Weekend Getaway Road Trip: Chicago - The Cleveland Moms

For our September trip last year, we headed to Chicago for the weekend. Chicago is a great road trip destination as it’s only around a 5 hour ride depending on where in Northeast Ohio you are. The last time we went to Chicago a few years ago, we went in one straight shot but this time around, we decided to break it up & stay the night in rural Indiana on a Thursday night. We found a super cute guesthouse & enjoyed a full night’s sleep before continuing on.

We arrived to Chicago the following morning. The weather was absolutely beautiful, I was in awe. Our last trip was in the dead of winter in January & was a totally different experience. Seeing all the greenery & blue skies/lake, was amazing. Our son is a huge baseball fan so we surprised him at our first stop: Wrigley Field! When there aren’t any games, they offer tours of the stadium. This was an awesome experience I highly recommend to any baseball fan or history buff.

Next, we headed to lunch for pizza at Giordano’s. We tried this the last time we were there but I couldn’t remember my thoughts. The sauce was too thick/chunky for me personally.

Afterwards, we went to Navy Pier. Again, the sun & blue skies was an incredible sight to see. When we last visited it was so cold & not everything was open. It was great to walk all along the pier & take in the beautiful sights. There were quite a few rides & things to do on the pier but we just stuck to doing the Centennial Wheel which was a THRILL.

This was the end of our day as we headed back to our hotel. We stood along the Magnificent Mile & I ordered Lou Malnati’s for delivery which again, was still kind of too chunky for me.

The next morning, we got up early for our next activity on my agenda which I was super excited about: Chicago Architecture River Cruise. I have been wanting to do this for so long & it did not disappoint. The ride was about an hour & a half & takes you all throughout the river. Seeing all the skyscrapers from the middle of the water was pretty awesome!

Afterwards, we headed to Allstate Arena in Rosemont for what we planned this trip all around.. Monster Jam of course. The arena shows aren’t our favorite as space limitations make it hard to have a great show but it was in town so we went & had a great time of course.

Next, we swung by Pequod’s which was my ultimate favorite pizza in Chicago. Their crust is caramelized & so tasty. The sauce was thick but didn’t have chunks like the other places.

We then headed to Maggie Daly Park which was really weird for me because I remembered it as this giant playground because my son was younger when we were last there & with new eyes, it didn’t seem that huge. It was really strange for me & an eye opener about perception based on how old/young your kids are. Anywho, we also swung by The Bean but it was closed off due to construction. We were still able to view it but with some obstructions all around.

Lastly, we headed back to our hotel & then went back out when it got dark to take in the sights of the skyline all lit up. On our riverboat cruise, they mentioned how one of the buildings was all lit up white & we wanted to get a glimpse of that. It was a great way to spend our final night in Chicago. Side note: unbeknownst to us, it was Mexican Independence Day which is a big deal in Chicago & also quite chaotic. Roads were blocked by unofficial car parades & I am very lucky that we were within walking distance of the river that night because it was absolute chaos all night long.

Before heading home, we stopped at the infamous Stan’s Donuts which was pretty good but not that mind-blowing to me but worth a stop if you’re there!

& that was it! Chicago is a great weekend destination for any Clevelander. We are looking forward to our next trip back!

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