Our Family Chicago Staycation

Friday, August 30, 2019

Sometimes things don't work out how you plan or want. This is life. And sometimes, if you get out of the way and let go of your plans, life will surprise you with the best gifts.

Originally our last vacation of the summer was supposed to be to San Diego. But due to scheduling conflicts, we had to cancel that trip. And while I was a little sad, okay maybe a lot sad, I was pleasantly surprised by how much fun we had on our Chicago staycation. And now we have a new family tradition - a Chicago staycation before going back to school. It's not just a stay-cation, it's a Chi-cation!

As the saying goes, “In Life, It’s Not Where You Go, It’s Who You Travel With” – Charles Schulz. And let's be honest, Chicago in the summer is just the best city ever. Here are a few highlights from our family's Chicago Staycation.

Where to Stay

DoubleTree by Hilton Hotel Chicago - Magnificent Mile

Recently renovated, the DoubleTree by Hilton provided the perfect home away from home for our family. The location in Streeterville, on the corner of Ohio and Columbus, was terrific and within walking distance of some of Chicago's top attractions.

We booked a one bedroom suite, which allowed us to put the kids to bed and still stay awake without disturbing them. The room was beautifully furnished and with a small kitchenette and table, it was easy to enjoy some meals and snacks in the room.

The kids' favorite feature of the hotel was the rooftop pool. (Well, that and the cookies you get when you arrive.) It wasn't a big pool, but situated amongst the tall towers of Streeterville, it had a distinctly unique and exclusive feel to it. A very family-friendly hotel, I was really pleased with our entire stay here.

What to Do

Maggie Daley Park

Just a short walk along the lakefront from our hotel, Maggie Daley Park is a magical and adventurous park in the heart of downtown. Our kids love this fun-filled park. We come here often in the summer, but on this trip we went all out and experienced everything there is to do at the park. Our 5-year-old wanted to try rock climbing, so we headed over to the climbing wall and they got her all set up with gear and had a very friendly instructor ready to help her try it out. She loved it and I am sure we will be back to do it again.

Lately the kids have been requesting to go mini golfing. I blame their father. So we all played a round at City Mini Golf. It was ideal for little kids because the holes are pretty easy and they got a kick out of all of the Chicago-themed holes. And bonus, we won a free round of golf at the end when we returned our balls!

We ended our day at the park with ice cream, watching screaming kids run through the spitting faces at Crown Fountain in Millennium Park. To our relief, instead of joining in, our kids voted to head back to the hotel and go swimming in the pool.

Chicago Children's Museum

I am embarrassed to say that we had never been to the Chicago Children's Museum before this trip. But I hate driving to and parking at Navy Pier, so I have always avoided it. Walking to the museum from our hotel was ideal and the kids had a blast at the highly interactive museum.

I think that my youngest could have spent the entire visit playing fireman at the fire station exhibit, but they also took a stab at building structures, digging for dinosaurs, experimenting with different sounds in the Sound Playground, and of course, our oldest loved the adventure of climbing through the multi-level ropes of the Climbing Schooner. We had a great time and may have to brave the traffic to come back again before our next staycation.

Navy Pier

After exploring every inch of the Children's Museum, we headed out to the circus that is Navy Pier. The kids wanted to ride every ride they saw, but we ended up choosing three: the carousel, the swings and obviously, the Centennial Ferris Wheel (which is worth the price of admission for the views alone!). We also enjoyed one of my favorite Chicago legendary foods - a bag of Garrett's cheddar and caramel popcorn mix.

Originally we planned to stay until the fireworks, but after a full day of playing, the kids (and grown-ups, if we're honest) were beat. So we decided to head back to the hotel. But if you can muster the energy, Navy Pier puts on a great fireworks show over the lake every Wednesday and Saturday night.

The Magnificent Mile

If you're going to play tourist, you may as well go all the way. So on our last day of staycation, we walked down the Mag Mile and let the kids go into a few shops. They, unsurprisingly, picked the Disney Store and Dylan's Candy Bar. After picking one souvenir each, it felt like a very sweet way to end our little staycation.

Where to Eat

Chicago has an incredible and delicious food scene. But with two picky eaters along, we ended up at kid-friendly spots that we knew would keep our littles happy. For breakfast, we ended up eating at the hotel most mornings. The DoubleTree's breakfast buffet was convenient and surprisingly tasty. We also had a sweet surprise one morning and the kids woke up to donuts from Stan's Donuts.

For dinner we picked two tried and true kid-friendly spots:

Jake Melnick's 

Located just off of the Mag Mile, Jake Melnick's is a great spot to grab some barbeque. I highly recommend starting with their fried pickles and wings! It's also a sports bar, so loud kids go pretty unnoticed. And if you can, try to grab a patio table to enjoy the all-too-short summer weather in Chicago. 


When in Chicago, you have to get pizza. Pizano's, located just a few blocks from Millennium Park, dishes up some of the best pizza in Chicago, both deep dish and thin crust (we actually prefer the thin crust). And if you can save room, their Holly and Little Rudy's Chocolate Chip Cookie is a delicious way to end the meal.

Getting Around

My favorite part about any staycation, especially when kids are in the picture, is that when your destination is only 30 minutes away, you don't get a million "Are we there yet"s. You get one and then you literally are there.

The beauty of a staycation in Chicago is the walkability of the city. From our hotel, we were easily able to walk to Millennium Park, Navy Pier and Michigan Avenue. I loved that our hotel was near the lake and we took quite a few breaks to just play in the sand on the beach.


We were also able to easily hop on and off the CTA busses when the kids got tired of walking. I think they thought the bus ride was an adventure in itself!

Water Taxi

I also had on my list of things to do to take the water taxi from Navy Pier over to the Shedd Aquarium (one of our favorite destinations in Chicago). But we ran out of time, so that will just have to wait until next year.

As the kids get older, I can't wait to add on even more fun adventures to our staycation. I picture us heading up to Wrigley Field for a Cubs baseball game or catching a Broadway in Chicago show. Chicago really is a fantastic city. I loved having the opportunity to play tourist for a few days and I love that we have a new family tradition to look forward to each year!

“It’s a 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes; it’s dark and we’re wearing sun glasses. Hit it!” - The Blues Brothers

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