The first city we flew to with our girlfriends was to Chicago! We still talk about how it was one of our favorite cities. There is SO much to do and see and we couldn’t get enough! Between it’s beautiful architecture and amazing food, we never wanted to leave!
We had a evening flight so we were able to check into our hotel Hilton Garden Inn Chicago in North Loop immediately. It was the perfect location since it was walking distance to almost everything we wanted to do and we were right by the river! We quickly changed out of our airport clothes into classier outfits and headed to Cindy’s Rooftop for some rose to kick off our weekend getaway!
Our first full day in Chi-town was all about exploring! We started with a not so healthy but ever so fulfilling breakfast at Doughnut Vault. There isn’t a bad tasting donut there! After carbing up, we walked around the city passing by the river and arriving to The Bean! There is also a beautiful garden right near there. We grabbed some apps at Bridge House Tavern right on the river however that was recently closed. We heard the River Roast is amazing though! We then headed to Skydeck, which is a glass box that extends four feet outside the 103rd fl of Willis Tower! If you’re anything like Courtney, she was having a blast! If you’re anything like me, I was crying inside. It’s definitely an experience! We grabbed some much needed coffee and headed back to the hotel to change for the night. We grabbed pre-dinner drinks @ RPM Italian and if you love E!News then you know we were secretly hoping to run into Bill & Giuliana! As we were going to leave, the girls surprised me with dinner there for my birthday! We originally couldn’t get a reservation but little did I know they already had one! It was so sweet! After a delicious dinner & dessert, we went to a super cool speakeasy Three Dots and A Dash for insane tiki drinks! Out of our four drinks, only one or two of them were actually good, but at least they were pretty LOL! Our next round of drinks happened at 360 Chicago. We were able to snag a table right near the window and took in the amazing nighttime view.
We slept in a little and did more exploring around the main city before heading to lunch @ Giordano’s for some deep dish pizza YUM! You can also eat at Lou Malnati’s for a good pie, too! We walked to Navy Pier and enjoyed some sangria taking in all the beautiful views of the city. We scheduled an Architecture Boat Tour, which was one of our favorite parts of the trip – it’s definitely a must do! It was time to change for the night and head to London House to enjoy the sunset. We jumped in an uber to Lincoln Park to grab an amazing meal @ Café Ba-Ba-Reeba. Before leaving the area, we enjoyed the summer weather at J. Parker, a young rooftop bar. On our way to Joy District and Upstairs, we even stopped by Wrigley Field to snap a drive-by pic!
We packed up our bags before we started our last day in the Windy City! We ate at the amazing Girl and the Goat for brunch and then explored Chicago’s Botanic Garden. After spending a couple hours there, our appetite kicked in again and we enjoyed our last meal of the trip at non other than Santa Monica Summer House. We did have to wait a little for a table but didn’t even mind because the restaurant is so pretty and even has a little bakery section where we indulged in dreamy giant cookies.
When we go back to Chicago, we’ll definitely be sure to include RM Champagne Salon and The Gangster Tour. There’s also a ton of amazing restaurants including Purple Pig, Nico Osteria, Publican, HUB 51, Beatrix & West Egg Cafe!
Looking for more travel inspo? Check out our travel guide to Nashville!
P.S. Photo credit to Dayna for some of these awesome pics 🙂