The Best Holiday Fun in Chicago

Holidays in Chicago Christmas in Chicago

Heading to Chicago this holiday season? By the time December rolls around, the city is ready for the holidays. The Christmas trees are up, branches are lit with thousands of lights, Menorahs sit in store windows, and wreaths and pine branches line the city streets and buildings. With so many things to see and do in this amazing city, I figured I’d share with you my favorite things to do in my hometown, just before the holidays.

Shopping on Michigan Ave

Holidays in Chicago Christmas in Chicago

In early winter, the retail area on Michigan Avenue becomes a beautiful site with lit trees that line the street. This part of Michigan Avenue is locally known as Chicago’s “Magnificent Mile.” Shoppers walk up and down Michigan Avenue, checking out the higher-end retailers like Apple, Nike, Patagonia, Nordstrom, Chanel, Crate & Barrel, and many more. There are also plenty of restaurants, hotels, and local events that happen here. Just as a side note, being that there are so many tourists and visitors to this area, you will see many street performers as well as homeless people eager for your donations. For more information on shopping and dining on Michigan Avenue, click here to visit their website.


Macy’s on State Street – Walnut Room

Holidays in Chicago Christmas in Chicago
The Walnut Room and its Christmas tree

Macy’s on State Street used to be the Marshall Field’s store as recently as 2005. Despite the name change, the State Street Macy’s kept the infamous Walnut Room, a restaurant rooted in traditions.  The Walnut Room was actually the first restaurant to open within a department store in 1905.

Come up to the 7th floor and dine around a beautifully decorated, giant Christmas tree, in a room adorned with Circassian wood panels and Austrian chandeliers. A more recent local tradition is to have a buffet breakfast here before or slightly after the holidays; even princesses wander the tables to entertain young children and grant holiday wishes. However, as the years have passed, the Walnut Room has become overpriced, overcrowded (jamming way too many tables into its space), and the service and food quality have declined as well. A few years ago, we were told at 9am that the breakfast buffet was over and lunch was then being served. At 9am?

If you do go, be prepared to wait in a line for a table  Even though my experiences were recently negative, yours might be better. Perhaps you can stop by for dessert or simply take a peak in the Walnut Room. Just shopping in the Macy’s State Street store is fun because its history, its opulence, and because it has so many floors of merchandise.

Christkindlmarket Chicago

In Daley Plaza each December, you can find a German style market, complete with small wooden huts that sell goods and treats. At Christkindlmarket, you can dine on traditional German fare, pretzels, spiced cider, spiced nuts, hot cocoa, mulled wine, and more. Looking for unique gifts? Find them here from authentic German merchants. Walk from booth to booth and see items like hand blown glass ornaments, German beer steins, holiday decor, food, and woven knits for sale. Admission is free to get in; all hot drinks receive complementary souvenir mugs as well.

Personally, the biggest downside of Christkindlmarket is how busy it can be. Obviously, a lot depends on the weather, what day you attend, and at what time. If you visit on a weekend, you will be sandwiched into Daley Plaza with thousands of people into an unsettling, claustrophobic situation. You literally cannot move in most places and have to follow the pack of people moving at a snail’s pace. Lines are ridiculously long for food, you have to wait in line 30-45 minutes to pay for merchandise, and just walking from one end to the other can take way too long. I think it’s time they moved the Christkindlmarket to Grant Park or somewhere with more space. TIP: Come earlier in the day, especially on a weekday if you expect to seriously do some shopping! If you’re not visiting downtown, you can visit the market’s second location in Naperville, but expect heavy crowds here on weekends as well. Visit the Christkindlmarket website here.

Ice Skating in Millennium Park

Holidays in Chicago Christmas in Chicago
Skating at Millennium Park

In Millennium Park, near the infamous “Bean” (officially called Cloud Gate), you can take a spin on skates at the seasonal ice skating rink. Lace up your skates and glide along the rink, with a great view of the city and its skyline. Skate for free, but if you need ice skates, rentals are available for $13 Monday-Thursday and $15 on Friday-Sunday and holidays. Open skate hours vary due to lessons so check their website for more information. Hot drinks and snacks are available at the Park Grill Cafe, right next to the rink.

See a Holiday Show

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Joffrey Ballet’s “The Nutcracker” – Image from

Between Chicago, Rosemont, and the rest of the suburbs, there are a multitude of holiday shows to see from November through January. With so many different theaters, dance companies, and the opera, you can certainly find a show to entertain your whole family. Chicago offers some of the best theatrical performances that shouldn’t be missed!


Ice Skating at Maggie Daley Park

Christmas in Chicago, Holidays in Chicago
Maggie Daley Park

Rather than skating on a rink, visitors to Maggie Daley Park can skate on the ribbon of ice that cascades through the park. Twice as long as one loop on a standard rink, the ice ribbon allows skaters to enjoy skating through scenery without getting dizzy from repetitive laps. Ice skate rental is available here, as well as hot drinks. Maggie Daley Park is located in the northeastern corner of Grant Park, right next to Millennium Park. For more information on skating at Maggie Daley Park, click here.

Zoo Lights

Both zoos in Chicago, the Lincoln Park Zoo and Brookfield Zoo, offer a display of holiday lights available from November through early January. At Lincoln Park Zoo, take part in fun family activities like rides and craft making, in addition to ice carving, musical light shows and tasting holiday treats. Similar activities are available at Brookfield Zoo, in addition to magic shows and cookie decorating. Both zoos have daily schedules that offer events on different days. Be sure to check out the Lincoln Park Zoo website as well as the Brookfield Zoo website to get complete information on hours, fees, and other visiting information. The zoos become quite magical at night when they’re transformed into winter wonderlands. It’s a favorite for families with young children.

Museum of Science and Industry

Christmas in Chicago, Holidays in Chicago
Christmas Trees Around the World – Image from

Going to the Museum of Science and Industry in Chicago is fun any time of year. It’s a fantastic museum! What makes visiting during the holidays special is the museum’s Christmas Trees Around the World annual exhibit. Every year, 50 Christmas trees are decorated showcasing holiday traditions from cultures and countries from around the world.  There is also one large decorated tree that marks the center of the exhibit. Walk through a forest of ornamented and lit trees and displays, decorated by numerous volunteers. In addition, live performances within the exhibit are common on weekends. The museum store also sells many of these unique, cultural ornaments, so you can bring home a memory. Follow this link for more information.


Navy Pier’s Winter WonderFest

Christmas in Chicago, Holidays in Chicago
Winter WonderFest – Image from

When the weather is cold outside, come to Navy Pier and attend Chicago’s Fifth Third Bank Winter WonderFest. An indoor playground of sorts, the festival lasts from November 30 through early January. This is a family focused event with activities for children of all ages. In addition to rides and slides, there is a skating rink, bounce house, mini-golf, carousel, and train. Complete with a giant Christmas tree, the indoor fun also includes decorating cookies and photo opportunities with Santa. My children frequented this winter carnival when they were much younger and just loved the games, excitement, and holiday magic that comes alive at this event. Click here to get information about ticketing and hours.

Chicago Foods

Christmas in Chicago, holidays in chicago
Delicious Chicago foods!

I would be remiss if I did not include a bit on Chicago food. Of course, it goes without saying that Chicago has some of the best food around. Of course, deep dish pizza is our speciality. When you’re here, try some famous deep dish at Giordano’s, Lou Malnati’s, Pizzeria Due/Pizzeria Uno, Pequod’s, Pizano’s, and Gino’s East, just to name a few.  In Chicago, there is also Garrett’s popcorn, which has multiple locations throughout the city. Although famous for its “Garrett mix” of cheese and carmel popcorn, there are many other hand crafted flavors to choose from. Other famous foods include popcorn at Nuts on Clark, hotdogs at Portillo’s and Superdawg, Italian beef at Portillo’s or Al’s Italian Beef, Frango mints available at Macy’s, cheesecake made by Eli’s Famous Cheesecake, and doughnuts at the Doughnut Vault. With so many delicious places to dine at, you’ll be hard pressed to find one you don’t like.

Despite the cold weather and snowy winters, Chicago can become a magical city in December. I hope you’ll come for a winter visit!

Happy Travels!


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