Chicago is quickly climbing up the ranks on our most favorite cities in the world list. The last 2 times we have visited, it seemed like the city, people, and weather have been teaming up to sweep us off our feet. Our most recent visit was no different. Again, with beautiful weather and friendly people, here’s how Lacey and I spent an early summer weekend in Chicago.
First off, I’m a big believer in managing expectations. If you’re expecting too much out of city, event, vacation, or anything else, odds are you’ll end up disappointed if it doesn’t live up to the hype. On the flip side, if you go into something with an open mind you have a greater chance of being pleasantly surprised. This was exactly the case with us and Chicago. We had no expectations. We just wanted to hang out and eat some pizza.
We stopped in Chicago this May on our way home from our 15 day Euro-Trip. The weather was absolutely beautiful at 65 degrees and sunny. We visited a few touristy locations such as the Skydeck at the Willis Tower (formerly the Sears Tower) as well as “The Bean” (Cloud Gate) in Millennium Park. Once again, we felt safe on public transportation and found everyone we were surrounded by on the streets and in restaurants to be welcoming and friendly.
We were lucky enough to stay at the historic Palmer House hotel during our weekend in Chicago. We had some Hilton Honors rewards to burn so we decided to use them in style. A funny thing I’ve noticed when we stay at fancy hotels for free is that the employees of the hotel react to us being there the same way Clark Griswold reacts when Cousin Eddy shows up for Christmas. All that aside, we enjoyed our stay and got back at the hotel a bit by “accidentally” sneaking into an executive lounge continental breakfast. Thanks for the free waffles Palmer House!
After breakfast, we walked over to Millennium Park to check out “the Bean“. While this has become a must see for travelers and instagrammers, we had actually never been there before. As with most pieces of art we’ve been lucky enough to visit recently, Cloud Gate (the bean) was much cooler in person than we expected it to be. We ended up hanging around it for about an hour. I snapped some funny pics of Lace rockin’ cheerleader moves in front of it that you can see below.
We left Millennium Park and hopped on a metro over to the Willis Tower where we had pre-purchased “Fast Pass” tickets to go up to the Skydeck on the 103rd floor. While pre-purchasing these tickets cost us about $20 more, it saved us at least 2 hrs of standing in lines. Totally worth it. The views of Chicago and Lake Michigan from the SkyDeck Lounge are crazy beautiful. While up there, we stepped out onto the “Skydeck Ledge” which is basically a glass cube that extends out from the building and over the city. It’s a pretty overwhelming experience. As an added bonus, the 30th anniversary of Ferris Bueller’s Day Off is this year, so there is a roped off area where you can stand next to Sloane Peterson and Cameron Frye mannequins and put your head on the glass in the exact spot Matthew Broderick (Ferris) did. Getting to do this was super cool for me as I grew up with that movie.
After our nervous stomachs calmed down from being in the Skydeck, we decided it was pizza time. Eating at Gino’s East has become a “must-do” each time we visit this city. Their super deep dish, sauce on top of the cheese, traditional Chicago style pizza is amazing. Gino’s has been around for 50 years and has multiple locations but we always go back to the original restaurant on Superior Ave. This graffiti tagged, celebrity memorabilia filled pizza joint makes for a fun and authentic experience while waiting the standard 1 hour of required baking time for the deep dish crust. If you haven’t been, you need to stop by on your next visit to Chicago. If you’re with a group of 2-3 people, believe us, a medium pizza will be plenty.
Our weekend in Chicago was once again awesome. The only thing missing was a Cubs game at Wrigley Field. Unfortunately they were out of town 🙁 Next time Cubbies!
We’re becoming so fond of this city that we’ve already booked our next trip!
See you in January Chicago!
Let us know if you have any questions!
Click here to see our video edit from this trip.
Click here to see how we used rewards points to book this trip for free!