4 Days of Family Fun in Chicago

Advisor - Diana Morales
Curated By

Diana Morales

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  • Chicago

  • Family Travel

  • Luxury Travel

  • City Travel

  • Kid-Friendly

  • Summer

  • Outdoors

Chicago river framed by tall buildings.
Curator’s statement

I like to describe Chicago as a giant playground. One where everyone can have fun. It does not matter who you are or what you're into, I guarantee you that there is something for you to explore or to fall in love with. This is particularly true when it comes to families that are traveling with kids. Chicago is full of family-friendly activities! If you want to take your kids to a destination where they will never get bored, look no further than the Windy City!

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Where to stay

Four Seasons Hotel Chicago

Best-of-the-best on the Magnificent Mile, with standout service and unmatched views of Lake Michigan and the cityscape.

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  • Breakfast daily

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theWit Chicago, a Hilton Hotel

Fun-loving Chicago Loop hotel with stunning city views from the bedrooms and rooftop, and nightly DJ sets in the popular Tavern bar.

Swissotel Chicago

Comfortable contemporary hotel with traditional travel style rooms and an indoor swimming pool.

Advisor - Diana Morales

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Day 1: Get a Lay of the Ground

Aerial view over a green park in Chicago.

After you land at O'Hare airport, head to your hotel. I highly recommend staying in the downtown area, you will be really close to all of the activities on this itinerary and you'll have easy access to the city's public trains and buses. I highly recommend that you stay at either the Four Seasons in the Magnificent Mile, Hilton Chicago in the Loop or Swissôtel Chicago. All of these hotels have excellent for kiddos and know how to take care of families.

After you have settled in your hotel, it is time to begin exploring! Whether you only have half a day or a full day to explore, you'll definitely want to start by heading over to Millennium Park and Maggie Daley Park. The order in which you do these does not really matter, they are right next to each other, so you could do one and not the other or do both, it does not really matter. But keep in mind that it is a huge area, which means lots of walking! So if you have toddlers, I recommend bringing a stroller. At Millennium Park, you will find the iconic Cloud Gate, A.K.A The Bean! You can take fun and silly family photos as you see your faces reflected on this structure. You will also find a splash park — so bring your swimsuits! There are tons of gardens for everyone to enjoy, and free entertainment as well. Once you're done there you can head over to Maggie Daley, where you will find mini golf, a climbing wall, and playgrounds all over! This is a great place for families that are traveling with older and younger kids! If you decide to do Maggie Daley first and Millennium Park second, you can delight yourselves with a delicious deep-dish pizza at Giordano's, there's one right next to the park. It does not get more Chicago than that! Of course, you'll need dessert afterward, so stop by the Nutella Café that's down the street from Cloud Gate! The whole family can enjoy a Nutella-inspired treat! After this, you'll be ready to enjoy a nice relaxing night at your hotel.

Day 2: Chicago's Museum Campus

Museum in Chicago.

For your second day, head over to Chicago's Museum Campus. Here you will find three incredible sites for families: The Field Museum, The Shedd Aquarium and The Museum of Science and Industry. The Field Museum is Chicago's most well-known museum. It is full of history and world-class exhibits. If you're traveling with older kids who love history, an exhibit like the Ancient Americas or Evolving Planet could be very interesting for them! If you're going with younger kids, explore the Underground Adventure with them. They will have a blast pretending that they are an insect and discovering the underground world. If you want something more interactive, or if your kids are very interested in science and engineering, then The Museum of Science and Industry is the perfect choice. Every single one of their exhibits is incredibly interactive and suitable for children of all ages. They'll have a chance to learn about storms, trains, farming, DNA, and so much more! Of course, animal lovers can not miss out on The Shedd Aquarium. You and your kids will be able to visit dolphins, penguins, sea otters, sharks, turtles, fish, and even beluga whales! You can do any of these as either a full-day or a half-day activity. If you choose to do a full day, all of these sites have cafeteria areas where you can enjoy a nice meal or sit down for a quick snack.

Day 3: Beach Day

Lincoln Park Zoo with a lion statue in Chicago.

After all of those activities, you'll need a day to relax a bit, so head to the beach! There are so many options to choose from, but I promise you can't go wrong! If you want to fit in some adventuring, you can walk through the amazing Lincoln Park Zoo before settling at North Avenue Beach. If you want a smaller but lively beach, head over to Montrose Beach instead. But if you really want some peace and quiet, Ohio State Beach, 12th Street Beach, and 31st Street Beach are all great choices for that. After a day of family fun in the sun, I'm sure you'll be hungry, so for dinner, you might be interested in something very typical of the city. You can find a place for Italian beef or grab some Chicago-style hot dogs by the beach! Or find a Portillo's nearby!

Day 4: The Sears Tower

The Sears Tower overlooking Chicago.

On your fourth and final day in the city, you can say goodbye to Chicago by going to the Skydeck on The Sears Tower (it's called Willis Tower now, but since I'm a Chicago native, I can't bring myself to call it that!) Enjoy majestic 360 views of the city. If you're brave, stand on the glass deck and take some photos! Once you're done there, head over to Navy Pier, where you'll be able to go into Chicago's Children's Museum if you want to. The museum is definitely for younger kids, this is not a place for teens or tweens, but there are plenty of activities for them also! They can go for a ride on Centennial Wheel, or enjoy the other attractions right next to it. They can also do some shopping if they're into fashion. The whole family can go for a walk along the pier, and enjoy lunch or dinner at the many restaurants in the area. While you're there, make sure you stop by and get a bag (or several!) of Garrett's Chicago-style popcorn. If your kids are into ice cream, stop by The Original Rainbow Cone, another Chicago staple! After all of that, you will definitely be ready to say goodbye to the iconic Windy City, one of the most dynamic cities in the world!

Advisor - Diana Morales

Travel Advisor

Diana Morales

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This guide is part of our ongoing series on travel to Chicago.