2023 Chicago Christmas Trip Planner: Find the Best Holiday Fun in the Windy City

Chicago Christmas Macys

Visiting Chicago for Christmas is a Favorite Family Tradition

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

When the Christmas season rolls around, we upgrade our tradition game and embrace all things merry and jolly. A Chicago Christmas, sometimes getting there by taking the train from Michigan, is hands down my favorite family tradition!

ice rink chicago christmas millennium park
Millennium Park Ice Rink – Chicago at Christmas

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. And the Christkindl Market, yes!

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.

Kids Looking at Skyscrapers during Chicago Christmas

If you’re considering a visit this holiday season, read on for why a Chicago Christmas trip should be on your list:

*this article contains affiliate links

12 Best Chicago Christmas Things to Do & Where to Stay

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 – Shop the Christkindl Market

November 17 – December 24, 2023
Daley Plaza, 50 W Washington St, Chicago, IL 60602

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

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.

chicago christmas christkindl market

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


2 – See the ZooLights at Lincoln Park Zoo

2001 N Clark St, Chicago, IL 60614

ZooLights runs November 17, 2023 – January 7, 2024 this season from 5:30 -11 pm daily. Closed Nov 23, Dec 24 and Dec 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 is back this year with a fresh show and familiar glow featuring 2.5 million LED lights including hundreds of luminous LED displays and seasonal experiences. Soar above the treetops on the 65-foot Ferris wheel for breathtaking views of the skyline and the sparkling lights.

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. Mondays will offer free admission, with reservations still required. Tickets for Monday nights will be available along with all other standard ZooLights dates. Ticket prices range between $7-10.

Lincoln Park Zoo Lights Chicago Christmas

Sensory-Friendly Night is Dec 6, 2023.

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.


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). Skating time reservations required.


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

chicago christmas millennium park ice rink

4 – 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.

Macy's Christmas Window Decorations in Chicago
The sidewalk at Macy’s State Street Location is dressed for the holidays

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


Macy's Holiday Windows
Captivating Window Displays Line the Street

5 – Marvel at Christmas Around The World at the Museum of Science and Industry

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

Holiday exhibit opens November 18, 2023.

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

Chicago Museum of Science and Industry at Christmas
It’s exciting when it snows inside the museum!

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 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
U-505 Submarine – experience a real German submarine, housed indoors.

6 – Get Yourself to the Jack Frost Holiday Pop-up

170 N Green St, Chicago, IL 60642

Billed as “The Biggest Outdoor, Interactive Christmas Event in the Heart of Chicago,” this destination promises to activate all of your senses. This 2-acre experience includes ice skating, holiday pop-up shops, ax throwing, bumper cars, cocktails, photo ops and more.

Open to all ages. Opening Thursday November 30, 2023 in Fulton Market.

Jack Frost Holiday Pop-up Chicago Christmas

Reservations required. Tickets start at $15.

Jack Frost Pop-Up →

7 – Shop the Magnificent Mile

Michigan Avenue, Downtown Chicago

Magnificent Mile shopping, here we come!

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

Chicago Christmas at night

This is also where you’ll find the storied Starbucks Reserve. Go inside for splendid drinks, café 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.

starbucks reserve chicago


8 – Go to a Christmas Show or Holiday Event

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

November 18, 2023: The Magnificent Mile Lights Festival – One million lights illuminated on the trees along The Magnificent Mile! (FREE)

The Magnificent Mile Lights Festival is a favorite Chicago Christmas tradition

November 23, 2023: Thanksgiving Day Parade (FREE)
December 1, 2023: Christmas Tree Ship

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

Chicago Christmas Shows

Nov 4 – Dec 24, 2023: Beatrice Potter Holiday Tea Party (for kids up to age 8)

Dec 2-27, 2023: The Nutcracker at Lyric Opera House

Dec 3, 2023: Mariah Carey – Merry Christmas One And All! at the United Center

Nov 18 – Dec 31, 2023: A Christmas Carol at the Goodman Theatre

Dec 7-28, 2023: Cirque Du Soleil – Twas the Night Before

Dec 19-31, 2023: How the Grinch Stole Christmas Musical

How the Grinch Stole Christmas Musical
How the Grinch Stole Christmas Musical

9 – JoJo’s Winter Wonderland at the 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 area of the patio.

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


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

10 – 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.

chicago christmas walnut room tree
The Walnut Room’s décor and Chicago Christmas Tree are spectacular

Pro Tips:
– Make reservations ahead of time for lunch. The holiday season experience begins November 4, 2023. Tickets are on sale now.
– Lunch is a wonderful experience and a nice way to save on the budget.


Inside Macys on State Street in Chicago
The department store is decked out for Christmas as well

11 – Ride the CTA Holiday Train

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 stations with elevators.


Hoping that Santa will drive our CTA Holiday Train!

12 – Try the Ice Skating Ribbon & Epic Slides at Maggie Daley Park

337 E Randolph St, Chicago, IL 60601

Skating Ribbon opens November 17, 2023, 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.

Ice Skating Ribbon in Maggie Daley Park

Tickets for ice skating go on sale starting November 6, 2023. 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, a suspension bridge, and a multitude 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
Maggie Daley Park at the Slide Crater

More Fun 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:

Color Factory

Interactive journey through 14 immersive art exhibits as stunning as they are colorful. Tickets

Sloomoo Institute

Slime museum experience. Tickets

Museum of Ice Cream

Interactive ice cream experience. Tickets.

Sugar Factory – Chicago River North

55 E Grand Avenue Chicago, IL 60611

This restaurant is in demand and is a lot of fun. Sugar Factory is TikTok famous for its Smoking Goblet Cocktails (you can get these without alcohol). Book in advance to secure your time slot.


Chicago Architecture River Cruise by Shoreline Sightseeing

401 N Michigan Ave, Chicago, IL 60611

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

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 it.


WNDR Museum

1130 W Monroe St, Chicago, IL 60607

Touchable sequin walls beckon visitors entering the WNDR Museum
Touchable sequin walls beckon visitors entering the WNDR Museum
WNDR Museum in Chicago Infinity Mirror Room by Yayoi Kusama
WNDR Museum in Chicago Infinity Mirror Room by Yayoi Kusama

The WNDR Museum is a hands-on immersive art experience that is perfect for anyone that loves taking selfies.


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 the date of purchase to start using your tickets.

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

C3 CityPass Ticket includes admission to 3 attractions of your choice from this list:
– Shedd Aquarium
– Skydeck Chicago
– Art Institute of Chicago
– Museum of Science and Industry
– 360 CHICAGO Observation Deck
– Adler Planetarium
– Shoreline Sightseeing Architecture River Tour
– Centennial Wheel at Navy Pier

Your CityPASS C5 Ticket includes admission to 5 attractions, including:
– Shedd Aquarium
– Skydeck Chicago
Plus get admission to 3 more attractions of your choice. No need to choose now—decide later.
– Field Museum
– Art Institute of Chicago
– Museum of Science and Industry
– 360 CHICAGO Observation Deck
– Adler Planetarium
– Shoreline Sightseeing Architecture River Tour

*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

Getting to Chicago and navigating a big city can be intimidating. Use these travel tips to make your commute a breeze:

Take the Train to Chicago

Amtrack Interactive Planning Map

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 even Michigan City, IN. Amtrak will deliver you to Union Station in downtown Chicago.

Note: The South Shore train is not currently running in Michigan City, IN. If you start your trek here, you will be bussed to Gary, IN and take the train from Gary to Chicago.

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.


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.

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. =You can pay by cash, card or E-ZPass.


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 streets 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.

Where to Stay in Chicago

Try these suggestions for vacation rentals or hotels during your Chicago visit at Christmas:

Hyatt River North

66 W Illinois St, Chicago, IL, 60654

This Hyatt Place Chicago hotel is great, especially if you have a bigger family. You can get a room with two beds and a pull out couch, perfect for a family of 5. Free grab-and-go breakfast included. 8 minute walk to Magnificent Mile.

Embassy Suites Magnificent Mile

511 N Columbus Dr, Chicago, IL 60611

Complimentary Breakfast and Evening Reception is part of the stay

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 made-to-order breakfast and evening reception!

Swissotel Chicago

Swissotel Chicago Kids Suite

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.

Chicago Athletic Association Hotel

12 S Michigan Ave, Chicago, IL 60603

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.

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.

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.

Do you Visit Chicago at Christmastime?

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