Next leg of our 16-day road trip…Chicago!

Where We Stayed

We stayed at the Sheraton Grand Chicago Riverwalk, and it turned out to be the perfect home base. You’re right in the middle of everything, and the views of the river were so pretty—especially at night when all the city lights come on.

Mama Tip: If you can, ask for a room on a higher floor. The view alone is worth it when you’re winding down after a busy day.

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Day One: Riverwalk Wandering and Fireworks

After checking in, we set out to walk the Chicago Riverwalk and stretch our legs after the drive. The kids loved watching all the boats and bridges, and I loved that there were plenty of spots to sit and take it all in.

Dinner was easy and low-key at Island Party Hut, which is such a fun spot if you just want to grab something casual. There were several games to keep the kids entertained while we waited for our food. It felt like the perfect laid-back kickoff to our stay.

After dinner, we caught a view of the fireworks from the Navy Pier right on the Riverwalk. They happen every Wednesday and Saturday night from Memorial Day through Labor Day, and they were such a fun (and free) way to end the day!

Mama Tip: Even in summer, Chicago nights can be breezy by the water—bring a jacket or sweatshirt.

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Day Two: Coffee, Shopping, and Wrigley

The next morning, we started bright and early on Michigan Avenue. First stop: the Starbucks Reserve Roastery. It’s four floors of coffee heaven, and the perfect place to fuel up before tackling a big day in the city.

Next up was the brand new Harry Potter™ Shop, which was a huge hit. Wands, robes, Butterbeer—our little Harry Potter fans were in their element.

Then it was time for a stop my daughter had been counting down the days for: the American Girl Doll Store. Watching her take it all in, pick out a new outfit and accessories for her doll was so sweet— she was in there living her best life.

Not to be left out, our little guy got his turn at the LEGO Store. He would have happily stayed there all day building and checking out all the sets.

After all that shopping, we were ready to eat. We headed over to Lou Malnati’s Pizza(make a reservation before hand) for some classic Chicago deep dish. It did not disappoint. We left absolutely stuffed and in need of a nap.

We headed back to the room for a little downtime before the big event of the day—watching the Cubs play at Wrigley Field. Seeing the kids experience a game there was such a fun moment, and the Cubs won, which made it even better.

Mama Tip: The ice creams come in a little baseball cap, and it makes for a great souvenir for the kids to bring home.

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Departure Day: A Quick Visit to The Bean

The morning we checked out, the weather decided to give us a proper Chicago send-off with a light rain. But we couldn’t leave the city without one last stop.

We loaded up the car and drove over to see The Bean (officially called Cloud Gate). Even in the drizzle, it was so worth it. The kids loved seeing their reflections, and it felt like the perfect way to wrap up our time in Chicago before hitting the road again.

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Ready for more road trip inspiration? Stay tuned for our next post: A Quick Stop at Indiana Dunes National Park: Sand, Sunshine, and a Perfect Break From the Road