree lighting ceremony

After performances from local theater performers and a Disney Channel star, the 60-foot tree was lit, followed by fireworks and Christmas Caroling at Cloud Gate (also known and “The Bean.”) 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.

Chicago Christmas tree lighting

Chicago tree lighting fireworks

From November 15, 2018 through January 6, 2019, the Museum of Science and Industry brings “Christmas Around the World” 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.

MSI Festival of 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.”

Museum of Science and industry christmas trees

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.

900 North Michigan shops

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.”

Take an elfie

There is also the Winter WonderFest at Navy Pier from November 30, 2018 through January 6, 2019. 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 kicked off the holiday season with the annual Lights Festival parade. This year Mickey and Minnie Mouse kicked things off and they were followed by marching bands, floats from local businesses like Garrett Popcorn, and other performers.

Garrett popcorn float

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 treeBut 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 January 6, 2019, The Walnut Room ushers in the holidays with a festive meal.

Walnut Room dessert buffet

New for 2018-2019, they are now offering a buffet in addition to an a la carte menu. This option moves through the wait list faster (reservations are highly recommended but also very limited!) The buffet is $25.95 for adults and $13.95 for kids 12 and under. With the buffet you not only get to try their famous chicken pot pie, but also plenty of other treats and holiday desserts.

Chicago Christmas Market

Christkindlmarket booths

From November 16, 2018 through December 24, 2018, 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.)

Christkindlmarket merchandise

The Chicago Christkindlmarket has been a tradition for 23 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

Millennium Park ice rink

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 with a $12 skate rental fee on weekdays and $14 on weekends and holidays. 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.

Maggie Daley skating ribbon

Image courtesy of Choose Chicago

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

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.

Chicago Christkindlmarket

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.

Hannah at Hamilton in Chicago

To save some money, look for half-price theatre tickets on 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

There are so many fabulous hotels in Chicago, but it really helps to be centrally-located near the Magnificent Mile.

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.

Four Seasons Chicago room 3615

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 lake view

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.)

Four Seasons night view

The Allium Restaurant downstairs offers a great mix of healthy options and high-end comfort options, like the chef’s pick, organic buttermilk fried chicken.

Allium fried chicken

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.

The Gwen

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.


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

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