Chicago: A Weekend of Family Fun in the Windy City

We got the kids out of school early to account for the five-hour drive and the time change—our target was a 7 pm dinner reservation. We made it to our hotel with just enough time to relax before we had to head back out. We were in full tourist mode this trip, so we stayed right in the River North area, which was ideal because it put us within walking distance of many of the major spots we wanted to see.

Since we were celebrating my oldest daughter’s 11th birthday, I made sure to let both the hotel and the restaurant know before we arrived. The hotel surprised her immediately with a birthday crown, fun glasses, and a little goodie bag. Needless to say, that small gesture made her feel incredibly special. Pro Tip: It never hurts to share what you’re celebrating or ask for something to make your stay more enjoyable. The worst that could happen is that they say no.

Because she happily classifies herself as a carnivore, Joe’s Seafood, Prime Steak & Stone Crab was the perfect spot for her birthday dinner. This place started in Miami but somehow perfectly embodied “Old Chicago.” The servers wore sharp tuxedos, the walls were lined with photos of Chicago icons, and every dish was a la carte. We feasted on stone crab, a towering seafood platter, steak, and their famous key lime pie for dessert. My daughter received her own special dessert and was serenaded by the servers, which was the cherry on top. We left with full stomachs and full hearts. Once we got back to the hotel, we were all pretty exhausted from the travel day and the time change, so we happily called it a night. Thankfully, the hotel provided noise machines to help drown out the street sounds, which made for a truly restful night.

After breakfast at the hotel, we hit the street to start exploring. Our first stop was a morning coffee at the Starbucks Reserve Roastery. It has four floors (and a rooftop terrace), and each floor offers something different. We checked out each level and grabbed a bourbon barrel-aged cold brew before heading over to the Harry Potter Shop for my daughter to do some birthday shopping.

The Harry Potter shop was truly magical for the kids and adults alike. This store features a Butterbeer Bar that serves up the iconic drink and Chicago-themed butterscotch popcorn. It was where my husband happily decided to wait for us while the kids and I shopped. We definitely spent more time here than we initially wanted, but the kids absolutely loved it and came home with some fun Harry Potter souvenirs.

Next up was the Chicago Hop-on Hop-off bus. I’m a huge fan of these buses and try to ride them in every city we visit. This system allowed us to see all of the major sites first and then decide what we wanted to explore more deeply.

We hopped off at the Riverwalk so we could grab tacos and a drink at the Coco Bar. I highly recommend this place! It has great food, a shaded patio, great views, and great drinks. Since we like to ride up top on the bus and it had gotten hot, the shaded patio was a very welcome respite from the afternoon heat.

Pro tip: We knew we wanted to see a handful of things, so we bought a Chicago City Explorer Pass. There are quite a few different options, but we chose the one that allowed us three attractions.

The next place we hopped off the bus was at Navy Pier because we had reservations to ride the Seadog Speedboat tour and Flyover Chicago. My kids absolutely loved Flyover and immediately wanted to ride it again. It is similar to Soarin’ at Disney, if you’re familiar with that ride. Navy Pier has so many things to do for families that you could easily spend an entire day and night here.

While we were at the Pier, we ate an early dinner at Reunion by Chef Art Smith. It was a great Southern-style restaurant with a patio and live music. I thoroughly enjoyed my aperol spritz, fried green tomatoes, and buttermilk fried chicken.

After an early dinner, there was only one thing left to do: get dessert! So, we headed to the Museum of Ice Cream (MOIC), and it absolutely hit the spot. The MOIC is a great place for anyone who likes ice cream: young, old, families, first dates, and everyone in between. Visitors learn about ice cream through nine interactive installations and a speakeasy (yes, they sell drinks!), all while enjoying unlimited ice cream. They had some pretty cool ice cream flavors, and you can even try an ice cream hot dog complete with toppings of your choice. I won’t tell you any more because I don’t want to spoil the surprise! At the end was a famous sprinkle pool for the kids (and adults!) to play, swim, and relax in before you exit. I’m sure you’re not surprised to hear this was my kids’ favorite place. By this time it was late, so we headed back to the hotel to unwind.

Our final day in the Windy City started out with breakfast at our hotel (yay for breakfast included!) and then we headed back to Navy Pier to check out a few things we missed the day before. We didn’t have a lot of time because we were heading to the Chicago International Boat Show (CHIBS) and then had to get on the road for the five-hour trip home. With school starting the next day, we didn’t want to leave too late. If you happen to be into boats and live close enough to Chicago, I highly suggest checking out this boat show—who doesn’t like getting on fancy boats and pretending they are yours for a few minutes?

Since we were on a tight schedule, we weren’t able to actually do anything at Navy Pier; it was more of a quick sightseeing experience. We checked out the Children’s Museum, the Ferris wheel, and got a picture inside the baseball glove at Harry Caray’s Chicago. Then, it was time to hit up the boat show before we went back to get our car.

Knowing we would be in the car for a long while, we wanted the kids to be able to shake their sillies out, so we went to an amazing playground. I knew Chicago had lots of big, well-known parks and playgrounds that can get really crowded. Our goal was to find a hidden gem, and we absolutely did in Bennett Park. It’s located between E Illinois and E Grand Ave, about a block off Lakeshore Drive. It sat in the shadow of a huge apartment building, but it had everything we needed to tire out the entire family: a great playground for the kids, walking trails for the adults, and a dog park for your furry friend. The park worked its magic, and the kids were ready to sit still for the long road trip home.

Pro tip: Another great option is Lakeshore East Park. Keep in mind that it’s a bigger park, so it may be more crowded.