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Visiting Chicago with Kids in the Winter

Chicago is just about a three hour car ride from our home in Grand Rapids, Michigan. Over the years, our trips to the Windy City have evolved. I used to visit for the weekend and stay with college friends to enjoy big city shopping and late nights out on the town. Later on, I celebrated my bachelorette party and later, our honeymoon there. These days our visits to Chicago look a little different. And we love it! Here’s a recap of our latest whirlwind tour to Chicago, Illinois.

A lovely thing about Chicago is that they are a full hour behind Michigan time. This means we can leave right around 4pm EST and arrive in Chicago just in time for dinner. And because Friday nights are meant for pizza, we LOVED us some traditional Chicago Deep Dish. We highly recommend Lou Malnati’s.

For accommodations, you cannot beat Embassy Suites by Hilton River North. They have a great location, affordable prices, indoor pool, free happy hour beverages and snacks, free breakfast (with a lovely made to order omelette station) and we very much enjoy having a full suite where the kids get their own space in the living room pull out couch. It also comes with a mini fridge and a coffee maker.

On our latest trip we took the full morning on Saturday to explore the Museum of Science and Industry. It was incredible and I cannot say enough good things about our visit there. There is so much stuff for the kids to see/do and is fully interactive. We pre purchased our tickets online for a 9a entry and stayed until Noon. A couple pro tips, there is free parking along S. Stony Ave (at least on the weekends) otherwise you can pay $30 to use the ramp under the park in front of the building. You also should take some time to plan out your visit once inside. Most of the bigger exhibits are timed entry and they fill up fast! So grab a map and scope out your route and make your reservations first thing. We were bummed to miss out on the tour inside of the submarine but thoroughly enjoyed the Maze of Mirror and the Blue Paradox.

Whenever in town, we almost always grab a meal at Beatrix. They have a fabulous brunch/lunch menu as well as an awesome dinner menu. They also offer a fabulous (always bustling) atmosphere, great cocktails and a kids menu. The River North location just just blocks away from the hotel.

After lunch on Saturday we made the 1.3 mile walk (pro tip: we always bring the kids scooters when visiting) from Beatrix to Willis Tower to check out the SkyDeck and man o’ man was is cool. I did underestimate the time it would take to fully get through the experience. Upon entry you spend the first 30 mins weaving through a storytelling exhibit about the the city of Chicago - everything from notable people who are from there to the city’s history and more relevant things like how the building was constructed. Once we finally reached the top of the 108 floors (there were lots of ushers and different elevators on the way up) we were left breathless by the view. It was the clearest of days and no joke we could see our great state of Michigan on the other side of the lake.

By the time we finally got through our SkyDeck experience we were ready for a quick break and headed back to the hotel. The kids were eager to swim in the pool and I had stashed a bottle of wine in our room to enjoy poolside while they exhausted what seemed like boundless energy. Plenty of time for a quick shower before happy hour at the hotel and then off to dinner.

For dinner Saturday night we went big with reservations at Cindy’s on the Rooftop at the Chicago Athletic Club. The menu is stellar and we thoroughly enjoyed our tomahawk steak for two and were delighted when the server offered the kids a menu of their own including a cheeseburger and fries (something they did not advertise on their website). Ambiance was lovely and they had fire pits going on the outdoor patio overlooking Millennium Park. Be sure to make reservations!

After dinner we walked to Millennium Park where they have two seasonal options for ice skating. The first is just near the iconic Bean sculpture and is your basic ice rink where you can rent skates and get cocoa. The second option is just a bit further of a walk into Maggie Dailey Park - the chidlren’s portion of the park - where you will find the ice skating ribbon. We brought our own skates and saved some dollars and booked our entry ahead of time online (good for two hours of skate time). We had a fabulous time skating the path meandering the park there.

Visiting Chicago with kids in the Summer? Read about our 2022 visit HERE, summarized list below:

  • The Shedd Aquarium is a great option for your Saturday morning or on Sunday on your way out of town.

  • The Lincoln Park Zoo has free entry and free street parking (on the weekends) surrounding the park. On Saturdays (in the summertime) there is also a great farmers market in the park adjacent to the zoo that’s perfect for grabbing lunch at before or after your visit.

  • Water Tower Place - Here you will find The American Girl Doll Store as well as The Lego Store. Bring your credit card!

  • Navy Pier at night is lovely and the perfect time to ride the Ferris Wheel.

  • Maggie Dailey Park might be the coolest playground the kids have ever visited. Grab a cup of coffee and take a walk through Millennium Park (make a stop at the Bean sculpture) and let the kids run around before you head out of town.

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