2021 Chicago Christmas Trip Planner: Find the Best Holiday Fun

2021 Chicago Christmas Trip Planner

Chicago at Christmastime is a Favorite Family Tradition

In our family, we love all holidays and the traditions that come with them.

Just about every holiday at our house comes with a family tradition: we dine on green milk with our cereal on St. Patrick’s Day and enjoy egg hunts on Easter morning.

When the Christmas season rolls around, we upgrade our tradition game and embrace all things merry and jolly.

We take an annual holiday light cruise around town, make chocolate-covered pretzels, visit Santa, enjoy an elaborate advent calendar, and have fondue for dinner on Christmas Eve. 

The list could go on and on, but a Chicago Christmas is hands down my favorite family tradition.

My husband and I have been visiting Chicago for Christmas since before we had kids. 

Just thinking about walking down Michigan Avenue after dark with the holiday lights glowing gets me giddy for Christmas.

A stroll downtown includes street performers playing Christmas songs, the hustle and bustle of holiday shoppers, lighted garlands and trees everywhere and store windows decorated to the max.

Considering a new tradition for your holiday season? Read on for why Chicago is the perfect Christmas destination:

Kids Looking at Skyscrapers during Chicago Christmas

14 Best Chicago Christmas Things to Do

If you’re headed to the Windy City this holiday season, here are the best things to do in Chicago during this merry time of year:

1) Make Reservations at JoJo’s River North Location for Holiday Shakes & Photo Ops

23 W Hubbard St, Chicago, IL 60654

They have a walk-up window or you can make reservations for a table in the Christmas-themed popup room complete with an old fashioned truck and Christmas trees.

They also serve food, hot chocolate, and a milk and cookie flight.

Pro Tip:
Expect to pay a $10 table fee if you want to sit in the Christmas area.

Christmas-themed shakes are available at JoJo’s Shake Bar.
This place is perfect for photos!
Milk + Cookie Flight comes with four freshly baked cookies and house-made milks

2) See the ZooLights at Lincoln Park Zoo

Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614

ZooLights runs November 19, 2021 – January 2, 2022 this season from 4 -10 pm daily. Closed Dec 24 & 25.

The Lincoln Park Zoo becomes a holiday winter wonderland as it lights up with over 2.5 million Christmas lights! It’s truly a sight to see and my kids’ favorite thing to do in Chicago at Christmas.

Zoolights includes ice sculptures, lighted tunnels, character displays, and 18-foot holiday tree, and a musical light show.

The animal exhibits are open and we’ve found the animals to be very active in the evening.

Tickets are required for all guests, including infants and children. Monday and Tuesday nights are free and Wednesday-Sunday tickets are $5.

Sensory-Friendly Nights are Nov 19 and Dec 13, 2021.

Pro Tips:
– Arrive at dusk or try to go on a weekday to avoid the crowds.
– Admission is free at Lincoln Park Zoo, but ZooLights is a ticketed event and there is a fee. Buy tickets in advance online.
– Parking can get pricey – consider public transit or a car service. 
– You may want to buy “light up Christmas necklaces” for your kids ahead of time at a dollar store. They are pricey at the zoo and every kid wants one.

Zoo Lights sign lit up at night in Chicago
ZooLights at Lincoln Park Zoo is a highlight of Chicago at Christmas
kids smiling outside giraffe exhibit at the zoo
Animals are out and active during ZooLights

3) Skate the McCormick Tribune Ice Rink at Millennium Park

Michigan Ave. between Washington & Madison Streets, Chicago, IL 60602

Located on Michigan Avenue, this skating experience is one your family will remember. Be sure to capture some photos here, as your little skaters are surrounded by holiday decorations and skyscrapers in the heart of downtown Chicago.

Bring your own skates and skate for free (rentals are also available).

Make sure to stop by “The Bean” for a few photos as well. During the holidays, you often find carolers gathered nearby.

ice skating rink in downtown Chicago
McCormick Tribune Ice Rink at Millennium Park
Chicago Cloud Gate Bean
Obligatory Tourist Pic at Cloud Gate

4) Try the Ice Skating Ribbon & Epic Slides at Maggie Daley Park

337 E Randolph St, Chicago, IL 60601

Skating Ribbon opens November 19, 2021, weather permitting.

After visiting Millennium Park, head to nearby Maggie Daley Park.

Both Maggie Daley Park and Millennium Park sit within Grant Park on Chicago’s waterfront. Located near Museum Campus, the area is a magnet for locals and tourists alike.

This park changes with the seasons. In the wintertime, visit the Ice Skating Ribbon. The quarter-mile loop’s gentle slope is covered with ice and open for skating.

Tickets for ice skating go on sale starting November 8, 2021. Rentals are available.

Also at Maggie Daley Park: The Play Garden. Do not skip this!

Filled with amazing playscapes for all ages, the highlight for us is the Slide Crater. Towers, suspension bridge, and a multude of slides converge on the crater for an amazing afternoon of play. And it’s free!

My kids love it here and would probably be happy to spend an entire afternoon exploring, climbing and swinging

Footbridge from Millennium Park to Maggie Daley Park takes you over Columbus Drive
Ice Skating Ribbon in Maggie Daley Park
Skate rentals are available
Maggie Daley Park at the Slide Crater

5) Experience Christmas Around The World at the Museum of Science and Industry

5700 S. DuSable, Lake Shore Dr, Chicago, IL 60637

Holiday exhibit opens November 17, 2021 and runs through January 3, 2022.

This annual Christmas exhibit at the Museum of Science and Industry runs from mid-November through January.

The showcase is a 45-foot floor to ceiling, Grand Tree surrounded by 50 smaller trees representing Chicago’s diversity, and showcasing their holiday traditions.

In 2021, they are also celebrating the golden age of travel with themed décor and a spotlight on their newly reimagined Pioneer Zephyr train and Take Flight’s 727.

The museum is stocked with tons of kid-friendly exhibits, so plan to spend the better part of a day exploring. We love it here because there are a ton of hands-on experiences.  

Photos with Santa are $30 per group and are available on certain days. Separate tickets are required.

Pro Tip:
The Museum of Science and Industry has a reciprocal membership with the Air Zoo.
The membership offers two adults and up to four children under 18 living in their home free basic admission to the museum. You must have your current Air Zoo Membership Card, photo ID and proof of residency.

Chicago Museum of Science and Industry at Christmas
It’s exciting when it snows inside of the museum!
Chicago Museum of Science and Industry
U-505 Submarine – experience a real German submarine, housed indoors.

6) Oooh and Ahhh at Macy’s Holiday Window Display on State Street.

111 N State St, Chicago, IL 60602

Mid-November through January, the Macy’s storefront windows on State Street are transformed into a magical holiday display with elaborate and imaginative themed windows.

Our family loves to check out each one and then we vote on the winner! 

Macy's Christmas Window Decorations in Chicago
The Sidewalk at Macy’s State Street Location is Dressed for the Holidays
Macy's Holiday Windows
Captivating Window Displays Line the Street

7) Dine at the Walnut Room in Macy’s

111 N State St, Chicago, IL 60602

Head into Macy’s flagship store to warm up and have lunch at the foot of the beautifully decorated 45 foot tree, with over 25,000 lights.

The world-famous Walnut Room was the first restaurant ever opened in a department store. With Circassian wood paneling imported from Russia and Austrian chandeliers, the 17,000 square foot dining room is both elegant and comfortable.

Conveniently located in the heart of the Chicago theatre district, the Walnut Room is an excellent choice to take a break from shopping or for a meal and a glass of wine before the show.

Pro Tips:
– Make reservations ahead of time for lunch. Slots are available starting November 6 in 2021.
– Lunch is a wonderful experience and a nice way to save on the budget.

Walnut Room Christmas Tree
The Walnut Room’s décor is spectacular
Inside Macys on State Street in Chicago
The department store is decked out for Christmas as well

8) Make an Appointment to See Santa

November 6 – December 24, 2021
111 N State St, Chicago, IL 60602

You can make a reservation online 5 days in advance of your visit.

Santaland is for children of all ages, but reservations can only be made by adults age 18 and older.

Where: 5th floor, Santaland in Macy’s on State Street

9) Shop the Christkindlmarket

November 19 – December 24, 2021
Daley Plaza, 50 W Washington St, Chicago, IL 60602

Looking for a one of a kind gift? Christkindlmarket is your destination.

This huge outdoor market offers a German Christmas experience in Chicago. Find treasures of all kinds, from handmade ornaments to food vendors, family-friendly events & intercultural activities.

Pro Tip:
Be sure to find the Kinder Club; they offer activities, prizes and entertainment specifically for children. 

Christkindlmarket Chicago Photography by Guy Bauer
Christkindlmarket Chicago – Photography by Guy Bauer

10) Winter WNDRland at the WNDR Museum

Nov 27, 2021 – Jan 2, 2022
1130 W Monroe St, Chicago, IL 60607

The WNDR Museum is a hands-on immersive art experience that is perfect for anyone that loves taking selfies. For the holidays, the museum will totally transform into a Winter WNDRland.

The holiday changes feature a brand new holiday installation, visits from the world’s first LED interactive Saint Nick, an Ugly Sweater Party, a wreath making workshop, WNDRland of the Sweets, and more! Light up your winter in Chicago’s very own WNDRland!

Santa will be at WNDR every Tuesday (4-8 pm) and Saturday (10am-2pm) during Winter WNDRland. He’ll be landing his light-up sleigh and is available for photos on a first come, first served basis. Quantities are limited.

Touchable sequin walls beckon visitors entering the WNDR Museum
Touchable sequin walls beckon visitors entering the WNDR Museum
WNDR Museum in Chicago
The WNDR light floor is made of 100s of motion sensored LED panels
WNDR Museum in Chicago Infinity Mirror Room by Yayoi Kusama
WNDR Museum in Chicago Infinity Mirror Room by Yayoi Kusama

11) Shop the Magnificent Mile

Michigan Avenue, Downtown Chicago

Magnificent Mile shopping, here we come!

Watertower Place is where you’ll find the LEGO store and American Girl Doll store, as well as many brand stores teenagers love.

This is also where you’ll find the storied Starbucks Reserve. Go inside for splendid drinks, cafe items, a bar, and be sure to take the curved escalator all the way to the top.

Pro Tip:
Use Google Maps to plan your shopping strategy in advance and make dinner reservations on Open Table well before your planned dining date.

Chicago Michigan Avenue Magnificent Mile
The Magnificent Mile in Downtown Chicago
starbucks reserve chicago

12) Watch ‘Twas the Night Before by Cirque Du Soleil

Nov 26 – Dec 5, 2021
The Chicago Theatre – 175 N State St, Chicago, IL 60601

‘Twas the Night Before… is a modern spin on the beloved Christmas classic as only Cirque du Soleil could imagine. This festive show about the wonders of sharing and friendship promises to spark lasting memories in the hearts of families this holiday season.

Notes: Video cameras may not be brought into the theater. Children less than 1 year old may attend without the purchase of a ticket.

‘Twas the Night Before by Cirque Du Soleil will play at the Chicago Theatre

13) Ride the CTA Holiday Train

2021 Dates TBA – Check website for updates
Various Locations

Unique to a Chicago Christmas, the Chicago Transit Authority offers the CTA Holiday Train.

Take a ride aboard the city’s elevated train known as the “L” and you may just find Santa or one of his elves handing out candy canes.

Select train cars are also decorated to the max with holiday lights and Santa may even be driving! 

Pro Tip:
Children under 7 ride free with a paying adult on all city trains and buses. If traveling with a stroller, not all city train stations have elevators. Check their website to find station with elevators.

Hoping that Santa will drive our CTA Holiday Train!

14) Older Teens & Adults: Watch Second City Perform “Deck the Hallmark”

November 19-December 31 (No shows December 24-December 25)
UP Comedy Club – 230 W. North Ave, Chicago IL, 60614

Get ready to laugh until it hurts in this Greeting Card Channel Original.

This holiday movie parody “scorches the clichés, tropes, and so-bad-they’re-good romances that have kept cable networks in business and former child stars employed.”

Pro Tip:
– Plan to spend some time in Second City’s neighborhood. Old Town in cool!
– 2 HOUR RUN TIME | 15 MIN INTERMISSION | SEATING 45 MIN PRIOR TO SHOW | Rated PG-13/R, ages 13 and up, primarily for inuendo and language.

Tickets available online
second city chicago hallmark show

15) Take in a Special Event

Various Locations & Dates

Chicago hosts various fun, annual events during the holidays. We recommend scheduling your visit to include at least one of these: 

November 20, 2021: The Magnificent Mile Lights Festival – One million lights illuminated on the trees along The Magnificent Mile! (FREE)
November 25, 2021: Thanksgiving Day Parade (FREE)
December 4, 2021: Christmas Tree Ship

girl smiling on dad's shoulders while watching parade in Chicago
Bundle up for the Thanksgiving Day parade
Family visits Chicago at Christmas

*This article contains affiliate links

More Family-Friendly Things to Do in Chicago

Chicago is a big place, full of family-friendly activities. While these suggestions are not specific to the holiday season, we recommend them as add-ons to your visit anytime during your stay in the windy city:

Sugar Factory – Chicago River North

55 E Grand Avenue Chicago, IL 60611

This restaaurant is in demand and is a lot of fun. TikTok famous for their Smoking Goblet Cocktails (you can get these without alcohol) this place is a sensory delight. Book in advance to secure your time slot.

Sugar Factory Chicago River North has a Restaurant and Sweet Shop

Chicago Architecture River Cruise by Shoreline Sightseeing

401 N Michigan Ave, Chicago, IL 60611

If the weather is decent, this is a fun way to see the city and give your legs a rest.

Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this architecture-focused cruise. View the skyline from the Chicago River while listening to live commentary. Some cruises include a full bar. We did the Shoreline Sightseeing Tour and highly recommend.

Chicago Architecture River Cruise by Shoreline Sightseeing
Chicago Architecture River Cruise by Shoreline Sightseeing

Everything Else – Get a CityPASS

CityPASS tickets are the way to go if you want to see a lot of attractions and save on admission. Available for adults and children. Your pass is valid for 9 consecutive days starting with and including the first day you visit an attraction. You have one year from date of purchase to start using your tickets.

Choose from a 3 attraction pass or a 5 attraction pass.

A C3 CityPass Ticket includes admission to 3 attractions of your choice from this list:
– Shedd Aquarium
– Skydeck Chicago
– Museum of Science and Industry
– Shoreline Sightseeing Architecture River Tour
– Centennial Wheel at Navy Pier

Your CityPASS C5 Ticket includes admission to 5 attractions, including:
– Shedd Aquarium
– Skydeck Chicago
– Field Museum
– Your Choice #1 (Museum of Science and Industry, 360 CHICAGO Observation Deck, or Art Institute of Chicago)
– Your Choice #2 (Museum of Science and Industry, 360 CHICAGO Observation Deck, or Art Institute of Chicago)

*During busy times such as summer, spring break, and holidays, it’s especially important to plan ahead and make any necessary reservations.

The Centennial Wheel at Navy Pier is an option on the C3 Chicago City Pass
The Centennial Wheel at Navy Pier is an option on the C3 Chicago City Pass

Chicago Travel Tips

1) Take the Train to Chicago

If you arrive by train, there is no need to worry about traffic, parking, bathroom breaks or snow covered roads.

Take the Amtrak or South Shore to visit Chicago. You can easily leave from Grand Rapids, Kalamazoo, Lansing, or Michigan City, IN.
Amtrack will deliver you to Union Station in downtown Chicago.

Not only is it stress free – it’s fun!

Amtrack Interactive Planning Map

2) Take a Minute to Learn How to Use the Buses & Trains Offered by CTA

Driving around Chicago and finding a place to park can be a chore – and will get pricey quickly. If you can find a good place to park, leave the car and use the bus or train to get where you need to go.

Google Maps does a great job of helping you find the routes you need to take to get to your destination.

Buy a 1 or 3 day CTA pass and your family will travel easily while you’re in town.

3) Parking Apps are Helpful

Parking apps can help you find open parking spaces and compare the prices of different spots.

You can even reserve a parking spot ahead of time.

If you’re staying in a hotel with a high overnight parking fee, you might be able to find a nearby lot using an app for a fraction of the hotel’s price.

Parking apps that work well in Chicago include SpotHero, ParkWhiz, ParkMobile, and ParkChicago.

Download the app of your choice before your trip, create an account, and input your credit card info to make travel a breeze.

4) Expect Toll Roads

Traveling by car to Chicago usually involves some travel over toll roads.

The Chicago Skyway is a 7.8-mile-long toll road that connects the Indiana Toll Road to the Dan Ryan Expressway on Chicago’s South Side. Currently, it costs $5.80 to drive this stretch of road. You can pay by cash, card or E-ZPass.

This is just one of the Toll roads in the Chicago area.

5) Be Prepared For the Windy City

Chicago has earned its windy city nickname. In November and December, Chicago can be bitterly cold.

Since many of the Christmas activities are outside, you’re going to want to pack warm coats, mittens and hats. If you have younger children in strollers, blankets are a good idea too. 

Despite the potentially chilly temperatures, the stores and street will still be busy. Family events may be busy as well.

We find if we plan for extra time to get places and go into it knowing that there will be crowds, we end up a lot happier.

boys smiling in winter gear on street in Chicago

Where to Stay in Chicago

Check for Vacation Rentals – VRBO or Airbnb

Hotels are everywhere in Chicago, but they’re not always the best option for a family.

Hotel rooms in Chicago’s downtown area are notoriously small. The historic buildings aren’t easily adapted to modern space preferences, leaving travelers to fit into rooms that are likely smaller than desired.

One way around this is to look for a vacation rental that will let you spread out a little bit more. Just be sure to check the ratings and reviews for the listing you’re interested in to make sure it’s in a safe neighborhood and that the hosts are reputable.

The map below shops hotels and vacation rentals in the Magnificent Mile area of Chicago to help get you started.

We’ve also included info on a couple of our favorite Chicago Hotels as well.

Embassy Suites Magnificent Mile: 511 N Columbus Dr, Chicago, IL 60611. A pool, 2-room suites, and a great location just blocks away from Magnificent Mile Shopping and State Street attractions are what drew us to this hotel. That, and the free breakfast and evening reception!

Complimentary Breakfast and Evening Reception is part of the stay

Swissotel Chicago: 323 E Wacker Dr, Chicago Loop, Chicago, IL 60601. Excellent location just north of the Museum District and close to the river. They offer the SWISSOTEL KIDS SUITE, which includes a two-room suite: One room for adults and the signature Swissotel Kids Room. This special package also includes a complimentary in-room movie and breakfast for 2 adults and 2 children.

Swissotel Chicago Kids Suite

Chicago Athletic Association Hotel: 12 S Michigan Ave, Chicago, IL 60603. Located right across the street from Millennium Park, you couldn’t ask for a better location. Plus this hotel has suites that are perfect for families AND Shake Shack is available for in-room dining.

And this hotel has a great backstory, too. This 1893 Venetian Gothic landmark is a living, breathing ode to Chicago’s rich story was a club for the elite that is now open for everyone (the library reminds me of Harry Potter!) Stop in and check out the Game Room and the Drawing Room on the 2nd Floor and then book a room because you’re going to love what you see. Oh, and Cindy’s, their rooftop bar, is one of the tops in the whole city.

Game Room Restaurant at Chicago Athletic Association is packed with shuffleboard, foosball, bocce, billiards, checkers, chess, and more.
chicago athletic association hotel
The Drawing Room (2nd Floor ) offers an afternoon and evening dining menu and is charming beyond measure.

I hope your family falls in love with the magic of a Chicago Christmas the way my family has! 

Are you a Chicago Christmas traveler? Leave us a comment with your favorite activities or tips for visiting!

Holiday Fun Finder

Holiday Menu Button
Holiday Menu Button
Local Gifts Button
Holiday Menu Button
Holiday Menu Button
Holiday Menu Button

More to Explore



Leave a Comment

Your email address will not be published. Required fields are marked *