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Weekend trip to Chicago with kids

Chicago is known for a lot of things – deep dish pizza, Chicago-style hot dogs, Polish sausage (now the secret is out – you know I always think of food first, lol), the Sears Tower, Al Capone and of course, its nickname as the windy city. With a repertoire like that, I’m not sure why it’s taken us so long to visit. Well, we tagged along on Clint’s work trip to check out this great city. It was a short visit but one that has wet our whistle to go back again. There is so much to see and do in this amazing city.

Evelyn and Ainsley on a Big Bus Tour, Chicago
Enjoying a snack on our Big Bus Tour

We had Friday to ourselves since Clint had to go into the office. To help us get the lay of the land we started our day off by taking a Big Bus Tour. These bus tours are a great way to see the city and also allow you to hop on and hop off to see the sites closer. I have to admit it’s also a great way to get around town as well. The girls were quite eager to see everything. Every time we learned of another site the girls said: “we need to go there”. I told them “it’s on the list”. Unfortunately, we didn’t get to cross all the items off. Therefore, we’ll just need to go back. Yeah!

Museum of Science + Industry

We stopped and checked out the Museum of Science + Industry. This was a very large museum with many different exhibits from transportation, to trains, to a submarine, to space, to weather, to a fairy castle. In other words, there is something for everyone. The girls and I had a fun time exploring the different exhibits. Above all, both girls enjoyed the space exhibit. Here they are dressed up as an astronaut.

Evelyn as an astronaut, Chicago Museum of Science + Industry.
Evelyn as an astronaut
Ainsley as an astronaut, Chicago Museum of Science + Industry.
Ainsley as an astronaut

Personally, I loved the weather exhibit. There are so many fascinating aspects that cause our weather to be what it is that seeing it in action is remarkable. I could stay and watch the different experiments all day long.

planes at the Chicago Museum of Science + Industry.
The planes were cool as well
City Parks

We also discovered the parks of Chicago. Chicago’s main large park is made up of more than one park, several really. Millennium park which has the Jay Pritzker Pavilion, Harris Theater Millennium Park, Cloud Gate, the Crown Fountain, and Lurie Garden within it. Then you have Maggie Daley Park which has a whole host of activities. For instance, there are slides, swings, spray parks, climbing structures, and enchanted forests to discover. There is also Butler field, Grant Park, Grant Bark Park, The Green at Grant Park and Hutchinson field. In addition, there are fields and monuments and fountains to wander around. This large central park is an oasis in the city. A gathering place for people to have fun and be outside enjoying each other and nature.

Millennium Park, Chicago
Jay Pritzker Pavilion. There wasn’t a concert when we visited but I’m sure it is a special place to see a concert.

We also found a geocache while visiting this park. Just be careful there are many muggles around. My kids pretended they were looking for a missing earring and it worked. They were able to find the cache and no one was the wiser. Such fun.

Cloud Gate, Chicago
I love the reflection of the city skyline in the Gate Cloud

Gate Cloud

The Gate Cloud is a popular photo opp. If you don’t want to be overcrowded, go early in the morning or on a workday, for instance. We took Clint on a Saturday morning after breakfast and there were just too many people there to even see yourself in the reflection. In other words, you want the space to be empty so you get a great photo of yourself in the Gate Cloud.

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Crown Fountain, Chicago
Crown Fountain

Crown Fountain

A much-welcomed attraction on a hot summer day. The crown fountain goes through a cycle of peoples faces on the bricks and when the water sprays out it looks like it’s coming from the person’s mouth. The girls got a kick out of it. Evelyn is in the blue with her back to the camera and Ainsley in is the yellow shorts. We went back in the evening and there were lots more families playing in the water.

Crown fountain in action
Millennium Park, Chicago
Flowers in full bloom

I love when there are flower gardens within a large city park. It brings wildlife, color, a lovely fragrance and a human scale to the park.

Maggie Delay Park, Chicago
The playground is spectacular
Maggie Delay Park, Chicago
What child wouldn’t want to try going through a castle like this?
Maggie Delay Park, Chicago
The Enchanted Forest
Maggie Delay Park, Chicago
Little kids spray park
Maggie Delay Park, Chicago
Climbing wall. The girls are on the left

Chicago River Cruise

The next day was a little overcast so we decided to take a cruise down the Chicago River. We learned all about the architecture and history of the city. This was one of my favorite activities. I do still love learning and seeing the architecture of different places we travel to. Chicago is no different. The great fire of 1871 burned for more than 24 hours right through the heart of Chicago, killing 300 people and leaving one-third of the cities population homeless. Of course, Chicago rebuilt and as time past the architecture of the city changed as well, giving you the diverse and modern city you see today.

Marina Towers, Chicago
The ‘Corn Cob’ buildings, some of my favorites.
Chicago Tribune Building, Chicago
The Chicago Tribune
End of the river tour, Chicago
The skyline from the river cruise

Navy Pier

Another fun place to visit in Chicago is The Navy Pier. There is an amusement park. However, there are also shows and entertainment, cruises and site seeing, dining and shopping and the children’s museum. In other words, there really is something for everyone. We took advantage of the clearing weather and went on the Centennial Wheel and a few other attractions. If you like these activities you should also check out the Killington Adventure Center in Vermont.

Navy Pier, Chicago
The Navy Pier from our hotel room
Centennial Wheel, Chicago
Centennial Wheel
View from Centennial Wheel, Chicago
Evelyn looking down from inside Centennial Wheel
View from the Centennial Wheel, Chicago
The skyline from inside Centennial Wheel
Merry-go-round, Navy Pier, Chicago
Merry-go-rounds are awesome too!
Climbing Wall, Chicago
Evelyn trying to make it to the top
Climbing Wall, Chicago
Ainsley almost at the top

We were grateful to the balloon man for providing a bit of entertainment while we waiting for our dinner at Jimmy Buffett’s Margaritaville restaurant.

Balloon art, Navy Pier, Chicago

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Do-Rite Donuts, Chicago

Gluten-Free Donuts at Do-Rite Donuts

We couldn’t leave Chicago without trying the famous Do-Rite Donuts! Evelyn was thrilled to have 3 choices. Of course, we had to buy some for the trip home. Hey, you never know if you will find what you want to eat at the airport. She was covered for her dessert at least. Ainsley loved the donuts as well. Vowing to make sure we come back, if not for the love of Chicago then for the donuts she’d like to have more of.

Do-Rite Donuts, Chicago
3 choices of gluten-free donuts!

Have you been to Chicago? What is your favorite part of the city? What is your favorite food?

This Post Has 54 Comments


    It looks like a great time! Love the fountain and donuts!

    1. Leeanne

      Yes, it was a great trip. We would love to go back for longer than a weekend.

  2. Jennifer

    Looks like you had lots of fun adventures. The Crown Fountain is amusing. Love to get some closeups of the pink flowers.

    1. Leeanne

      It was a really fun weekend. I good taste of the city that has us wanting more.

  3. Missy

    Yes, I would go through a castle like that. Okay, I am hungry for a hot dog now.

    1. Leeanne

      It’s funny how certain street food is the best in different cities. These were good hotdogs.

    1. Leeanne

      Absolutely the best. Now I want to go back and spend another week there to do even more.

  4. jen

    I used to drive by that fountain all the time. I always thought it was odd LOL but it didn’t stop the kids from wanting to play in it.

    1. Leeanne

      It wouldn’t stop me from playing in it either.

  5. Yuri Barber

    Beautiful photos. Windy City is on my bucket list

    1. Leeanne

      Chicago really is a great city. I’m sure you will enjoy your visit.

  6. Wow, that playground is spectacular! And my kids would love the rock climbing! But that fountain though….. I think it would creep me out, lol. Thanks for sharing your adventures.

    1. Leeanne

      The playground is really cool. The Crown Fountain really is great. I promise you, in person it’s awesome.

  7. Chantelle

    So much great information! Tucking this away for our trip later this year!

    1. Leeanne

      I’m sure you will love Chicago when you get there. It’s so rich with history and culture and food!

  8. Cindy

    I have been to Chicago on an adult trip and saw very different things. I loved seeing your perspective of visiting with children.

    1. Leeanne

      Yes, well, I would love to go back to Chicago on a long adult-only weekend myself but that’s a bit tough for us since we don’t have much family around.

  9. Amy

    Those fountains crack me up every time I see them!

    1. Leeanne

      The Crown Fountains are awesome. The faces change and it’s so cool to have the water spraying out of the people’s mouths.

  10. Jordin

    I LOVE Chicago! Next time I go I will need to check out the river cruise.

    1. Leeanne

      Definitely check out the river cruise it is so great.

  11. Jordan

    I’ve been to Chicago once and was sad to run out of time for the river cruise. I definitely want to visit again and do this. Also, I love donuts, so am adding Do-Rite to my list!

    1. Leeanne

      You definitely want to try Do-Rite donuts. We loved the river cruise too, even on a slightly rainy day, it was still amazing. Architecture was my first love so it’s no wonder I loved the river cruise.

  12. Tricia Snow

    Gluten-free donuts! YES PLEASE!

    1. Leeanne

      Are you gluten-free? Our older daughter has celiac disease so we are always on the lookout for good gluten-free restaurants and bakeries.

  13. Lisa Manderino

    We love Chicago. I was about to book tickets this week for a summer trip but my mother in law found out she has cancer. So we may not get to go now, we don’t want to visit grandma if she is doing cancer treatments 🙁

    1. Leeanne

      I’m so sorry to hear about your mother-in-law Lisa. I hope she gets through the treatments fast.

  14. kmf

    Love Chicago and have visited several times since it’s so close, but I have never seen that fountain (so cool) and would love to take the Chicago boat tour. Chicago has some great architecture and history.

    1. Leeanne

      Chicago does have amazing architecture and history. I would love to take the Untouchables tour, I’m just not sure it’s kid-friendly enough for my sensitive girl. But it’s part of American history that I love reading and learning about.

  15. Shirley

    Donuts? You had me at donuts! When my young granddaughter gets a bit older, I would love to take her to Chicago for a weekend. Thanks for the tips!

    1. Leeanne

      There are such wonderful places to visit in Chicago for kids. I’m sure your granddaughter will love it.

  16. Taci- Life Beyond Zebra

    Chicago looks so fun! Looks like a great weekend, I would love to visit one day.

    1. Leeanne

      There is certainly something for everyone in Chicago.

  17. Cynthia

    So fun! I would love to take this trip with my kids as well. You posted a lot of great activities. I’m going to post for later!

    1. Leeanne

      Chicago definitely has a lot of kid-friendly activities. I’m sure they will love it.

  18. Stacey Billingsley

    We loved our Chicago visit, and I’d go back anytime. I loved the Museum of Science and Industry. The parks are great, too. I need to take my youngest; she hasn’t been yet.

    1. Leeanne

      Sounds like you need to visit Chicago again. We’d love to go back too.

  19. heather jandrue

    We love Chicago. It is such a great city, with so much to do. Plus, we have family there, so it makes it extra special.

    1. Leeanne

      That’s double-dipping which makes it even more fun since you can have adventures together.

  20. Courtney

    Looks like a fun trip! We have not taken our girls to Chicago yet!

    1. Leeanne

      There is so much to see and do I’m sure you can find lots that they will love.

  21. Julie Gazdecki

    We love Navy Pier!! I need to visit the donut shop next time I’m there!!

    1. Leeanne

      We love the Navy Pier too. Do-Rite donuts are awesome! I’m sure you will love them.

  22. Amanda

    My mom’s family lives right outside of Chicago. I need to get back there soon. This list of things to do with kids in Chicago is great. Looks like you made some wonderful memories!

    1. Leeanne

      Yes, we did make great memories and the girls definitely want to go back.

  23. Tanya

    Give me alllllll the food!

    1. Leeanne

      I’m with you. It’s funny how some destinations we become more food-driven than others but Chicago is certainly one place you need to go around and try all the wonderful food the city has to offer.

  24. Adrian

    Soo many cool kid-friendly activities.

    1. Leeanne

      Yes, there really are a lot of kid-friendly activities which makes it all the better to visit Barbados.

  25. Beth Shields

    Chicago is like a favorite city for me to explore. I used to live close by and would head into the city just to see the sites and the museums. There is soooo much to do that I always enjoyed going there. Your pics brought back memories of those times. Thanks for your post – very informative for things to do.

    1. Leeanne

      Thanks, Beth. I always love it when I read about other people enjoying cities and places that I love as well.

  26. Holly Bird

    Chicago is one of my favorite cities and so much fun for the whole family! Great pictures!

    1. Leeanne

      Chicago is a great city for sure. I’d love to be there for St. Patrick’s Day when their river is green and celebrate with them.

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