Love Your Family,  Love Your Travel

Chicago Trip with Toddlers

Vacationing with toddlers isn’t always a happy place. Little ones get tired, but they also like to be busy! Planning trips for them and with them may be difficult. I’ve researched some things that we are planning on taking our 2 and 4 year at the end of this summer to do in Chicago. I didn’t make this trip as packed as a normal trip due to the fact that you never know how your little ones will handle it. I did however add a few extra fun things you could do in addition to the itinerary. As long as you accept and prepare yourself that it will be chaotic at times, you should have a blast! πŸ™‚ That’s my biggest tip for traveling / vacationing with little ones: extra patience goes a long way. πŸ™‚

Day 1

Drive to LEGOLAND Discvoery Center in Schaumberg, IL. (With kids in the city it’s nice to have a car for car seats!) Spend a couple of hours checking things out. They had a 4D show and a bunch of little lego areas to build in. After some play time eat lunch; they have a fun lego lunch box for kids.

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After lunch, drive to Loyola Beach for some fun in the sand. Spend a couple of hours there. Hopefully they aren’t too tired, but my philosophy is it’s vacation! Schedules and naps are going to be crazy! They may sleep in the car on the way to the beach. If they do just let them sleep for a little before, then they’ll be ready to go for some beach fun! Make sure to pack a lot of snacks! If you have toddlers then you know snacking is their favorite thing ever! Also, make sure to pack some beach toys, sunblock, towels, and an easily accessible change of clothes for the drive to the hotel.

Drive to Holiday Inn Express Magnificent Mile and check in. Order Lou Malnati’s Pizzeria once you know your room number and have it delivered! (It’s the river north location on N. Wells St). While waiting on the pizza, this would be a good time to do baths for your little ones. They are bound to be sandy and sweaty! Enjoy dinner in your room, and some cartoons on the tv or IPAD. I also like to make sure and pack their favorite books and a couple puzzles.

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Day 2

Wake up and have breakfast at the hotel. I LOVE hotels that include breakfast when traveling with kids! Let the kiddos play a little in the room with their puzzles while you get ready for the day. Then, drive to Smallcakes: A Cupcake and Creamery. I’d strive to leave by 9:30. It’s only about a 17 minute drive, but parking isn’t always the best. They open right at 10 so that should give you plenty of time with little ones. πŸ™‚ This place is to die for!! Their smashcakes are sooooooo much fun, and kids are bound to love a sweet treat for snack!

This looks so AHHHMAZING! Photo credit:

Drive to Lincoln Park Zoo for the day. Explore the fun andΒ free zoo! You do however have to pay for parking, which is anywhere from $20 – $35 a day. I would definitely suggest bringing a stroller and some snacks for the kiddos. I’d plan about 3 hours for the kids to see the zoo. You could also visit the Lincoln Park Conservatory that’s right next to the zoo if you have time.

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With little ones, dinner is usually around 5. RJ Grunts is literally on the way out of Lincoln Park Zoo. Stop there for dinner. It’s a very kid friendly restaurant!

Head back to the hotel. My kiddos are always exhausted from our long days. Get ready for bed, cuddle, and watch a little tv. Normally we have to lay with ours when we’re all in a hotel room. If you don’t have a separate room, I suggest having your phone readily available. πŸ™‚ Or go to bed early … after all those days also take a lot out of the parents as well!

Day 3

Again, wake up and have breakfast the hotel. Get ready, check out, and head to the Shedd Aquarium. It opens at 9, and I suggest getting there right at 9. Come prepared with snacks and strollers for little ones. Be prepared to pay for parking as well; it’s anywhere from $20 – $25 for 12 hours. Take a few hours to explore. A helpful tip, sign up for the dolphin show when you first arrive. It fills up fast, and you want to make sure you get the time that works for you. I also suggest the sea star touch experience and the polar play zone for little ones.

A cool fish photo I took a few years ago when we went to the Shedd Aquarium.

Leave around lunch time and head to Eleven City Diner for lunch. This place isn’t too far from the Shedd and it so kid friendly! After lunch, head home! The kiddos will hopefully sleep on the car ride home!


Some other fun things to check out if you have time:

Maggie Daley Park– one of the best playgrounds in downtown Chicago! A great place for kids to get their energy out!

Adler Planetarium – near the Shedd Aquarium. Our kiddos love looking at the sky!

Bobby’s Tike Hike Chicago: Kid’s Edition Bike Tour – This would be fun to do! They have all types of bikes for families that would work with little ones. This way parents get to see the sites as well! πŸ™‚

Chicago Children’s Museum – a fun place to explore at Navy Pier.





  • Tabitha Eichelberger

    This article is awesome for me as I am taking the kids in a couple weeks to lego land for Tin’s birthday! Question how much is there really to do at lego land? Would it be an all day experience? Also is the beach close by lego land? Would the small cakes be better to do on the day we do the zoo or is it closer to Schaumburg???

    • Charley

      I would say a couple of hours is all you really need to explore Legoland Discovery Center. I suggest getting there when they open at 10, play for a couple of hours, and then finish with the special Lego Lunch box they offer for kids. The beach is about 40 minutes or so away from Legoland, so not a terrible drive if you want to spend all day away. Smallcakes is about 35 minutes from Legoland and about 20 minutes from Loyola Beach. If you want to spend all day I would suggest Legoland from 10 -12:30ish, the beach from 1:30 – 3 ish, then a stop at Smallcakes on the way home! πŸ™‚ If you don’t want to spend that long in Chicago area, Smallcakes would be perfect when visiting the zoo! πŸ™‚

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