Chicago has long been on our must-visit list and this past September we decided to be spontaneous and book a last-minute flight. (And by last-minute I mean a mere four weeks out, crazy I know.) As I sat down to plan our trip using my handy Notes app on my phone, I was so excited the weekend came together faster than I anticipated. Mainly because Chicago has so much to do in one walkable magnificent city! Read on to see how we got a taste for the Windy City.

Batter up! Catch a Cubs game.

Why yes, we did book a flight to Chicago based on the Cubs’ schedule. Visiting Wrigley field has been on our bucket list ever since I took Jake to Fenway park summer of 2018. And while Wrigley field isn’t as old or as historic as Fenway, the vibe was nearly as amazing. There is just no comparison to Cubs fans. They sing louder, beer more, and cheer harder.

Check out the Bean at Millennium Park.

A visit to Chicago would not be complete without a photo (preferably a selfie) at the iconic Bean. While construction surrounding the Bean is currently underway, it is scheduled to be completed in the spring of 2024.

Stroll the Riverwalk and Navy Pier.

Get your steps in and stroll through down the Navy Pier where you’ll find shops, restaurants and the Shakespeare Theatre.

Visit Goose Island Brewhouse.

Located in the historic Lincoln Park, Goose Island Brewhouse was founded in 1988 and is the longest continuously operating craft brewery in Chicago. As Jake’s favorite IPA beer, visiting this rustic brewery was a must-do.

Until next time,

Leah Ost