Chicago Travel Guide


Chicago, Illinois, is my favorite big city in the U.S. After spending 3 days in the city in May of last year with my amazing best friend, Amanda, this city has forever found a place inside my heart. Below is a look at where we stayed, what we ate, and what we experienced:

Day 1: We check in at The Drake hotel, hit up Kanela Breakfast Club for brunch, take a stroll past Northwestern‘s downtown campus, then get ready to head down to our Architectural River Cruise.

Architectural River Cruise: The cruise is a DREAM and is a must for your trip to Chicago. You learn so much about the city in such a short amount of time and experience spectacular view after spectacular view.

After walking past the Centennial Fountain, we head to the Navy Pier, then hop a ride to Wrigley Field and catch the last few innings of the game at the Brickhouse Tavern. From Wrigley, we head to Eataly, which was easily one of the best meal experiences I have ever had. The Aperol Spritzes were divine, the pasta beyond compare, and the dessert bar was the perfect icing on the cake. Following dinner, we headed to the Green Mill Cocktail Lounge, Al Capone’s old haunt, which was so neat, but packed to the brim on a Saturday night (make sure you have cash!).

Day 2: We’re up early and ready to head to the Art Institute of Chicago as soon as it opens! We spent hours marveling at the incredible collection. It was, in my opinion, the best museum I have ever been to! (Sorry for the art spam, but I’m obviously obsessed!).

After the art institute, we headed to Giordano’s for a late lunch, then did some shopping on Michigan Avenue, with Stan’s Donuts & Coffee in hand. Before heading to the museum, we had checked out of The Drake and into the Palmer House hotel, so we went and dropped off our shopping bags, freshened up, then headed out for a night on the town. We wandered around the lobby to see all of the amazing history of the hotel, then Ubered to the J. Parker rooftop bar for appetizers and drinks.

Day 3: Our final day in the city! We head to open up the Field Museum, which was so, so cool and another amazing learning experience. We were lucky enough to see the Wildlife Photographer of the Year traveling exhibit from London’s Natural History Museum, which was 100% worth it and one of the best museum exhibits I have ever seen. If you ever have the chance to see this exhibit in any museum, we highly recommend!

We head to Cindy’s Rooftop after the Field Museum, where we saw some of the best views of the city while sipping our cocktails. We then wandered down to take our obligatory photos at The Bean, then walked down to the stunning Buckingham Fountain. Keeping up with the theme of getting our steps in, we walked back within the city center and headed to get some much deserved coffee and sweets at Goddess and the Baker before grabbing our bags and heading to the airport.

We also received these recommendations from some local friends that we made on what to do the next time we were in town:

The Signature Lounge at the 96th

DryHop Brewers

Best Intentions

Chicago Magic Lounge

Have you ever been to the Windy City? If so, let me know your recommendations in the comments below.

Love y’all,


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