The Ultimate Guide to Chicago

I can’t believe it’s taken me this many years to finally go to Chicago — I am absolutely in love with this city. I’d even consider moving there if the winters weren’t so damn cold. (jk, let’s be real, I’m incapable of leaving NYC). But that being said, I did at least consider it for several seconds which is HUGE. If you are planning a trip to the windy city, here’s a list of things you should add to your itinerary!

1. Architectural Boat Tour

While this may sound like a total snoozefest, let me assure you that it is the exact opposite. I had an incredible time riding down the Chicago River and learning about the history of Chicago and its unique architecture. Taking this boat tour on my first day there really made me appreciate the city during the rest of my stay! This tour was recommended to me by just about everyone, so trust me and just do it! It’ll be totally worth your time.


2. Rooftop Bars:

Chicago’s rooftop bar scene is second only to New York’s. I would be lying if I said I didn’t try to go to every single one. While I didn’t accomplish that mission since I was only there for 4 days, I definitely covered some of the best ones! My favorites are: Cindy’s Rooftop, London House Rooftop, Devereaux, Z Bar, and Streeterville Social. Cindy’s and London House have the best city views. Devereaux is a relatively new bar with a rooftop pool and great views! Z Bar and Streeterville Social have fantastic cocktails. We were even lucky enough to see the Chicago Air Show from some of the rooftops!


3. The Bean

Probably Chicago’s most iconic landmark, Cloud Gate, better known as “the bean” is located in Millennium Park. Take a walk under the arch and make sure to snap a picture for the ‘gram!

4. Deep Dish Pizza

We all know that I went all the way to Chicago JUST for the deep dish pizza, and let me tell you, it did not disappoint. We went to Lou Malnati’s for dinner, and it was the perfect way to cap off a day full of drinking! Pequod’s Pizza, Gino’s East, and Burt’s Place are some other highly recommended pizza places if you’re craving some signature deep dish. Believe me, this pizza is worth every single calorie.

5. Restoration Hardware Cafe

This magnificent furniture store and cafe is literally like your own little slice of heaven. I had to finish up some work one of the days I was in Chicago, so I brought my laptop here and ordered some brunch. I perched up right next to the fountain and had the most relaxing morning I could have asked for. The food was absolutely divine, and the chai was incredible. I ordered the RH Scramble and I’m drooling just thinking about it. This place understandably gets super packed, so remember to make a reservation or get there early!


6. Rent A Private Boat

Y’all, I drove a boat and no one died! (Probably my greatest achievement this summer.) Anyway, I digress. If you’re with a group, I’d definitely recommend renting a boat and driving it down the river yourselves. It’s relaxing and fun, and a great way to see the city. We brought sandwiches and were even able to grill a frozen pizza. There are several different companies you can call, so look up which one works best with your schedule!


7. Shore Club

Shore Club is a lively beach club on North Avenue Beach. Rent a cabana, play some games and drink refreshing cocktails! I obviously had to be extra and grab a drink in this copper pineapple. If you are anything like me, they also have a dope copper flamingo for you to enjoy :)

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8. Brunch at the Fremont

The Fremont is the hot spot for boozy brunch in Chicago. The Fremont offers a buffet brunch, strong bottomless mimosas, and a great ambience! While a bit on the pricier side, if day parties and brunch are your thing — you definitely will not want to miss this.

9. Hampton Social

Hampton Social is known best for its “Rosé all day” sign, amazing seafood (no, I did not have any), and adorable decor. The beach themed venue has hammock swings, a leaf wall with a neon sign, and different rosé every day! Grab yourself a glass and sit on the hammock swing for a relaxing brunch or happy hour.


Other honorable mentions: Three Dots and a Dash is a speakeasy and tropical tiki bar with incredible Polynesian-inspired cocktails. Lost Lake is another tiki bar that was highly recommended to me! Willis Tower and Hancock tower both offer great views of Chicago. Navy Pier is also an amazing place to visit, especially if you’re with family. And definitely check out the Art Institute if you have enough time.

Hope you enjoy your trip to Chicago as much as I enjoyed mine. Feel free to ask me any questions you have on places to stay and where to go, and share your favorite spots with me! xox