Finally sharing my recommendations for 24 hours in Chicago! Mitch and I recently traveled to a Chicago suburb for a family wedding and jumped at the opportunity to spend a day in the city. Fun fact– I actually was born right outside of Chicago and lived there until I was 7! I had not been back to the city as an adult and oh my gosh I fell in LOVE with it. If it didn’t get absurdly freezing during the winter months I would 100% consider living there.
We hopped off the train at union station at 9am and were immediately taken back by the gorgeous views of the city. It is wild seeing such a huge body of water surrounding a city skyline. We started off our morning with Starbucks and decided to head toward Millennium Park. As touristy as it gets, I know, but it really is a must do for first timers in Chicago!
Of course we got the classic photo by the Bean, but Millennium Park has a lot more to offer than that as well! It is surrounded by hidden gardens and more architectural art.
We also walked through Grant Park and saw the Buckingham Fountain. Let me tell you, this fountain is GIANT. It really took us by surprise how big it was, and it was accompanied by gorgeous views of the city skyline.
After walking around for awhile we decided it was time to get brunch, we were starving! I have heard the best brunch in Chicago is at Cindy’s. It’s a rooftop restaurant that has an amazing view of Millennium Park. Unfortunately, reservations book weeks in advance so we weren’t able to go there! (make sure to reserve far in advance!) Definitely on the bucket list for next time.
We decided to try out a cute rooftop called the J. Parker rooftop lounge. This was an adorable rooftop with views of the Gold Coast District. The view was amazing, Lake Michigan washes up to a manmade concrete beach with sand, where people sunbathe, jog, play beach volleyball and relax. It was such a cool vibe to see a huge city have a beachy feel as well. We had a few mimosas and some truffle fries (highly recommend!!)
Next time were in the city we definitely want to explore the Gold Coast area more and walk down by the “beach” unfortunately for us it started to thunderstorm so we weren’t able to do that this time around. Also not too far from the Gold Coast is Lincoln Park which is home to the Lincoln Park Zoo, which is one of the only free Zoos left in the country. I have so many memories here as a little kid and definitely want to go back next time!
We Ubered to our next stop Fig & Olive (because one brunch spot just wasn’t enough) I was dying to try their avocado toast! They have a super cute rooftop as well, but since it was storming we sat in the main dining area inside, which was also super cute and very cozy! The avocado toast was some of the best I have ever had and their bread and olive oil assortment was amazing as well. I enjoyed my avocado toast and bellini before we headed out to Oak Street for Shopping!
We spent the next couple of hours shopping and exploring up and down Oak Street and Michigan street (The famous Michigan Mile!) Before stopping for an early dinner before we had to head to the airport. We decided to eat at Eataly because I am a huge sucker for Eataly! I’m sure there are more cool local spots to go to, but we were hungry, it was raining and Eataly is too good to pass up. We ended up splitting burrata and pistachio ricotta ravioli before inhaling some incredible cannolis.
If you have never been to an Eataly you need to go! They have locations in a few big cities, I have been the the New York city location a ton, it is basically a marketplace of incredible Italian food and wine that also has multiple restaurants and counters to dine at. I highly recommend going at least once!
We then headed back on the train to the airport! (there is a train that takes you straight to O’Hare from the city which we found super convenient!) Our flight ended up being delayed 7 hours so we slept on the airport floor and got home at 5am the next morning but it was still worth it! We can’t wait to make it back to Chicago and I would love to hear any recommendations anyone has for our next visit!
shop my outfit here: