Jesse Takes A Weekend Trip To Chicago

Written by on December 4, 2023

Over the last few years, Chicago has become quickly become one of my favorite places to visit. And getting to see the city all dressed up for Christmas made it the trip that much more spectacular.

So, a little back story: My girlfriend Katie is a big fan of Brett Eldridge. And every holiday season, Brett goes on the “Glow” tour. He’s originally from Paris, Illinois so his stop in Chicago is treated as a hometown show.

I decided to surprise Katie with tickets to the show as her Christmas present this year and as a bonus, we got to see some sights we hadn’t seen before.

We got into the city Saturday afternoon and after checking into the hotel and a quick bite, we took a stroll through Millennium Park and got the best glimpse of The Bean as we could. (The site is under construction)

We then took in the sights up and down Michigan Avenue and killed a little time before our early dinner reservation. While we still had some time before the show, we stopped by the Chicago Athletic Association Building where we accidentally stumbled across a Christmas-themed pop up bar called Happy’s.

“Happy’s” was basically modeled after your Grandma’s basement during Christmas. Fake paneling and all. Of course, Old Style and Schlitz were the beers available.

Then we made our way over to the Chicago Theatre. Now, I had never been there and I was absolutely blown away.

Now, let’s talk about about the show. If you’re unfamiliar with Brett’s “Glow” album, it’s very much in the Big Band, crooner style. All while telling stories about Christmases with his family (whom were in the crowd). It was just a feel good show and if you left without being in the spirit of the holiday, you weren’t doing it right.

All said and done, it was a fabulous time in the Windy City. We were exhausted by the time we got home but would absolutely do it again in a heartbeat!

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