Last weekend I went to Chicago to visit my best friend. Caitlin moved there last April, and this was my first time being able to go visit her (in large part due to our amazing travel schedule!). Though I’ve flown through ORD dozens of times, this was my first time getting to experience the wonders I’d heard about Chicago. The biggest bonus was getting to see it all with Caitlin!
After landing in the early afternoon on Friday and taking “the L” to Logan Square, we had a quick turnaround to make it to yoga class at Caitlin’s studio with her favorite yoga teacher. Getting to flow it out at Zen Yoga Garage was the best way to shake off a long flight.
Another quick turnaround of a shower and change and then we sat down at the bar at Lula Cafe, Caitlin’s favorite, for an early and delicious dinner. We followed this up with toddies at Longman & Eagle, a local whiskey bar, where we proceeded to discuss the intricacies of entering Narnia with our mustachioed, mulletted, tatted, beanie-wearing bartender. We’d planned to include a jazz/ blues show in our evening plans, but ended up electing to take our reunion back to the apartment where we celebrated Friday night in true Liz & Caitlin style: dance parties and watching Sex & the City.
Life’s not as glamorous as you think it’s going to be. But it’s way more fun.
We woke up on Saturday to a rainy day that Caitlin blamed on me. (From rainy weather to train delays, there was a lot of “this never happens” while I was there.) We spent the morning eating Caitlin’s favorite blueberry cereal bowls in bed and watching Mighty Ducks – classic.
After a stop at Intelligentsia for coffee, we caught an uber downtown, with plans to go to the Art Institute and The Bean (the one thing that was really on my Chicago list). With it pouring rain and seeing a line all the way outside the museum, we turned right back around to go to lunch in Wicker Park. We wandered around Myopic Books, an amazing used bookstore, while waiting for our table at Dove’s Luncheonette.
The afternoon was spent in a lovely haze of watching Sex and the City and resting for quite the Saturday night ahead. Caitlin warned me that Chicago was a late night city, so I came prepared with requests for an afternoon nap beforehand.
8:30pm: The Up Room
Before dinner, Caitlin and I grabbed a glass of champagne in the bar at the top of The Robey, the tallest building in Chicago. The idea was to get a nighttime view of the skyline, but of course it was still rainy and so we couldn’t see a thing. But still a lovely way to kick off the evening.
Caitlin and I met her beau for a lovely pizza / pasta dinner at etta in Wicker Park. We nommed on scallops, spicy cauliflower, wild mushroom pizza, and squid ink mafaldine. Not to mention wine, coffee, and chocolate tart.
12am: The Violet Hour
Erik took us to a nearby cocktail lounge. There’s no sign outside, just a door that opens to a dark hallway with a bouncer waiting. After saying the magic words (mostly kidding), we were led into an amazing lounge with tall-back chairs, high ceilings, and dim lighting. Supposedly this is the bar that was the first in Chicago to start experimenting with cocktails. And I have to say the drinks were unique – we didn’t even recognize half of the things on the menu.
2am: The Revel Room
We took our energetic selves to an “after hours” bar where we got our groove on in the Silver Fox Den.
I’ll fast forward and say that it was 6:30 before Caitlin and I crawled into bed.
A few hours later we were back at it. After coffee (because duh), we finally made our way back downtown. The sun was out, perfectly displaying a surprisingly clean city as we walked along the river. I have to say I think this was my favorite part of Chicago. The juxtaposition of the river running right through all of these huge buildings and being able to walk right alongside of it is so unique.
This walk led us to The Bean, the one thing in Chicago I wanted to see. Other than Caitlin, of course. I suppose I had high expectations of this art installation, and I wasn’t disappointed. Similar to the river walk, it is set right in the middle of a city park, the sun glinting off of it’s shiny silver surface.
From there, it’s just a short jaunt over to the Art Institute of Chicago, where we spent hours wandering through thousands of years worth of art. We spent most of our time in the contemporary and modern areas, with a final necessary stop in the Impressionist wing.
Unexpectedly I’d say we most enjoyed the paperweight collection and the tiny room exhibition.
We took our culture-weary selves back to Wicker Park for a late lunch / early dinner at Clever Rabbit.
Our plans to watch the Oscars at the Logan Square Theatre failed as we were too late to get seats, but that ended up being a great thing. We were able to stream it and curl up on the couch at home.
Our last morning together we got breakfast at Lula and coffee at Intelligentsia before we both flew out separately.
It was the perfect Chicago weekend. Classic Liz-and-Caitlin style where we definitely did a lot of things but still had plenty of chill time. And I got to experience some quintissential Chicago things. It also got me really excited for next time! I even have a little list going already:
- Music at Green Mill
- Chicago-style pizza
- A Cubs game
- Lake fun (might need to wait for warmer weather for that)
- Run along the 606
- A show at the amphitheater
Want to see more of my trip? Check out my Stories!
Extra bonus! Caitlin is coming to Portland next week!