Somehow my family picked the all-time best weekend to be in Chicago. No joke, it was like all the stars aligned and the Windy City’s gods smiled down upon us. Our reason for going to Chicago was so that my sister could see Hamilton, in celebration of her 18th birthday. We had no idea we’d be in Chicago the same weekend as the cubbies’ historic ascent to the World Series (!!!) Like what?! It made the city feel a little more electric and Chicago really goes all out with their decorations–so the combo of halloween decs and historic statues donning cub-wear really pulled on my heart strings. Plus, Kyle Hendricks, a pitcher from the Cubs went to my undergrad at the same time as me! & On top of all that, the band Joe Keery is in (aka Steve Harrington from Stranger Things) was playing a free double-header. I’m by no means a Chicago expert, but I really love that city, and I feel like I left a piece of myself there. I don’t think it’s a coincidence that two of my absolute best friends from college are from the Chicago-area. So read on for some of my suggestions and please share your own, because I know I’ll be back soon.