Chicago Quick Trip

Over Memorial Day weekend, my good friend Jess came to visit good ‘ol Illinois. We took a very short trip to Chicago, took some photos and thought I’d share!

Since we were staying overnight, we needed a place to sleep. We hit the jackpot when we found a vintage Airstream available on Airbnb. Jess and I both had wanted to stay in one, so booking this was a no-brainer. It turns out that our Airbnb hosts were some of the most warm, kind and hospitable people I’ve ever met, and after chatting with them over the two days we stayed with them, they’ve left a permanent impression on us. So thanks Andy and family!!

When we weren’t hanging out with our awesome Airbnb hosts, we were in the Loop, doing some sightseeing and meeting up with some old friends. On our first night in the city we grabbed a snack at the Berghoff, a historic German restaurant, then passed by the Willis (what will always be the SEARS, to me) Tower, the Cloud Gate (the “bean”), Millenium Park where we caught part of a concert at the Jay Pritzker Pavilion, the Lions at the Art Institute and picked Buckingham Fountain in Grant Park as our meeting point with the rest of our group. After grabbing a few drinks, Jess and I headed out for famous Chicago pizza at Giordano’s.

On day 2 we did more wandering. Since we were short on time we mostly stuck to free, outside, walkable attractions. We spent quite a bit of time on Michigan Avenue and the Magnificent Mile where we saw the Chicago Avenue Water Tower and Pumping Station. We headed up to the Signature Lounge in the Hancock Building for brunch and impressive views of the city. After brunch we wandered by the Tribune Tower and discovered some free fun at the McCormick Bridgehouse & Chicago River Museum. We finished the day wandering along the Chicago River and making a quick visit to Navy Pier.

The highlight of the entire weekend for me, though, was running into the Puppet Bike. This is a one-man show that might just be the happiest place on earth. If you’re ever feeling down, just pull up some Puppet Bike videos on YouTube or search #puppetbike on Instagram and I bet you feel better.


Overall it was a great, quick visit to the Windy City and it was fun to show a visitor around! What’s your favorite Chicago attraction? Tell me in the comments!

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