For hotels I would suggest either Hampton Inn Chicago Downtown Magnificent Mile or Hampton Inn & Suites Chicago-Downtown. Both Hampton hotels are downtown, however, the first one has an indoor pool while the second one has a rooftop seasonal pool. With older kids, if they like swimming, pools in hotels are always a good bet! Breakfast is also included for families. If pools aren’t necessary I suggest Holiday Inn Express Magnificent Mile.
If you drove into the city or took a train, drop bags off at the front desk of your hotel then Uber or take the CTA Red Line to Wrigley Field. Hotdogs are a must as well as pretzels and ice cream. Nachos are also a nice touch! Depending on how old your kiddos are, they have special games where kids can run the bases on the field. Enjoy a day at the ball park.
Afterwards, head to Chicago Pizza and Oven Grinder in Lincoln Park. This pizza is amazing! If you’d rather not stop somewhere, you can order Lou Malnati’s Pizzeria later and have it delivered to your hotel. Depending on what time you get back, the kids could swim for a bit.
Have breakfast at the hotel. Head to the Disney Store on the Magnificent Mile! After some shopping, head to Sprinkles Cupcakes for a fun and delicious treat! Their cupcakes and ice cream are delicious!!
You can’t go to Chicago without checking out some views! Head to 360 Chicago! If you get the City Pass, you’ll be able to have entry pretty easy. (The City Pass includes quite a bit of Chicago’s attractions. I would definitely check it out to see if it would be worthwhile for you and the family to purchase!) The kids will have fun going on the Skydeck observation; there’s also the TILT ride that they may enjoy.
Next stop is the American Girl Place! Let the kiddos shop, and then have lunch there or have afternoon tea. Make sure to make a reservation. (I can’t wait to take our girls here when they’re old enough!)
*If you have boys, this morning’s activities may not suit them. You could do the sports shops on the Magnificent Mile, but a better idea would be to take them to 360 Chicago, then to Oak Street Beach for a morning of fun. They offer paddle board lessons as well. On the way back to the hotel, you can stop at Sprinkles for a delicious treat. There’s a Portillo’s or a Shake Shack not far from the hotel that would be good for lunch.
After lunch head to Navy Pier for some family fun. They have shops and rides to experience. There is also the Shakespeare Theater that offers family friendly shows. The views of the city are nice, too!
For dinner SafeHouse is a sure bet for some fun! It’s a spy-themed restaurant!! During my research, lots of people have said their cheese curds are amazing so I definitely recommend those!
After breakfast at the hotel and checking out, drive to the Shedd Aquarium. This is one of the biggest attractions for families in Chicago. Be prepared to pay around $25 for parking. When you get there you’ll want to sign up for the Dolphin show or any other shows you want to see. They fill up fast! Have lunch at the café.
Head to the Adler Planetarium to learn all about space. They offer some fun shows for kids. Take a couple of hours to explore.
Go to Eleven City Diner for dinner. They have a fund selection of food for kids! Once full head home!
Some other suggestions that would be good for kids:
Field Museum of Natural History: Learn all about the world’s history.
Museum of Science and Industry: This is one of my husband’s favorite museums. There are some pretty cool exhibits.
Millennium Park: This park has a lot of fun things to see and offers events throughout the year.
Bobby’s Tike Hike Kid’s Edition: Depending on your kids’ ages, this may be perfect for you to check out sights around Chicago!
Lincoln Park Zoo: It’s free and has some great animals!
Garfield Park Conservatory: This place has beautiful and amazing plant life, and it’s open year round! It’s also free!!
Little Goat Diner: This is a great place to eat! It’s on the way to Garfield Park Conservatory, so it’d be perfect to do breakfast there and then head to the conservatory. 🙂
I hope you have some fun ideas for your family!