I’m back with a continuation of yesterday’s post!
I recently traveled back to Michigan to attend my college roommate Kendall’s wedding, and I figured I might as well take advantage of the current remote work atmosphere and make a full week-plus out of it.
I also really wanted to show Ryan around Chicago! He’d only been once for a few hours back when he was a teenager, and since I spent a good chunk of my 20s living in Chicago, I wanted to spend a few days showing Ryan some of my favorite places and introducing him to my friends.
So, we did that!
I also — selfishly — wanted to kind of laugh a little at Ryan being so out of his element. It’s only fair, since he teases me quite a bit about my city-person tendencies, given that I now live in the mountains and all.
Ryan and I left Michigan after stuffing our faces with Timbits and black coffee. We got to Chicago, dropped our stuff off at Jake’s place and then met up with my CorePower Yoga friends for dinner at Beard & Belly up in Edgewater. Then we went back down to East Lakeview (where Jake lives, and we were staying) and grabbed drinks at DryHop.
Then we went to bed, because we’re both like 80 years old, Ryan spent the entire day hungover, and we had a lot of plans for Monday.
I took both Monday and Tuesday off of work so I’d have plenty of time to show Ryan around. Granted, it’s really hard to do a full tour of Chicago in less than two days, but we had time to visit a few of my favorite places.
We started Monday morning with breakfast at Tweet… of course.
Then we hopped on the L and headed downtown. I showed Ryan my old office and then we did all the super touristy stuff — the Bean at Millennium Park, Grant Park, Mag Mile, Navy Pier, etc.
We stopped for drinks at Billy Goat Tavern (of course) and then ended up making our way back to Jake’s so we could go to Hopleaf for dinner and beer.
We did take “the long way” home by riding the Brown Line ALL around the Loop so Ryan could take in the city lights at night, which was pretty fun. It’d been a while since I’d done that!
Hopleaf was one of my FAVORITE restaurants when I lived in Chicago, so I was really excited to force Ryan to eat CB&Js and mac and cheese.
And, that was it. Ryan had to leave Tuesday morning, so we went back to Jake’s for the night.
On Tuesday, I rode the Blue Line out to O’Hare with Ryan, said goodbye, and then went to go grab Ramen at Wasabi with my friend Mickey for the afternoon.
That was kind of about it for the trip! I had to work both Wednesday and Thursday, so short of dinner at Parson’s on Wednesday and lunch at Cheesie’s on Thursday right before my flight out of O’Hare, that was about all I really did during my few days in Chicago.
Overall, it was a pretty good trip. I wish I’d had a few more days to drag Ryan around to museums and non-North Side/ non-Loop neighborhoods, but I did what I could in the time that I had.
It was really weird to be back in Chicago, to be honest. I kept expecting to miss it and want to move back immediately, but I… didn’t? It felt kind of nostalgic and just weird in a way I can’t fully express.
It was definitely great to see most of my Chicago friends after a few years away, though!
This post was originally published Jan. 22, 2022. Its timestamp has been updated.
