Chicago is one of my favorite cities (next to my beloved NYC, of course) and it’s perfect for a long weekend getaway or a week’s visit for families! There’s so much to do and see in Chicago, especially during the Holiday Season — here’s some excellent ideas of what to do to ensure your family has a great time. Make sure you snag City Pass while you’re there! – quickly go here to get it – Save 51% on Chicago’s 5 best attractions with CityPASS – Shop Now!10 Fun Things To Do With Kids in Chicago During the Holiday Season
Getting from the Airport:
It will take around 50 minutes or so to come in from O’Hare International Airport. Take money for a taxi or Ride on Demand like Lyft or Uber. Keep in mind if you book a Lyft or Uber, they are restricted to where they can pick you up. We came in via United and they picked us up all the way at the front of the United terminals.
Where to Stay:
We love to stay in the city when we visit — one of the hotels I recommend is the Holiday Inn Chicago-Mart Plaza River North. Spacious rooms and located in a very central area. There are loads of restaurants and attractions nearby — or take Chicago Public Transport or Lyft.
Arrive early and stash your luggage at the bellman’s station. Take a photo of your claim ticket (I know I always lose mine). Then go explore!
Apparel Center Drive
Chicago, IL 60654
Terrific Family-Friendly Idea
1. Christ Kindl Market
This is a sampling of what you would see if you were at a German holiday market (which I last saw when I traveled to Munich in Christmastime 1992). There are loads of food stands serving potato pancakes, Bratwurst, hot chocolate, strudel, beer, Bavarian pretzels, specialty candy, German cookies, and many foods dipped in chocolate.
Don’t miss the cheesecake-stuffed Bavarian pretzels! It’s more of a big snack than a lunch or dinner, but it’s a lot of fun. It is outside, so make sure you bundle everyone up! Save room for Hot Chocolate! You can also buy a cute mug for $8 to keep and enjoy your hot chocolate in.
Pick up some great holiday gifts here. Vendors offer jewelry, clothes, home décor, wooden handicrafts, toys for kids, Nutcrackers, cuckoo clocks, and beer steins as well as hand-blown and hand-painted ornaments.
Find the Christ Kindle Market on Daley Plaza in the Chicago Loop (Between Dearborn, Washingtons, and Clark Streets)
SUN – THU 11AM – 8PM
FRI – SAT 11AM – 9PM
2. Get Deep Dish Pizza
Chicago is famous for their Deep Dish. We recommend sharing with friends at Gino’s East. There are several locations and the pizza rocks.
500 North LaSalle Street
Chicago, IL 60601
Have you had Deep Dish Pizza? What’s your favorite place to go to?
3. Have Breakfast at Lou Mitchell’s
Breakfast: Lou Mitchell’s is THE place to go. This diner has been around since 1923 and serves up delicious food.
You’ll meet Donna as you come in. She’s been greeting customers at Lou Mitchell’s for the past 3o years and she’ll great you with a smile and a donut hole.
Don’t miss the banana pancakes!
Or the chicken and waffles (thanks to Greta of Pickles Travel for letting me photograph her breakfast)
After you eat, they’ll give you a small cup of vanilla ice cream and some candy. This is such a family friendly place and I just fell in love.
565 W Jackson Blvd
Chicago, IL 60661
4. See a Sports Team Play
Chicago is full of awesome sports teams. However, tickets can be pricey. Catch a Chicago Wolves Hockey Game in Rosemont, Illinois (around an hour from the city). Take a Lyft out there (they have drop off points right near the area).
Get Tickets for a Game
6920 Mannheim Rd,
Rosemont, IL 60018
5. Visit Chicago’s Museums!
Chicago has many terrific museums for families – make sure you visit the Field Museum. Another terrific museum for families is the Museum of Science and Industry. This is an interactive museum that you could spend the whole day at! Drive or take public transportation here.
While this Museum is on the more expensive side, consider a membership if you plan on coming a couple of times a year. It’s also excellent and kids will love it. You can easily spend a whole day (or more here). 10 Fun Things To Do With Kids in Chicago During the Holiday Season
Make sure you check Groupon – they often have deals for this and other Chicago attractions.
The Museum of Science and Industry
5700 S Lake Shore Dr,
Chicago, IL 60637
Check out my video!
If you plan on visiting several possible attractions, Save 51% on Chicago’s 5 best attractions with CityPASS – Shop Now! — This museum is on it.
6. See The Bean in Millennium Park
Millennium Park is located in the Loop area in Chicago and was intended to celebrate the third millennium. Pop in and take a photo in front of the Bean and then stroll around the park. It hosts the Bean, which is only one amazing piece of the public art available in Chicago – more info here: https://www.cityofchicago.org/city/en/depts/dca/provdrs/public_art_program.html
201 E Randolph St,
Chicago, IL 60602
7. Tour Macy’s and see the Holiday Windows and Dine in the Walnut Room
Check out my video on YouTube: https://youtu.be/-5J8gismAD8
111 N State St,
Chicago, IL 60602
8. Shop the Magnificent Mile
Chicago is known for their excellent shopping. The Magnificient Mile boasts a lot of high-end stores. Plus delicious restaurants to get your strength back like Labriola Cafe.
9. Take in a Show – Chicago has lots of high caliber shows. The Blue Man Group is definitely one of them. It’s family friendly and a quick cab or Lyft ride from the main drag.
Briar Street Theater
3133 N Halsted St,
Chicago, IL 60657
Find more shows at Groupon: https://www.groupon.com
10. Gospel Brunch at the House of Blues
This was so fun! The lively gospel brunch at the House of Blues was so enjoyable and the food was delicious. Get there on the earlier side to grab a seat near the stage.
Gospel Brunch is every Sunday at 10 and 12:30 PM.
Chicago, IL 60654
Find out more about Enjoy Illinois: https://goo.gl/YxHWQc
Get CityPASS –
Get CityPASS — Save 51% on Chicago’s 5 best attractions with CityPASS – Shop Now!
This looks like so much fun! Never been there but will have to start planning for our trip!
Mariah Klee says
This trip looks like such a blast! I haven’t been to Chicago since I was a little girl but it’s only a 4 hour drive from St Louis so it’s on my bucket list to take the kids, especially at Christmas time! Thanks for this article, it definitely added a few items to my itinerary!
Bella B (xoxoBella) says
Chicago is so fun!! The bean was my fav.. I also really enjoyed deep dish pizza! such a fun post.
I have relatives in Chicago and would love to visit one day!
Paula @ I'm Busy Being Awesome says
Chicago during the holidays looks so fun and the food seams delicious!
Is there anything better than going into a disney store over the holidays? Kids (and myself at 23) will love it