I always love spending time in Chicago and showing my kids the amazing city we have in our backyard. We had a fabulous family staycation at the Four Seasons downtown over winter break. We did 3 full days and 2 nights of fun! Here’s our itinerary and some other fun city ideas to explore!
Day 1: Our first stop was at Camp – part store, part immersive experience with new activations every quarter. Currently it’s the colorful world of Doodles. Upon entry, we created a doodle character and started a scavenger hunt to collect stuff for our character along the way of playing. The rainbow playground was filled with slides, a ball pit, games & more. I recommend buying tickets for this in advanced. You can also add a craft pass to do additional activities. The next activation is Bluey in May and my kids are already asking if we can go.
My kids requested pancakes for lunch, so we headed over to Kanela Breakfast Club. Other options I love near Camp for breakfast/lunch are Small Cheval, Foxtrot, Nookies and Happy Camper. My dinner recs in the Old Town neighborhood are Twin Anchors or Topo Gigio.
Next we checked into the beautifully, newly renovated Four Seasons. The location was perfect all of the exploring we wanted to do and there is no better service than the FS. Upon check-in we immediately went to the pool which is incredible. Swimming was followed by early bird special dinner at one of our favorite old haunts, Luxbar. Kevin and I slurped down cocktails as our children were mildly behaved. Luxbar has chicken nuggets & fries on their bar menu which is all my kids need.
Day 2: Breakfast was a trip to Stan’s Donuts and Ralph’s Coffee, both are walking distance from the hotel. Since we are at the mercy of a baby’s nap schedule, my big kids had a morning swim while baby snoozed.
We headed to Navy Pier for the Chicago Children’s Museum. If you are a kohl children’s museum member you receive half off your ticket price. Navy Pier has a large food court located right next to the museum with McDonald’s, Potbelly, Big Bowl & many other options – something for everyone! We had a quick lunch before heading to the museum. My kids (ages 3 & 6) both loved the many interactive exhibits at the museum.
We had dinner across the street from the hotel at Doc B’s and then visited the Sprinkles Cupcake ATM for a treat!
Other restaurants nearby I love: RL, The Lunchroom, Lou Malanti’s, Gibsons, Maple & Ash, Blue Door Kitchen & Garden, Adalina and The Pancake House.
Day 3: Started with a sweet trip to the Museum of Ice Cream. Located in the Tribune Tower and it will stay as fixture for the foreseeable future. The museum was a colorful curation of immersive installations of childhood fun! There were fun photo opps, tidbits on the history of ice cream and games. The sprinkle pool at the end was a highlight for my kids. You are able to indulge in unlimited ice cream flavors including hot dog flavored ice cream served in a pink bun. The whole experience was about 1-1.5 hours long.
We of course had to have one last swim at the pool. The Four Seasons Chicago pool is where the pool scene in Home Alone 2 was filmed. My kids are obsessed with that movie and referring to it as “Kevin’s Pool”
On the way back home we stopped by one of our favorite city spots, Roots Pizza. Roots gives out pizza dough for the little ones to play with while waiting on your food. We noshed on their collaboration pizza with Monteverde and it was *chef’s kiss* delish!
Other Chicago favorite things to do with kids are: Museum of Science and Industry, Shedd Aquarium, Sloomoo Institute & Lincoln Park Zoo.
*Parking tip: we found overnight parking nearby on SpotHero instead of valeting our car at the hotel. Always an option worth exploring when you’re traveling!*
