Weekend Destination: Chicago


chicago night skyline. Des Moines MomI have started a summer tradition of doing a “yes day” or a mini trip for my school-aged child. It’s her reward for working hard at home over the summer while her parents both  worked from home. This year, we planned a girl’s trip with my sisters to Chicago. We spend all summer planning, saving, and dreaming about how we will spend our saved pennies.

How to get there

I wanted to fly for our trip because it’s so fast, but the summer brought uncertainties with plane travel. Even with higher gas prices, we favored driving for the flexibility and independence it brings to our timeline. I secretly love the toll roads because they don’t have any traffic and you can pay the tolls online later. The payout comes out to about the same, but I am very happy we drove. Plus, it meant we could stop at the Chicago Premium Outlet Mall on our way home.

Also, the drive was part of the fun. We left early on Friday and were home by dinner on Sunday. It helped that we purchased this fun license plate game that the adults enjoyed more than the kids.

Where to stay

I ended up getting us a hotel room right on Michigan Avenue and as a result we were able to walk almost everywhere. In the past I have chosen a hotel that is somewhere near the Chicago Train Authority line stops. This is a cheaper option for the hotel but adds time for travel.

Since my daughter was with us, we wanted to minimize the travel stops and I am glad we chose that option.

What to do

Some of the top destinations for families include a baseball game at Wrigley Field, quality shopping, Shedd Aquarium, The Art Institute, the Field Museum, and so much more. There over 60 museums in Chicago so I’m confident you can find what fits best for your family.

This was a girl’s trip, so we focused on shopping and fun experiences. We took a dinner cruise on Lake Michigan and watched the sun set behind the city skyline. There are a variety of lake and river cruises that can show you a lot of the city while you relax.

We also did A LOT of shopping, and the highlight was the American Girl Doll Store. There are only a handful of the physical stores left and we ended up spending hours there. My daughter and her doll got their hair done, we had a lunch together, and even got her doll’s ears pierced. It was almost like a museum for each of the dolls. My sisters came along for the lunch, and it was our favorite part of the trip. Just be sure to book in advance.

What to Eat

I won’t get into any arguments about which Chicago style pizza is the best because there is no right answer. I’ve had them all and (braces for you to throw things at me) they are all delicious. Choose one at a convenient location to your travel stops and enjoy that delicious deep dish.

Be sure to grab some Garrett’s popcorn, which can also be found at souvenir shops. But a MUST VISIT location is the IT’Sugar Candy Store on Michigan Avenue. It was a magical place for all of us. They had a variety of vintage candies which gave me flashbacks to scouring the candy aisle at Casey’s when I was a kid. Even if you don’t leave with a purchase, it’s worth a stop.

Have you been to Chicago? What are your favorite things to do there? 


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