Our Girls Weekend in Chicago

If you don’t already know, I’m the youngest of 4 girls – no brothers! This is the point where most people say, “Oh, your poor dad!” but don’t feel bad for him. He has 2 son-in-laws and 6 grandsons. But before those 6 grandsons came 3 granddaughters. That’s right. 7 girls in a row for our family!

For the past 3 years in November, all 8 of us girls (my mom, my 3 sisters, my 3 nieces, and me) have went out of town on a Girls Weekend. Each year we go somewhere new. Always within driving distance, usually somewhere with an American Girl Store. 😉 This year we chose Chicago and spent 3 days seeing all the classic sights, shopping, and exploring the city!
Highlight Video
Why We Chose Chicago
The kiddos had their sights set on Chicago for months before we actually went, for one reason only: the American Girl Place. Us adults didn’t turn it down for a lot of reasons. Being from St. Louis, Chicago is a pretty easy drive for us and we knew there would be tons of things to do in Chicago that would be kid friendly.

Where We Stayed
I’m a big AirBNB gal and any time I’m the one in charge of booking, I always choose an AirBNB, BUT for the kiddos, having a hotel with a pool is half the fun of traveling. So for this trip, we opted to go for a hotel on the Magnificent Mile. The great thing about staying here, was that we were within walking distance for almost everything we wanted to do — I think we only took an Uber once.
What We Saw
Obviously, the very first thing the girls wanted to see in Chicago, was the American Girl Place, but before we could head there, we needed to eat! Of course, Chicago style pizza was on the list of things to do while being there and Gino’s East was close to the hotel, had great ratings, and a really fun atmosphere. We all split pizzas + the kids drew on the walls. 😉


We didn’t waste a minute… from Gino’s, we walked straight to the American Girl place! The girls were definitely most excited for this and we spent a ton of time walking around, looking at stuff, and playing with the dolls! They loved it!


I tried to give the kids a visual before we left, to explain just how big the bean really is, but it still blew their minds when they saw it in person! If you are heading to Chicago, with kids or adults, the bean is definitely something to see. We opted to go early in the morning and were really glad we did, because there are a lot less people there an hour after sunrise.

From the bean, we checked out the cools parks surrounding it, walked along the lake, and headed on over to Navy Pier. It was a lot of walking and I think my baby-wearing, sisters’ shoulders got sore — but we still had a lot of fun + the lakeside walk was beautiful.

Once we got to Navy Pier, the other adults hung out and walked around with the babies, while I took the little girls on the ferris wheel. We decided to just send the 4 of us up, because the tickets are pretty pricey, but the girls really wanted to go. I’d say the ticket price was worth it as they got to see Chicago from high up, we had our own little gondola, and they thought it was really cool to wave to their aunt Ashley from the top!

In the evening, our hotel check-in person (surely there is a better title for her? Concierge?) told us to check out the Signature Lounge on the 96th floor of the John Hancock Center. After a lot of deliberation about what to do at night, we decided to go for it and headed to the top! We got drinks (like, sodas haha) and some appetizers at the top and checked out the amazing view. It was a great way to see the city at night and much less expensive than paying for each of us to onto the Skydeck of the Willis Tower. Ladies, if you go, you are in luck, because the best view of the city is in the ladies bathroom. It sounds funny, but seriously go check it out if you go here!

This was definitely not my first trip to Chicago and certainly won’t be my last! Thankfully, it’s a short drive for us and makes an easy weekend trip. Have you been to Chicago recently? Let me know what I need to check out the next time I go! 🙂