A closer flight than Hawaii but a further one than Los Angeles, Chicago is a family-friendly destination from Seattle (about a 4 hour plane ride away) that I didn’t really think about when the kids were small and I kind of wish I had. It’s really easy to get around and it’s such a clean and history-filled city. I’ve been spending more time there in the past couple years because of my husband’s work and it’s a fun place to tag along. It’s harder for our teenagers to travel lately-so maybe a reminder to get in as much as you can while they are little-we have group projects now at school, bigger exams, sports and all things teenage life. We still appreciate any flight that is non-stop from seattle (I have a list of them) as it allows us to make the most of the limited time we have together these days.

What makes Chicago a family-friendly destination?

Chicago is really walkable and there are lots of things to see for both kids and grownups. I recently stayed at the Loews hotel and we had a suite with a fridge in the room. The fridge made snacks and breakfast foods really convenient. This hotel was really convenient to Target, Whole Foods and a Paris Baguette (none of these are that many steps away). I could load up the fridge with bubbly water, yogurt, berries and cup up vegetables etc. and this made healthy snacking a whole lot easier. The Loews hotel also has a big pool that is very shallow that would be great for kids too. So many things I wanted to see were only a short walk away.

But if I could stay anywhere in Chicago so far it is the Intercontinental, because the pool at the Intercontinental Chicago is still the most spectacular pool I’ve ever seen. I think they have movies on certain nights in the pool as well if you’re into that kind of thing too. A cool historical fact about this hotel is that it has a roof that was made for zeppelins to dock to but none ever ended up docking there. (This building was also made in 1929 and I guess it’s coming up on its 100th anniversary soon)

There are lots of activities within walking distance of many of the city center hotels

You don’t really need a car if you’re downtown Chicago. Many of the places are walkable or a short taxi ride away (often about 10 dollars which is somewhat the same as parking for a short time in Seattle). There is an elevated train that is an adventure in itself. And one of the most popular attractions, an architecture cruise takes you on a bit of a travel adventure but you don’t have to go very far to get to it. I tried the Divvy Bikes to do the Lakefront trail (not a kid-friendly thing but I think there are places you can rent bikes for families too). I had trouble figuring out the locations of some of the parking docks for the Divvy Bikes. I don’t know if I would bike in the actual city like I do in Seattle-cars seem to drive pretty aggressively and even as a pedestrian I felt like I needed to be a bit more alert.

Here are some of the activities we have enjoyed in Chicago so far

The Skydeck in the Willis Tower: this is an activity we try to do every time we’re in Chicago and it used to be called the Sears Tower so you might know it as that building. It’s not just a building with views, there is a bit of a preamble that you walk through on the way to the elevator where you see so many of the city’s highlights. (This is where we first thought about going to Second City comedy shows and without kids, this is one thing I know we’ll do often in the city. The shows are hilarious and we just saw “This too Shall Slap” that runs through Oct 2025 so far and we laughed so hard.) Pay attention in the elevator at the Skyjack and you’ll see how Chicago gets shaped over the years after the Great Fire of 1871 to how it looks in our present day. The “Ledge” is a must do and I’m scared of heights too but if you just close your eyes as you walk out you don’t have to look down. (I still did and it still scared me but maybe I’ll get desensitized over time).

The Chicago Art Institute: This gorgeous art museum is another place I will want to visit again and again. I like to see A Sunday on La Grande Jatte — 1884 and Nighthawks and I actually stumbled on a tour while I was waiting for the space in front of Seurat’s painting to clear out and listened in for a few minutes and I think I’ll do an art tour next visit. I have done a few tours in the city and my favorite so far was one of the Rookery with the Frank Lloyd Wright Foundation. There is a special exhibition right now until mid-July 2025 “Frida Kahlo’s month in Paris a Friendship with Mary Reynolds” and it was a $5 additional fee to enter this exhibit on top of my Chicago C3 by CityPASS.

Architectural Boat Tour: I could probably do an architectural boat tour every time we visit Chicago too and there are a few different companies that run these tours. If you have a Chicago C3 by CityPASS or a Chicago CityPASS it’s a really easy thing to go to the first three places I’ve mentioned here and save a lot of money because the Shoreline Sightseeing Architectural boat tour is also now one of the options on the pass. And this is what I planned to do on my most recent trip- I’d been generously been given a Chicago C3 by CityPASS again (I’ve used it multiple times in the city and gifted it to my parents on a trip too) and had visited the SkyDeck and the Art Institute. But I had discovered DivvyBikes and riding along the lakefront trail and we had gone on a Hornblower dinner cruise on the water so I thought I’d try a new thing for my 3rd activity and bike to the Shedd Aquarium. This Aquarium is great for kids and grownups but they are doing a major renovation that will done in 2027 and it’s still open and I think you’ll still see a lot. But because I rode a Divvy Bike I got myself completely lost trying to find out where to park my bike with the construction in front and I ran out of time. I found the Divvy Bike system more complex than other bike systems I’ve used so I just recommend giving yourself more time and energy than you think you’ll need when you use these bikes.

Lincoln Park Zoo-if I hadn’t walked through the entrance myself I wouldn’t have believed you if you told me this zoo was free (my friend Dana told me and this is why I rented a bike and zoomed all the way from my hotel to see it). It is spacious and gorgeous and it was filled with school trips the day I went and I bet it has them all the time and it’s the kind of place that makes you feel good about the world. It was really cool to see kids excited about animals and I think we need places like this to teach our next generations about how to be good stewards of our planet. I got here after I walked the Magnificent Mile, had a latte at Ralph’s Coffee and then walked to Oak Street Beach and rented a bike near there to get to the zoo. I got lost trying to find out where to dock my bike at Navy Pier near the Loews hotel. Getting lost with Divvy bikes was a bit of the adventure theme of my last Chicago trip but also they gave me such a different perspective of the city and I don’t regret it at all.

Lip Lab: I love seeing how things are made and this is where you can make your own lipstick, lip balm and lip gloss. Lip Lab is all ages apparently according to its website, just under 18’s need to be accompanied by a parent. Lip Lab is from Toronto Canada and it is pretty wonderful to have your own lipstick shade blended right in front of you in the way Coldstone Creamery makes its ice cream. You can choose the case it comes in and have the name you create laser engraved on the case. I love the colors that I got and I love the way the lip balm and lipstick feel on my lips. I customized the flavor too. There was a coupon online when I booked so make sure you check for that when you make an appointment. Lip Lab in Chicago was walkable to Girl and the Goat and I had a 7pm Lip Lab appointment and was able to make our 8pm dinner reservation.

A few Chicago cafes I like to visit (ones I’ve visited on multiple trips, and I’ll update this more.)

Goddess and the Baker: I love their breakfast burritos, their fancy coffees, their salads, their decor and everything about this place. The name is perfect.

Doughnut Vault: this one has a really cool front door that you might just walk by. Their doughnut holes are big enough to be almost regular doughnuts.

Eataly: yes, this place is a chain but we don’t have one in Seattle and this one has been walkable from every hotel I’ve stayed at so far.

(I’m going to keep this post as a working list and update it over time. Chicago is a place I’ll be visiting at least yearly now and I love that Chicago is a family-friendly destination from Seattle too. Do you have any favorite places to visit in Chicago?)

Terumi

Terumi Pong is a Seattle-based family travel writer and mom of twin teenage boys.  She loves coffee and pastries, shopping local and looking for greener ways to live.  She is also known as Scout’s mom (Scout is a 5ish pound little black yorkie-poo)