cat in the hat balloon float at a thanksgiving parade

Best Things to do on Thanksgiving Weekend in the Chicago Area (2023)

Turkey Day is almost here, which means the official launch of the holiday season! There are tons of fun things to do in downtown Chicago and around the Windy City this time of year. Even if you prefer staying home, we have some ideas for great things to do to spend quality time with your family. Here are our suggestions for family-friendly events and fun activities to do over the holiday weekend!

Chicago Thanksgiving Parade

November 23, 2023 | 8:00am-11:00am Parade route: State Street from Ida B. Wells Dr. to E. Randolph St.

Don’t miss one of the biggest Thanksgiving Parades in the United States. The Chicago Thanksgiving Day Parade stretches down State Street from Ida B. Wells Drive to Randolph Street. There will be festive floats, huge helium-filled balloons, live music, marching bands, and live performances that the kids will love. Don’t miss the special guest: Santa Claus!

Even if you can’t make it in person, you can live stream the performance or watch it on television while you make your cranberry sauce and sweet potatoes!

The Turkey Trot

November 23, 2023 (Some of the suburban races are on different days. Click the links below for more information)

There are many “Turkey Trots’ happening on Thanksgiving morning, and participating could become a new holiday tradition for your family! The Turkey Trot in Chicago benefits the Greater Chicago Food Depository and takes place in Lincoln Park.

Kids as young as 2 can participate in the “Plymouth Rock Ramble” which starts at 11:00 am. Each registered kid will receive a t-shirt and a medal.

Everyone can attend the Turkey Trot Tailgate after the race for games, food, and activities. Other Turkey Trots to check out are in Shaumburg, North Shore, Lincolnwood, Elmhurst, and Naperville.

Go Out to Eat

Don’t feel like cooking this Thanksgiving Dinner? Skip the prep work and dirty dishes, and head to one of these great Chicago restaurants for your holiday meal..

Not all of these are open on Thanksgiving Day, but they will be open the rest of the weekend. Here are the best kid-friendly restaurants in Chicago if you want to enjoy a nice meal between shopping and getting in the holiday spirit.

A family shopping at a german Christmas market stand
The Christkindle Market has 3 locations this year!

Do Some Holiday Shopping

Black Friday is almost here, which means it’s time to do some holiday shopping! It can be fun to involve your kids in buying gifts for others and allowing them to discover the joy of putting a lot of thought into a gift. Below are some unique and interesting places to do some holiday shopping this season!


A great way to get in the holiday spirit in the great city of Chicago is to visit the Christkindlemarket (the Christmas market). They have a unique selection of Christmas ornaments, novelty mugs, and artisan treasures. One of the most charming European traditions has become one of Chicago’s most treasured holiday events, and now there are three locations.

This year, your kids can sip hot chocolate in a souvenir boot in Daley Plaza, Aurora, or Gallagher Way in Wrigleyville. If you have small kids, I highly recommend checking out the Gallagher Way location. They essentially turn Wrigley Field into a winter carnival complete with Santa’s Workshop, an ice skating rink, a carousel, rides, and games! It’ll be a great time for the whole family!


Sure, Michigan Avenue is one of the biggest tourist attractions in Chicago, but it’s also super fun around the holidays. The hustle and bustle of the Magnificent Mile can really put you in the holiday spirit. The American Girl doll store has lots of holiday events, and the Lego store is nearby too!

State Street is another fun place to explore for some holiday shopping, and the best part is checking out the Macy’s Department Store Window displays. Fun fact: this Macy’s location was once the site of the Marshall Field Department Store that was built for the 1893 World’s Fair. It has a long history, and it’s become a holiday tradition to grab a snack and see the giant tree in the Walnut Room. If the Walnut Room is booked, the 7th floor of Macy’s has another restaurant!

25 Best Toy Stores in the Chicago Area

One of the best things about Chicago is the character of the many stores across the city. Times are tough for many local shops right now, and Chicago has lots of cool toy stores for your holiday shopping. Small business Saturday is about supporting small businesses, so make sure you show these shops some love on Saturday!

family ice skating

Go Ice Skating

Ice Skating is the perfect way to spread some holiday cheer! There are plenty of outdoor ice rinks around Chicago, and even some indoor ones as well! Here are some great ones to check out!

McCormick Tribune Ice Rink

The McCormick Tribune ice skating rink is located in Millennium Park, so it’s a great place to go ice skating after some holiday shopping or checking out the Christkindlemarket in Daley Plaza. It is FREE to ice skate, but advance registration is required. More details will be announced in the coming weeks, but they even have some free skating lessons! Ice skate rental is $10 a pair or you can bring your own skates.

Winterland Ice Rink

This year, you can have the opportunity to go ice skating in Wrigley Field! Starting November 18, Wrigley will turn into “Winterland” and feature an ice skating rink and rides!

Maggie Daley Park Ice Skating Ribbon

Maggie Daley Park is a super unique ice skating rink in the shape of a ribbon for breast cancer awareness. It’s located in Maggie Daley Park, right next to Millenium Park. Reservations are not required but strongly recommended. Prices depend on the date and time and whether you need to rent skates.

Navy Pier

Navy Pier is hosting their annual indoor light display that includes a whimsical ice skating rink, a birch tree maze, and visits from Santa. This is a great option if it’s too cold to skate outside!

See a Show

The theater can be such an exciting experience for kids, and there are lots of great kid-friendly plays and musicals showing in Chicago in November! Below is a list of some family-friendly plays and musicals, but be sure to check out the Events page for a full list.

A Christmas Carol

November 18- December 31, 20223| Run Time: 2 Hours with 1 15-minute intermission Recommended Ages: 6 +, Children under 5 are not permitted in the theater

The Charles Dickens’ classic runs every year at the Goodman Theater, each time with a different twist. It’s a great tradition for the whole family!

The Beatrix Potter Holiday Tea Party

November 4-December 24, 2023 | Run Time: 1 Hour Recommended Ages: 2-6

Four Beatrix Potter favorites gather for a tea party in this puppet and trunk show.

Indoor Experiences

When the weather gets colder, it’s an ideal time to check out some of Chicago’s world-class museums and other indoor attractions. There are several fun events and free days coming up in November!

Museum of Science and Industry

The Museum of Science and Industry is celebrating its 80th anniversary of the “Christmas Around the World and Holidays of Light” exhibit that displays more than 50 Christmas trees, each representing a different country. The trees are decorated to show the holiday customs of different cultures around the world. Fun Fact: this exhibit started in 1942 with a single tree. The tree was decorated differently every day for 12 days to honor the countries fighting with the United States in World War 2.

Immersive Nutcracker

Don’t miss this sensory, immersive experience. The Nutcracker is taking over the Lighthouse ArtSpace, and it will surely feel like a winter miracle without the cold!

ZooLights at the Lincoln Park Zoo

Enjoy Holiday Lights

The large popular light shows at the Lincoln Park Zoo, Chicago Botanic Garden, and Merchandise Mart are just scratching the surface of the cool light displays around Chicago. Check out our complete guide on holiday decorations and light displays to check out in the Chicago area!

Put up the Christmas Tree

We have a fake tree in my house, but I definitely plan on listening to some Christmas Music, watching Home Alone, and putting up the Christmas Tree on Thanksgiving weekend!

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