Chicago turns into a winter wonderland during the holidays – from the world-famous Christkindlmarket to the Macy’s State Street Holiday Windows, there’s no better time to plan a visit. Pack your bags for the ultimate family getaway to Chicago this holiday season and be sure to include all of these must-see destinations.


Experience the Magical World of Dr. Seuss

The Dr. Seuss Experience is in Chicago for a limited time this winter and tickets are on sale now. And because we are HUGE fans of Dr. Seuss AND Chicago, we want to give one lucky family 4 FREE TICKETS to experience all of the silly family fun. 

Where: Water Tower Place, 835 N. Michigan Avenue, Ste. 100, Chicago

When: October 8, 2021 – January 2, 2022

Cost: Tickets start at $23, children under 12 months are free

Shop the Christkindlemarkets

The Christkindlmarket Chicago is the most authentic traditional holiday market of its kind outside of Europe, offering a unique outdoor shopping experience, family-friendly events & intercultural activities. The Daley Plaza market is located downtown in the Loop. A second market is located at Winterland in Wrigleyville, which is home to an 8000-sq-foot ice skating rink, holiday movies, and visits with Santa! 

Where: Daley Plaza, 50 W. Washington Street, Chicago & Gallagher Way, 3635 N. Clark Street, Chicago

When: November 19 – December 24 (Daley Plaza); November 19 – December 31 (Wrigleyville)

Cost: Admission is FREE

See the Lights at Lincoln Park Zoo

Just north of downtown, check out the Lincoln Park Zoo ZooLights which features light shows, an 18-foot holiday tree, and hundreds of luminous displays & experiences! 

Where: Lincoln Park Zoo, 2400 N. Cannon Drive, Chicago

When: 4 p.m. – 10 p.m. on select dates from November 19, 2021 – January 2, 2022

Cost: Monday/Tuesday is FREE, Wednesday-Sunday tickets are $5

Enjoy Holiday Cheer at Millennium Park

Millennium Park is home to Chicago’s “official” Christmas Tree and the Millennium Park Holiday Sing-Along. The park also features the beautiful McCormick Tribune Ice Rink which is FREE but requires advanced reservations. Or head next door to Maggie Daley Park to experience the one-of-a-kind skating ribbon, which curves through the park’s whimsical landscape. 

Where: Millennium Park near the intersection of Michigan Ave. & Washington St.

When: November 19, 2021 – January 9, 2022, the Holiday Sing-along is every Friday beginning on Nov. 26 – Dec. 17

Cost: Admission is FREE, reservations are required to skate at both ice rinks

See the Lightscape at the Chicago Botanic Garden

The Chicago Botanic Garden is transformed into a holiday light wonderland walk for Lightscape! From singing trees and magical light shows to the Winter Cathedral, all of which are just some of the immersive, lit-up magic you’ll experience. 

Where: 1000 Lake Cook Road, Glencoe

When: November 12, 2021 – January 2, 2022

Cost: Prices start at $12/person, kids under 3 are free

Take a Ride on the Santa Express

Hop on one of the countries few authentic Polar Express train rides that depart from the iconic Union Station. Or take a ride on the nation’s only remaining elevated train (the “L”) and experience the CTA Holiday Train (or Bus)

Where: Click the links above for location details

When: Polar Express Train: December 3 – December 31; CTA Holiday Train: Begins the day after Thanksgiving

Cost: Polar Express: Tickets start at $57/person

Walk the Macy’s Holiday Windows

The Holiday Windows at Macy’s on State Street has been a longtime tradition of Chicagoans and tourists since 1944! Walk the entire block to see each incredibly designed holiday window display.

Where: Macy’s, 111 N State St., Chicago (walk around the block to see the entire display)

When: November 1 – December 31

Cost: FREE

Dine at the World-famous Walnut Room

After checking out the Macy’s window displays, head inside to experience the Walnut Room where you’ll find The Great Tree. This Chicago tradition has been going on since 1907 and features a beautiful restaurant where diners enjoy their meal surrounded by the incredible Macy’s Christmas Tree. It’s a truly magical experience! 

Where: Macy’s, 111 N State St., Chicago

When: November 7, 2020 – January 3, 2021 (reservations are required)

Cost: The holiday menu features a three-course meal for $49.95/person for adults. And $19.95 for kids 12 and under. 

See the Lights + Shop the Magnificant Mile

Take a stroll down the Magnificant Mile to see the 1 million lights that illuminate the trees! You’ll also find holiday window displays and special events happening each weekend. The Mag Mile is also the best place to get any last-minute holiday shopping done and with stores like The American Girl Store + The LEGO Store, you’ll be sure to find everything you need. 

Where: N. Michigan Avenue between Oak Street & the Chicago River

When: Kicks off on November 20

Cost: FREE

Visit the Museum of Science + Industry Holiday Exhibit 

Christmas Around the World & Holiday of Light at the Museum of Science + Industry is an annual celebration that features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 50 trees and displays that represent the holiday traditions from cultures around the globe. Santa is also on-site for family photos! 

Where: Museum of Science + Industry, 5700 S Lake Shore Dr, Chicago

When: November 17 – January 3

Cost: Tickets start at $12.95/person

Explore Winter Wonderfest at Navy Pier

Although no official dates have been announced for Winter Wonderfest at Navy Pier, keep this one on your radar! Experience the city’s biggest and best indoor winter playground and join the millions of families who have made it a part of their annual holiday tradition! It features 170,000 square feet of carnival rides, giant slides, holiday-themed activities, an indoor ice skating rink, and more.

Where: Navy Pier, 600 E Grand Ave, Chicago

When: Dates yet to be announced

Cost: Tickets start at $10/person

*Please be aware that certain attractions and destinations may still be impacted by Covid-19 restrictions. We recommend contacting specific locations to help you better plan your visit.  


There are tons of great neighborhoods to stay in during a visit to Chicago, so it’s hard to recommend just a few places but these hotels are family-friendly and in the best locations for getting to some of the most popular Chicago destinations. 

Embassy Suites are some of the best hotels for families – offering suites with separate sleeping and living areas, free breakfast, and an on-site pool. The hotel offers views of Lake Michigan and is conveniently located within walking distance to Navy Pier and Millennium Park. 

Stay Pineapple is a fun boutique hotel located in the heart of downtown and within walking distance of Millennium Park, Lake Michigan, and the Mag. Mile. For families, suites are available with separate living rooms and sleeper sofas. 

This budget-friendly hotel offers a great location, an indoor pool, and separate living and sleeping suites. 

The Four Seasons knows how to cater to kids – The Family Experience is the ultimate kid-friendly way to stay and includes a “welcome” toy at check-in, in-room visits from the ice cream man, and FREE access to the 32nd Floor Kids Club Room which has games, crafts, and movies.  

Located on the beautiful Chicago River with views of Lake Michigan, you can’t find a much better location! The Kids Suite at the Swissotel is worth the splurge and includes a two-room suite, complimentary movies, and FREE breakfast! Best of all, the signature Swissotel Kids Room is stuffed with age-appropriate toys, books, games, and more. 


Eating in Chicago is an experience in itself and Chicagoans take their food very seriously! We literally argue over who’s got the best beef sandwiches, the most authentic “Chicago dogs” (hotdog), and whether deep dish or tavern-style pizza is Chicago’s signature pizza! No visit to the Windy City is complete without grabbing a bite to eat from these delicious Chicago dining establishments.

Chicago-Style Hotdogs

  • Chicago’s hotdog game is no joke and a visit to the city isn’t complete without grabbing a Chicago-style dog! Superdawg Drive-in and Portillos are some of the more “nationally” recognized hotdog joints while Dowtown Dogs and Fast Track are kid-friendly and conveniently located downtown. Whatever you do, DO NOT ask for ketchup on your hotdog – you legit may get yelled at. 

Chicago Pizza

Italian Beef Sandwiches

  • An Italian beef sandwich is another essential Chicago meal. Order it “hot (or sweet, or both) & dipped” and be sure to assume “the Italian stance” so the juices of the sandwich don’t drip all over you! Conveniently located, Al’s Beef in Little Italy, Luke’s, and Buona Beef are great places to pick up Chicago’s favorite sandwich. 

Authentic Mexican Food

Food Hall

Italian Food

  • With the third-largest Italian population in the country, Chicago is not messing around when it comes to authentic Italian American food. Italian Village is the oldest Italian restaurant in the city, conveniently located in the heart of downtown, and a place my family has been visiting since I was little. Forno Rosso Pizzeria, Monteverde, and Eataly Chicago are all kid-friendly and delicious. 

Fun Themed Restaurants 

*Please be aware that certain attractions and destinations may still be impacted by Covid-19 restrictions. We recommend contacting specific locations to help you better plan your visit.  

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