The Create & Cultivate conference this August brought some of my friends (Sarah & Mitra) and I to Chicago. It was my first time and I already want to go back! The city had more skyscrapers than I imagined, making it one of the most beautiful skylines I’ve ever seen. While our stay was short, we did a lot of exploring and I’m so excited to share it with you all!

View from our room in the Kimpton Hotel Monaco Chicago.

Stay
We stayed at the Kimpton Hotel Monaco Chicago, a boutique hotel located in downtown Chicago. I love every Kimpton hotel I’ve ever stayed at, but the Kimpton Hotel Monaco in Chicago had a very unique charm to it. The design and decor of the lobby and our room were so chic! We had a gorgeous view from our room of the city and the water. We especially loved the location of this hotel because it was only a few minutes away from the Chicago Riverwalk by foot and a very short drive to the Navy Pier – both places we had on our list of places to go!

Besides the location and aesthetic of the hotel, we were very impressed with the service. Like every Kimpton hotel I’ve stayed with, all the staff at the Kimpton Hotel Monaco Chicago were warm, inviting, and accommodating to all our needs – from giving us recommendations to making reservations and booking tickets.

I actually prefer to stay with boutique hotels, espeially the Kimpton because there are amenities you wouldn’t typically get in other hotels today. They offer bikes if you’d like to explore the city with them, a hosted wine hour every evening where you can meet other guests, and of course coffee and tea in the morning to kickstart your day!

Bathroom decor of the Kimpton Hotel Monaco Chicago

Eat
The restaurant inside our hotel, Fisk & Co, is a great place for if you like seafood. The bistro has the same chic decor as the rest of the hotel. We also had lunch at Three Arts Club Café, probably our favourite meal the entire trip! We waited two hours for a table and it was well worth it! This restaurant is located inside the same building as Restoration Hardware so we browsed each floor while we waited. Time passed by quickly because each floor was so beautiful – if you have an appreciation for interior design, you’ll love it too! When we finally sat down, I had what I would describe as one of the best salads in my life, in one of the most beautiful settings I’ve dined at.

Another favourite meal of ours was Chicago deep dish pizza. We couldn’t not have deep dish pizza our first time Chicago, so we set out to find some for a later dinner one night. We found ourselves at Giordano’s and were not disappointed! You can build your own pizza here and we recommend coming with friends because it’ll be very, very hard to finish it alone. A meal totally worth it!

I mentioned that Chicago has a beautiful skyline, which is why we had to have a drink on a rooftop to take in the view. Two places that have beautiful views are Cindy’s rooftop with panoramic views of Millennium Park and Raised, an Urban Rooftop Bar which is an indoor/outdoor bar with a private VIP greenhouse overlooking Chicago’s skyline.

Play
The place that was actually on the top of our list when planning our trip was actually the Cloud Gate sculpture, also known as the “bean”. It is one of the highlights of Millennium Park and made of 168 highly polished stainless steel plates so I’d recommend coming here to take a photo. You can get a photo of a reflection of yourself and the city skyline, it makes a good memorable vacation photo!

While some may not call this “play”, we actually also made reservations in advance for SoulCycle. We knew we’d be having Chicago deep dish pizza and other indulgent eats, so we wanted to balance it our with a fun workout. Since we are all long time riders at SoulCycle, we knew we’d have to do a class while we’re in the city.

The last place I’d recommend is Skydeck. It’s an observatory located on the 103rd floor of the Willis Tower. Thew view from up here is UNREAL and the observation decks are glass boxes that make a great vacation photo as well. I’ll warn you though, you’ll have to make it quick one – they gave us each literally 20 seconds to take a photo!

While this was only a 2 day trip, I’m glad I got to see so much of the city! I will definitely visit again to see the spots I missed. Be sure to let me know your recommendations if you have any!