Personal Memories: A Weekend in Chicago With the Fam

December 3, 2023

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Early last month we went to Chicago for a weekend with the kids and my mom. I had been meaning to take them to Chicago for forever now, but it kept getting pushed back. We lucked out with fantastic weather and the kids were extremely happy and excited the whole trip, which made for amazing memories.

Key Stops:

Morton Arboretum – We stopped here on the way in and let the kids run around. It’s such a cool spot we will probably be making some day trips here in the future.

The Shedd Aquarium – This is what I had been wanting to bring the kids to for forever. It was busy, but the kids had a lot of fun.

Navy Pier – We ate a Chicago dog here, but we didn’t go up in the ferris wheel – we’ll have to come back.

Lincoln Park Zoo – We stopped at Lincoln Park Zoo on our way out of town, but they weren’t open yet. The kids still got to see a zebra and the walk was nice.

The Skydeck at Willis Tower – This is something I thought I had never done (my mom reminded me on the way up that in fact I had done it and then it came back to me that I did do this as a child) but it was fun to experience again anyways. There were some lines though, so I’m not sure I would recommend it for kids – they thought parts of it were cool, but overall it was a bit boring for them.

Other Places on our List for Future Trips:

Lakefront Trail

The Field Museum

The Adler Planetarium

Maggie Daley Park

The Museum of Ice Cream

Legoland Discovery Center


We didn’t go to many restaurants this trip due to the one and three-year-old, but here are some places I had on my list of options that were safe with kids:

Little Goat – We didn’t end up going here but I’ve heard awesome things and definitely want to try it on a future trip.

Old Irving Brewing Co. – Same with this one.

Ed Debevic’s – This place holds a lot of childhood memories for me as it was the go-to restaurant for us whenever we would come to Chicago. My other childhood restaurant memory is a thing of the past… rest in peace Rainforest Cafe.

Superdawg Drive-In – This looked super fun and Augie would have loved it (he’s my hotdog kid).

The Original Pancake House – We’ve stayed at the Thompson across the street from this a few times and always eat here for breakfast when we do.

Stan’s Donuts – We did end up eating breakfast here before we left, as it was right across the street from our hotel.

Giordano’s – My kids looooooove pizza so this was an easy option right by our hotel. We got it to go and let the kids eat it in our hotel room.

Where to Stay:

For this trip with kids I knew I wanted a hotel with a pool to entertain them and for the location to be somewhere a bit closer to the river (I usually prefer to stay closer to Lincoln Park where it’s quieter, but most of things we would be doing were south of the river).

Park Hyatt – This is where we stayed and the location was perfect. More perfect, however, was the fact that they had a pool – which was one of my prerequisites for this trip with the kids. Swimming in the hotel pool may have been their favorite part of the whole trip.

Getting Around:

Walking – Our hotel location was great and we were able to walk to eat and walked most of the way down Michigan Avenue to the Shedd.

Driving – We drove and parked at Lincoln Park Zoo because we left pretty early in the morning and parking wasn’t an issue. Parking at the hotel was expensive, but convenient.

Uber – We took an Uber most places and it was pretty easy. I did bring our Doona and our Wayb Pico in case they ended up requiring us to have the kids in carseats, but they didn’t so we just hopped in and out without them.

Water Taxi – We took the water taxi from the Shedd to Navy Pier and the boys LOVED it. We actually bought the ticket for a taxi that goes all the way to Michigan Avenue so we were able to get off at Navy Pier, eat a hotdog, and then get on another boat that took us up the river to Michigan Avenue.

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