Chicago is a great destination to travel to with kids as it offers a wide variety of family-friendly attractions and great pizza restaurants to visit. There are are many fun things to do in Chicago in the Winter with kids, from watching a show at America’s first-planetarium to having fun with the hands-on exhibits at the Museum of Science and Industry.

A few days before our trip I was searching Skyscanner for where I could take the kids in January. I try to make sure to take the kids someplace new every month, so I was excited when I saw $20 one-way tickets on Frontier Airlines to Chicago. I quickly bought our tickets and then searched for things to do in Chicago in the winter with kids.

PS: Did you know that Kids Fly Free on Frontier Airlines starting February 2019?

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We spent 5 nights total in Chicago and had such an awesome time. Some of the top things to do in Chicago in the winter with kids are listed below.

Chicago In The Winter With Kids

Best Time to Travel to Chicago With Kids

The best time to visit Chicago is between April to May or September to October as the temperatures are warm and the crowds are manageable. Summer is the peak season in Chicago with lots of festivals and outdoor activities. This means that there will be a lot of tourists and the city will be busy. Airfare and hotels rates are also much higher during the summer. If you want to visit Chicago on a budget, the best time to do so is from November to March, but expect freezing temperatures, especially in January.

We visited Chicago in January and the temperature ranged from 20F to -20F. It was very cold and snowy; however, we packed layers and didn’t have any issues with the cold.

How To Travel To Chicago In The Winter With Kids

There are many ways to get to Chicago depending on where you are leaving from. We flew from Palm Springs airport to Chicago on a direct flight. I always pack food before our trip so the kids can have something good to eat, this time “jollof rice“. I also take an empty water bottle to fill up at the airport filling water stations. As you know, buying anything at the airport costs way too much!

Packing For Chicago In The Winter With Kids

I packed light smart because Frontier Airlines charges a fee for luggage, both carry on and checked-in luggage. I really wanted to keep my $20 flight tickets at $20 by spending no more than that. So, I packed our clothes in packing cubes and then packed the packing cubes in our backpacks. The kids and I both use Osprey backpacks. Another tip for packing light is to pack bar soap instead of liquid soap, and shop the dollar section at Walmart or Target for travel essentials.

Transportation Options in Chicago In The Winter With Kids

• Taxi: Taxis are a convenient and fast way to get around the city but it can be quite pricey as the fare rate depends on the number of passengers and the gas prices.
• Lyft/Uber: Lyft and Uber both operate in Chicago in the winter and are much more affordable than taxis. All you need is to just download the app and book a ride.
• Rental Car: Getting around with a rental car is quite easy but it is quite difficult to secure a parking spot downtown. There are parking garages that you can park the cars but the hourly and nightly rates are quite expensive.
• Public Transportation: The cheapest and fast way to go around the city is through the buses and trains of the Chicago Transit Authority (CTA). The trains are popularly called L and they may be elevated or underground.
• Hop On/Hop Off Bus: The Hop On/Hop Off bus in Chicago is a perfect way to see the city. You can purchase a pass for a day which stops at most major attractions allowing you to explore the city at your own pace. Do note that this isn’t the best option in

We have been to Chicago twice; the first time I rented a car because I had to drive all over, however this time we did not. If you plan to stay downtown and do activities downtown, then public transportation is your best option. Parking fees are as high as $40 a night so keep that in mind if you really want to rent a car.

On this trip we used public transportation as well as Uber and Lyft when it was to cold to wait outside for the bus or walk to the train station. If it was summer, we could have easily made it through out trip by using public transportation only. The train station was just a few minutes’ walk from the airport terminal, and I purchased a 3-day Ventra/CTA card. When our 3 days was up, I added money to the our Ventra card so we could continue to ride the bus and train.

Where to Stay In Chicago In The Winter With Kids

Traveling with kids can be hectic and a right hotel can go a long way to help reduce stress. There are many hotels in Chicago with lots of amenities which will help to keep your kids entertained while some offer discounts to local museums. Some of the best hotels in Chicago are listed below.

• Four Seasons Hotel – This luxury hotel is close to the Magnificent Mile with lots of family-friendly amenities and activities. Teens can enjoy activities like pizza making class or specialized treatments at the spas. The hotel also has storytellers that you can hire to read bedtime tales to your young ones. The hotel also has a child pool that your kids will love.
• Fairmont Chicago – This hotel is located in downtown Chicago and it is close to Millennium Park. The hotel provides many family-friendly activities like the Shedd Aquarium package and picnic totes and park package where you can enjoy a gourmet picnic in Millennium Park. The hotel also has separate rooms for kids and parents with babysitting services. There is also the kids’ menu at the hotel restaurant.
• Swissotel Chicago – This is a stunning hotel which also features a Kids Suites and Very Important kid check-in that has an area for reading, coloring, and playing. The kid suites are separate but adjoining to the main room and it houses child-sized furniture and amenities like video games, stuffed animals, and DVDs that your kids can play with.
• Best Western Plus River North – This is a perfect family-friendly hotel for you if you are in Chicago on budget and it is located in the heart of downtown Chicago. The hotel is close to many attractions that you can easily walk to and it also features a full-size indoor pool that your kids will love.
• Raddison Blu Aqua Hotel Chicago – This is a magnificent hotel that is located close to the major landmarks in the city and it features a rooftop swimming pool that both parents and kids will love. The hotel also provides many family-friendly amenities and activities that you will really enjoy from the weekend afternoon tea service to kids camping package.

Where Did We Stay In Chicago In The Winter

• Hampton Inn Chicago Downtown – we stayed at this hotel on our first night and I booked it using Hilton points so it was a free night. This hotel is located right downtown and walking distance from the train station as well as several attractions.
• Chicago Getaway Hostel – we spent 5 nights in this hostel. Most people don’t realize this but there are many kid friendly hostels. We also recently stayed at a kid friendly hostel in Copenhagen last year which the kids loved. I booked the private with shared bath on Hotels.com because of their free night program (collect a free night after 10 stays) and on Booking because I found the cheapest price for the private room there.
  • Private Room with Shared Bath ($32/N) – I was curious about what it was staying in one of these rooms with kids so I booked it for two nights. There was a bathroom down the hallway and the boys and I showered there in the morning. The room had a bunk bed, a sink and a toilet. The prices on HotelsCombined, Hotels.com and TripAdvisor where the same for this room, but I booked it on Hotel.com because of their free night program (collect a free night after 10 stays)
  • Private Room and En Suite Bath ($52/N) – This room is huge and can perfectly sleep up to 8 people. So, if you travel to Chicago with a large family and want to save money, this is perfect. It has a microwave, fridge and private bathroom in the room. I booked it on Hotels.com because it has the cheapest prices.

When searching for hotels, make sure to check at least 3 to 4 different websites. When booking accommodation, TripAdvisor is the way to go because you can read reviews and see photos from other travelers to get a feel of where you will be staying. Other great sites to book hotels are HotelsCombined, Booking.com and Hotels.com. Don’t forget to check HomeAway and VRBO for house and villa rentals too. Perfect for when you travel with a large family, and also to save money when hotels are expensive. Another favorite of mine is BookVIP – they offer huge resort savings.

Top Things to Do In Chicago In The Winter With Kids

If you plan to stay downtown Chicago and want to visit the top tourists’ attractions there, then make sure to get a City Pass. This will give you access to visit 5 of the top attractions in Chicago in the winter which are listed below.

Things To Do In Chicago With Kids Covered By The City Pass

1. Shedd Aquarium: This stunning attraction homes more than 1500 species of marine and land creatures like snakes, birds, fish, insects, and amphibians that you can see. The highlight of the aquarium is seeing exhibits like the Amazon Rising which displays caimans, anacondas, etc. and the Wild Reef where you will see rays, numerous species of fish, and sharks.
2. Skydeck Chicago: this offers amazing views of Chicago from way up high. Make sure to check the visibility before you go. The weather wasn’t good when we went so we weren’t able to see anything.
3. Field Museum: this is a natural history museum that offers lots of learning opportunities for both adults and kids. My favorite part of the museum was Africa and the kids loved the animals and dinosaur movie. 
4. Choose Adler Planetarium or Art Institute of Chicago
   • Adler Planetarium: this attraction offers immersive and hands-on exhibition for your kids. This is also a perfect place to take family pictures.
   • Art Institute of Chicago: this is one of the oldest museums in the United States and also one of the best art museums to visit in Chicago.
5. Chose Museum of Science and Industry or 360 Chicago Observation Deck
   • 360 Chicago Observation Deck: this is similar to Skydeck Chicago; however it offers 360 views of Chicago from up high. Make sure to go on a day with great weather.
   • Museum of Science and Industry: this museum is huge and there is so much to do and see here. The kids loved playing and learning here. Plan to spend the whole day.

Other Things To Do In Chicago In The Winter With Kids

Because Chicago can get very cold and snowy in the winter time, indoor activities are very much recommended.

• Play With Snow: it snows in Chicago and it snows a lot. So if your kids are curious about experiencing snow, then Chicago in the winter with kids is a great idea.

A post shared by The Akpan’s | Family Travel (@themomtrotter) on Jan 23, 2019 at 4:29pm PST

• Chicago Children’s Museum: this is a first-rate museum which provides lots of play and learning opportunity for your kids with many engaging attractions to keep your kids busy.
• Emerald City Theater: this theater has lots of kid and family-friendly plays to enjoy.
• Skating Ribbon: fun thing to do if you are in Chicago in the winter. You can also enjoy magnificent views of downtown Chicago while skating. It is free to skate if you take your skates, if not that’s okay, you can pay a fee to rent a pair of skates.

• LEGOLAND® Discovery Center: ultimate family destination with lots of exciting and interactive exhibits that your kids will love. Keep in mind that this place is about 40m away from Chicago.
• DuSable Museum of African-American History: this museum was founded in 1961 by Dr Burroughs and features African-American art and culture.
• Escape Game Chicago: This is a fun indoor activity that you can try out while in Chicago in the Winter with kids. It is an indoor game where you will be locked in a room and given 60 minutes to figure out how to get out of the room with a lot of clues and game master ready to help you if you are stuck.
• Millennium Park: this is a huge park compromised of The Bean, Maggie Daley Park and Crown Fountain.
  • Maggie Daley Park: awesome kids park which feature’s Chicago’s only outdoor climbing park.
  • The Bean: if you don’t make it to the bean, then maybe you didn’t really visit Chicago. This is located in Millennium Park and a huge tourist attraction in Chicago.

Things To Do In Chicago With Kids Year Round

• Centennial Ferris Wheel at Navy Pier: This ferry wheel can be found in Navy pier and it is a thrilling way to get magnificent views of Chicago and the lakefront.
• Lincoln Park Zoo & Rides: Popular attraction in Chicago for families with lots of animals to see and thrilling rides to enjoy.
• Millennium Park
  • Crown Fountain: water fountain that kids can run around and play in the summer.
• The 606 Trail: this is a popular park with a bike track and pedestrian pathway which runs along Bloomingdale Avenue.
• Chicago River-walk
• Chicago Botanic Garden
• Chicago Shakespeare Theater

Best Chicago Museums For Kids

• Kohl Children’s Museum
• Illinois Holocaust Museum & Education Center
• Peggy Notebaert Nature Museum
• DuSable Museum of African-American History
• National Museum of Mexican Art
• Museum Of Science and Industry, Chicago
• Chicago Children’s Museum

Best Chicago Parks and Playgrounds for Kids

• Maggie Daley Park
• Lincoln Park
• Grant Park
• The 606
• Oz Park
• Millennium Monument
• Milton Lee Olive Park
• Ping Tom Memorial Park
• Millennium Park

Chicago In The Winter With Kids Itinerary

We spent 5 days total in Chicago, and this is what we did on each day. I did researched and grouped each activity close by each other in order to avoid spending a lot of time going from one end of the city to the next. In the summer time the Hop On/Hop Off Bus is perfect for this. We ate breakfast at our hostel, packed a good snack and then went out to dinner each night.

• Day 1: Millenium Park, The Bean, Maggie Daley Park, Crown Fountain (Free)
• Day 2: DuSable Museum of African American History, Museum of Science & Industry (Free & City Pass)
• Day 3: Navy Pier, Ferris Wheel, Chicago Children’s Museum
• Day 4: Field Museum, Adler Planetarium, Shedd Aquarium (City Pass)
• Day 5: Skydeck Chicago (City Pass)

Where to Eat in Chicago With Kids

There are so many yummy restaurants in Chicago. The one thing I did know for sure is that I had to try Chicago Deep Dish Pizza. The kids and I were excited to try it and we enjoyed it. We tried Lou Malnati’s Giordano’s and Pete’s Pizza and Pete’s was definitely our favorite. Because it was very cold, the kids insisted on having spicy Thai soup, so we ate at JJ Street Thai food almost every night we were in Chicago.

Pizza

• Lou Malnati’s
• Pete’s Pizza
• Gino’s East
• Giordano’s
• Uno’s Pizza
• Home Runn Inn Pizzeria

A post shared by The Akpan’s | Family Travel (@themomtrotter) on Jan 26, 2019 at 4:45pm PST

Other Places To Eat In Chicago With Kids

• • Smoque BBQ
  • Wildberry Pancakes and Café
  • Nookies
  • Eleven City Diner
  • The Polo Inn Bridgeport U.S.A.
  • Yolk – South Loop
  • Do-Rite Donuts & Coffee
  • Original Pancake House
  • West Egg Café
  • The Chicago Diner
  • Harold’s Chicken
  • JJ Street Thai Food

A post shared by Aiden A. | Travel + Food (@boomgoestheboss) on Jan 25, 2019 at 5:24pm PST

Best Tips for Visiting Chicago In The Winter With Kids

• Take Note of A Few Terms – There are some terms that you will hear frequently while in Chicago and you should try to get familiar with them. The downtown central business district of Chicago is known as the Loop while there is a river which borders the north and west. Another term is the L and it means the train.
• Pick up a Ventra Card – This is a convenient way to pay for the CTA system and this will give you the chance to pay for train and bus ticket online without having to queue at machines.
• Check the Weather – Chicago experiences a six-month winter with short summer and it is best to check the weather forecast before you leave the house. This is because the weather changes throughout the day and you don’t want to be caught off-guard with downpour or drop in temperature while exploring the city.

Chicago In The Winter With Kids Budget

• Flights: Frontier $60 (3 one way tickets from ORD to PSP) / United (I had a United gift card which I used for this trip from PSP to ORD)
• CTA Ventra Card: 5 days $30
• Hotel: Chicago Getaway Hostel $220
• Meals: $200 (I packed lots of snacks, bread, croissant, cookies etc. The hostel offered a light breakfast so we ate only one meal out each day). Or else we would have easily spent a lot more.
• Uber/Lyft: $200 (This was much more than I hoped to spend, however, it was so cold that we needed to use it. If I had rented a car it would have cost me a lot more for the car rental and parking fees)
• City Pass: Kids (3-11) $89 and Adults (12+) $109. We received 2 complimentary tickets. 1 additional ticket was provided by the boys homeschool. I love the fact that the boys homeschool charter offer opportunities like these for them when they travel.
• Chicago Children’s Museum: $14.95 for children and adults. We received 3 complimentary tickets. If you have a membership at your hometown children’s museum you may be able to get in for half of or even free. The boys homeschool would have also covered entry for us if we needed it.
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• Total: $710 for 5 days and 5 nights in Chicago in the winter with kids

Thanks to City Pass for providing 2 complimentary passes and Thanks to the Chicago Children’s Museum for providing us complimentary passes. As always, all opinions expressed are my own.