Traveling to Chicago with a Baby and Toddler

After a couple of years of not getting to travel, we wanted to spend a couple of weeks in a new, fun and more importantly family-friendly destination. With finding a fun place to travel with toddlers in the USA in mind, we finally decided on a Chicago family trip.

Chicago is located on Lake Michigan shore and despite being one of the biggest cities in the US, Chicago is less visited than other cities in the US, such as New York. In addition, Chicago has plenty of beautiful parks, incredible architecture, and history. It seemed like there would be no shortage of things to do in Chicago with toddlers.  

Aside from all the Chicago toddler activities we discovered the city had to offer, we also appreciated the time zone. Coming from Chile, we only had one short stopover in New York and not dealing with toddler jet lag would mean a more rested trip for everyone.

Of course, we know that traveling with a baby or toddler isn’t synonymous with a relaxed trip, but we were really shocked by how disconnected we were able to be. This allowed us to relax and enjoy visiting Chicago with a toddler and baby.

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When to Visit Chicago with a Toddler and Baby

We traveled to Chicago in spring, with a 1 year old and a 3 year old. We chose to visit Chicago in Spring because this time of the year the temperatures in Chicago are warm, making it easy to walk around and sightsee.

On cooler days, we needed a light jacket, but we only had a few windy and cold days. We were easily able to find indoor activities in Chicago for toddlers, like museums or conservatories. The rest of the time we enjoyed sunny and warm days.

Getting to Chicago

We traveled by plane from Santiago to New York, then on to Chicago. We chose an overnight flight, so the kids would sleep. When flying with a toddler, we use a JetKids Bed box by Stokke.

This airplane toddler bed transforms his seat into a tiny bed, making his sleeping much more comfortable. We appreciate that it folds up into a suitcase, making it easy to transport our toddler around the airport. He loves it and so do we!

Read our full review of the JetKids BedBox by Stokke here.

Besides using it as a airplane bed and for getting a toddler around the airport, we can pack books, coloring pencils, and a couple of toys as his toddler airplane activities.

Our youngest slept in my arms, so she could rest and breastfeed comfortably. Needless to say, my husband and I didn’t get our beauty rest, but that’s pretty common when flying with a baby plus we were happy knowing that the kids would wake up somewhat rested. That, and our morning coffee kept us going.

Where to Stay in Chicago with a Baby or Toddler

We stayed at the Cambria Hotel, located on Randolph Street, in the heart of the Theater District.

We chose this hotel for our Chicago trip with a baby and toddler for many reasons:

1. The rooms were large, so in the case of staying in because of the baby we would be comfortable enough. We had a mini bar in our room, where we stored the baby food we brought from Chile, a microwave, and a kettle.

2. The Cambria Hotel is walking distance from Grant Park, one of the biggest green areas of the city, formed by Millennium Park, Maggie Daley Park, Buckingham Fountain, Art Institute of Chicago, and the Museum Campus. Visiting these Chicago parks would always be an easy option to entertain our toddler if we had had any spare time.

3. There are all kinds of services nearby, such as restaurants, pharmacies, and shops, without being a loud area. One block away there is a Macy’s department store, and in front of the hotel there is a shopping center with cafes and different kinds of stores.

4. The Cambria Hotel is located walking distance from the riverwalk, a fun area full of restaurants and bars, and with beautiful sights of the city.

While the hotel has a restaurant, it did not offer breakfast. We never ended up eating at it because at lunch time we were usually out, and dinner time was too late for our kids. Even when traveling, our baby and toddler usually have an early dinner and go to sleep very early.

Eating out in Chicago with Babies or Toddlers

For breakfast we would usually go to a café, as there were a great variety of them close to our hotel. Some mornings we would eat something in our room before leaving. We would order in through the Cornershop app or Uber eats, some basics such as fruits, cereal bars or different types of nuts.

A portable high chair for travel, specifically a fabric highchair, is easy to carry and use in hotel rooms for babies and toddlers!

We went to Wildberry’s on a few occasions, because it was within walking distance, it would open from very early in the morning, was family friendly and had plenty of good options.  We always had good service, the food was good, and it was a great place to eat with a toddler and baby. They had highchairs available and there was a changing table in the women’s bathroom. And the biggest benefit: it is in front of Grant Park, specifically Maggie Daley Park.

For the rest of our meals, we would eat in restaurants or cafeterias, or would order in through delivery apps. This last choice was the safest one if we wanted a healthier meal for the kids.

For feeding our baby while traveling, we packed baby food from Chile to last several days. We would ask for it to be heated in restaurants if we were eating out.

When we tried to buy baby food, we had to do it in a supermarket or through the delivery apps. Near our hotel we had a Walgreens, which didn’t have a very large selection of baby food.

For snacks, we would always carry fresh fruit, fruit purée, nuts and water in our backpack diaper bag.

For our toddler, every restaurant we visited was kid friendly, with different options for them on the menu, most of them had highchairs and my kids were offered crayons and drawings to color while waiting for the food in almost every restaurant. Not all of them had changing tables in the bathrooms, but that’s not a problem if you are carrying a portable diaper change pad.

Getting Around Chicago with Toddlers or a Baby

Getting around Chicago with a toddler and baby, we decided to mostly walk. Our hotel location was so good that it was easy to get to different attractions by walking.

Our oldest would usually walk, and our baby would be in the travel baby carrier, not only to move from one place to another, but also to take her naps there.

In retrospect, a toddler travel stroller would have been useful! There were times when our oldest would get tired after walking too much. A stroller would have been an easy way to get around. We had made the decision to travel as light as possible, so we made do.

If the distance was too long, then we would use a taxi, or an Uber.

Read more on Uber with a baby

What to Pack for Chicago with a Baby or Toddler

Our baby carrier is a must-have baby travel essential! The one we use is the ErgoBaby 360 air mesh, and we absolutely love it! It makes transportation easier and faster, is small enough to store it in our backpack. We’ve also used it frequently to get our baby to sleep on vacation.

A compact travel stroller would have been useful on this trip, but we frequently travel very light, so we were used to managing with our baby carrier. We could also have used a toddler travel carrier for those times when our oldest needed a break from walking.

Diapers, formula, baby food and other baby products (such as sunscreen or even snacks) we took with us from Chile. We didn’t have to waste time getting these things and it gave us a lot of extra space on our way back home.

But if we hadn’t done this, it would have been extremely easy to get them in Chicago, not only from the variety of stores located near our hotel, but also using any delivery app.

Here is a quick list of the travel essentials we recommend:

• Baby formula. Don’t risk not finding your specific brand at your destination. For instance, the one we use (Töpfer) is not sold in the US. We learned this the hard way, once we were on vacation in NY, and finally had to use a different one, not knowing if the baby would accept it or have a special reaction to it (luckily, it wasn’t the case!)
• A baby carrier, I am in love with our ergobaby, and highly recommend it.
• A lightweight umbrella stroller or a toddler travel carrier.
• A light jacket that can easily fit in your backpack not taking a lot of space, especially for chilly, windy days.
• Sun hat
• Sunscreen
• Comfortable shoes

We have a complete packing list for travel with a baby or toddler, but if you are looking to pack light, renting baby equipment while traveling is an excellent way to do that.

Look into renting baby gear in Chicago.

Best Things to do in Chicago with a Baby or Toddler

We visited Chicago with a baby and toddler for fourteen days. When we started to look at what to do in Chicago with a toddler and baby, we knew that two weeks was probably not necessary, but we wanted to be able to travel slowly, get to know the city’s rhythm, and have the time to repeat any attraction if we felt like it.

We didn’t want to be in a hurry, especially knowing traveling with a baby and a toddler could be unpredictably and oftentimes plans change.

We didn’t have a fully planned Chicago itinerary, but we had a general idea of the places we wanted to visit. We tried to visit one or two Chicago attractions per day, which gave us plenty of time to get from one place to another.

Here are the main attractions we enjoyed with toddlers on our Chicago family trip:

1. Shedd Aquarium

Shedd Aquarium is one of the best Chicago toddler activities. The different exhibits could have you walking around a whole day. There are different options for eating and having a delicious meal.

2. Field Museum

Located on Grant Park is the Field Museum, a natural history museum with several exhibitions. For anyone visiting Chicago with toddlers, the most interesting ones will likely be the ones related to animals and dinosaurs, as they were for our little ones.

It’s a big museum, with exhibits for every taste. We had lunch in the cafeteria, which offered a number of options, all of them child friendly. We got to the museum early in the morning and left after lunch, but you could easily spend the whole day walking through hallways filled with history and interesting facts.

3. Navy Pier

Navy Pier has many attractions, especially if you are traveling to Chicago with toddlers or kids. There are plenty of restaurants, shops, a carousel, or even a boat ride through Michigan Lake.

We visited the Children’s Museum, an interactive museum for children of all ages. Our oldest had a blast, he could easily play all the games. Our baby had fun, but she has fun everywhere, especially if she is with her brother.

We also got on the Centennial Wheel, from which we could admire the city from a different perspective. And in Giordanos, a restaurant located at the entrance of the pier, we finally tried the famous Chicago Deep Dish Pizza. Delicious!

4. Museum of Contemporary Art

Unlike other museums, this is a rather small one, which made it easier to visit without that feeling of missing out on the rest of the exhibitions. My husband and I took turns visiting the various exhibitions, the children would go with us or be in the museum’s garden.

We had lunch at Marisol, a restaurant inside the museum, which didn’t have a kid’s menu but had interesting choices for them that worked very well. In front of the museum there is a playground, where the kids could play and have a snack before continuing our stroll to the Magnificent Mile.

5. The Magnificent Mile

The Magnificent Mile is the name of the commercial district of Chicago, filled with shops, tulips and, as the rest of this beautiful city, historic buildings everywhere you look.

We walked through the area and stopped at the Reserve Roastery Starbucks, the biggest Starbucks in the world. We had some coffee and pastries, and rested for a little while, looking out at the big avenue at our feet.

We dismissed the idea of shopping with the kids, it’s so boring for them that it becomes very difficult for us. If this is something you came to Chicago for, then this is definitely the place!

6. Millennium Park & The Bean

Millennium Park, a five-minute walk from our hotel, is a beautiful attraction, with gardens, old trees, tulips and the huge sculpture that lures many tourists: Cloud Gate, popularly known as The Bean.

We recommend that you visit this spot early in the morning, because it gets very crowded later in the day. In this green area complex we spent a lot of time, enjoying the views and the colors of the spring scene. There are public bathrooms, which are always handy, especially traveling with a baby.

7. Art Institute of Chicago

Art Institute of Chicago is a beautiful art center, with an incredible collection of modern and contemporary art. To see its many exhibitions, my husband and I again took turns. One of us would be with the kids, who at one point just wanted to play on the stairs.

Even though a visit to the museum may not be very interesting for toddlers, I still highly recommend it. I am a true believer that early exposure to art is always a gift for your soul, and they will always remember at least one painting or sculpture that will mean something to them.

8. Maggie Daley Park

This is by far one of the most entertaining things to do in Chicago with toddlers. A group of different playgrounds, for all ages up to 12 years old, can offer you hours of fun and games for the youngest, and a little rest for us, the parents.

Besides being very amusing, it is also beautifully designed. Climbing, sliding and swinging are only some of the things kids can try here. Outside of these playgrounds there is a minigolf, which you must pay in order to play. It’s small and not very beautiful, but our oldest enjoyed it.

9. Lincoln Park Conservatory

We visited the Lincoln Park Conservatory and the Peggy Notebaert Museum. The Lincoln Park Conservatory is a huge greenhouse where you can see and enjoy different species of plants. The Peggy Notebaert Museum is an interactive nature and science museum for children of all ages – one of Chicago’s toddler activities to add to your list.

Our children especially enjoyed the exhibitions involving real animals and insects. They loved the lab exhibition, where they could see different reptiles and amphibians. They also loved the Butterfly Garden, where they would walk among different types of butterflies.

The Conservatory and the Museum are separated by a ten-minute walk, as is the North Pond Restaurant, located by the big pond of Lincoln Park. We visited this place for Mother’s Day and had a delicious brunch, with plenty of child-friendly options.

10. Garfield Park Conservatory

We also visited the Garfield Park Conservatory, where we strolled through the Conservatory. Being one of the oldest greenhouses in Chicago, it was beautiful and very large. This was a wonderful thing to do in Chicago with a baby and a toddler.

11. Chicago River Architecture Tour

One of our favorite activities was a boat tour on the river. We took the Chicago River 90-minute Architecture Tour, which allowed us to learn about the city and its different buildings and architecture styles, listening to a very funny tour guide. If you are looking for toddler activities in Chicago, our kids loved the experience of riding a boat.

Especially for those on a Chicago trip with a baby, having the option to sit under a cover or in the sun was really nice. We really appreciated being able to sit in the shade, because it was a hot, sunny day. This was more comfortable for the kids. While we lost some of the sights the added comfort was more important for keeping everyone happy during our trip to Chicago with toddlers!

12. Lincoln Park Zoo

There is a zoo at Lincoln Park, and it is one of the oldest in the US. We didn’t visit, but apparently it has beautiful exhibitions and a great variety of animal species.

13. Chicago Nightlife

While more difficult for parents on a Chicago trip with a baby or toddler, Chicago has many attractions that take place during the night, such as restaurants, bars, and theater. The riverwalk is supposed to be a great place for this! Unfortunately, we didn’t experience it, but if you are able to manage a babysitter it could be great fun!

Final Thoughts on a Chicago Trip with a Baby and Toddler

Deciding on which Chicago attractions you want to visit depends 100% on the taste and interests of each family. For us it was very important to be outside, in parks and playgrounds. We also wanted to take our kids to different art exhibitions and museums, considering that they had missed out on these cultural experiences the past two years.

We were able to stroll unhurried, which allowed us to enjoy every moment and make beautiful family memories. We fell in love with Chicago and would visit it again in a heartbeat!

We hope our experience traveling with a toddler and a baby to Chicago inspires your next journey!

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