A couple weeks ago, Kayla and I realized that we had the same spring break for the first time in forever and decided to plan the perfect weekend getaway to Chicago! For those that don’t know, Kayla and I have been best friends since the beginning of preschool when we were just 3 years old. When we were younger, we went on trips to Chicago almost annually with our families (the good old days filled with trips to the American Girl Place), but we hadn’t been back to the windy city together since we were 10 years old. I was looking so forward to a weekend of site-seeing, mimosa brunches, and some much needed catching up with my bestie!
Early Friday morning, after I left from Toledo and Kayla left from Kalamazoo, we met up in Indiana to drive into the city together and check into our Airbnb.
We made reservations on Airbnb at the Dewitt Place Hotel and it did not disappoint! We chose it for it’s perfect location, right behind the John Hancock Building and one block away from the Magnificent Mile, so that we didn’t have to Uber as often. It was an old, classic style hotel and our room had the most gorgeous view of Lake Michigan right off the Gold Coast. We both said that whenever we decide to come back to Chicago, this is where we’d stay again without a doubt!
After checking in and dropping off our luggage, we headed out to the Magnificent Mile for some shopping and lunch. We honestly couldn’t have picked better weather; the entire weekend it was 45 with cloudless, sunny skies!
After lunch, Kayla kept noticing people walking around with Argo Tea cups and insisted that we find the shop so I could try it. Once we found it a little ways down on Michigan Ave, she recommend I try her favorite, the Carolina Honey iced tea. Just to give you a reference of how good this tea was, I admitted it was better than any Starbucks iced tea (and I love my Starbucks).
We even stopped in again one more time before we left on Sunday because it was just THAT good.
Later that evening, we headed further down Michigan Ave. for a sunset view of Cloud Gate. Plus, no trip to Chicago is complete without pictures at The Bean, right?
After a day of site-seeing, we walked back to our Airbnb to get ready for the night. We were in dire need of some Chicago Style Pizza in our lives so we headed out to Gino’s East for dinner and then Ubered over to Old Town District for what ended up being one of our favorite parts of the trip!
While we were planning our trip, both of us received recommendations from our friends for The Second City Comedy Club right downtown. We both thought this sounded like the perfect night out so we bought tickets for our first night there! Before the show, we stopped in Corcoran’s Pub right across the street for a couple drinks.
The Second City is an improv comedy club and it. was. hysterical!! Kayla and I both said that it reminded us so much of the show Whose Line Is It Anyway? They brought people from the audience up on stage for some skits and took audience suggestions for others. At one point, they even asked Kayla who her celebrity hall pass would be and after she answered correctly with Channing Tatum 😉 they proceeded to act out a skit revolving around Channing Tatum. 11/10 would recommend.
The next day we got up, got ready, and walked to…
…for the absolute best brunch and mimosas!
I had brioche french toast with blackberries… can you say yum?!
From brunch, the Chicago angel wings mural was just a short walk away so we headed that way!
After getting super lost during a subway experience four years ago in NYC, my mom, grandma, aunt, cousin, and I all made the decision together that subways were just not for us. Kayla, on the other hand, is a little more confident than myself in tackling city life via a subway or L train (and not getting lost) from her many trips to NYC and Chicago through the years. Just as we were about to order an Uber to go spend the afternoon in Wrigleyville, Kayla said “you know what? Lets take the subway, we can do it” and I followed her lead!
We hopped on the nearest L train and as we got off to catch the connecting subway route to our destination, we noticed that we had been dropped off right in front of the Chicago Theater! It was perfect site-seeing along the way.
Once we walked around Wrigleyville and I got to see Wrigley Field for the very first time (now I especially want to come back for a game), we stopped in Sluggers for a couple drinks!
While planning our trip, my roommates recommend Howl at the Moon dueling piano bar. So, for our last night there, we went out for a late dinner and then walked down the block to find this place…
The music was a blast, the drinks were amazing, and the place was packed with bachelorette parties! Needless to say, it was a perfect night out with my best friend.
On our final morning there, we checked out of our Airbnb and walked next door to the cutest little coffee shop, Dollop Coffee Company, for lattes and breakfast.
After breakfast, we had just a couple more places to see and things to do before we left (like drink more Argo tea). We walked down the Magnificent Mile and explored Maggie Daley Park to wrap up our trip.
This past year, Kayla and I really haven’t had as much time to catch up and see each other as we’d like since we’re both busy in grad school. This weekend getaway was exactly what we needed and I’m already counting down the days until we plan our next weekend trip together!
Until next time, Chicago