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I literally have lost track of how many times I’ve visited Chicago. I’ve been to Chicago so many times that I was actually beginning to get bored. I know—I couldn’t believe it either! I mean, how can you get bored of one of the most characteristic cities of the United States?? Well, I took on my last two trips to Chicago (within a week of each other) with a different approach—pretend I’d never been to Chicago before! This “tourist-in-your-own-town” mentality (I don’t live in Chicago but may as well for the amount of time I spend there) worked wonders and helped me come up with all sorts of amazing recommendations for you. So, here goes…



M A G N I F I C E N T  M I L E

First of all, I’d definitely suggest staying right in the heart of the city, close to all the most popular attractions. Sheraton Grand Chicago (with a view of the Chicago River and Lake Michigan) is incredible, albeit expensive; my brother @morebrio_ swears by the Millennium Knickerbocker, and I’d say the Hyatt Regency, Fairmont Millennium ParkHoliday Inn Mart Plaza, Kinzie, and Godfrey hotels are all really good options. My favorite method of transportation in Chicago is the Divvy bike share—so I always try to stay in a hotel within biking distance of everything I want to see. Nothing beats shopping on the Magnificent Mile! Except maybe shopping on Champs d’Elysées…check out what I have to say about that in my Paris post!




C H I C A G O  R I V E R

There are a few different ways to enjoy the Chicago River. The easiest is the Chicago Riverwalk—a boardwalk that snakes along the Chicago River with beautiful scenery and great places to eat or indulge in a drink. Another thing you could do is kayak on the river. Renting kayaks is easy and affordable and the view of the city is incredible. My favorite activity is the architecture tour! You can buy tickets for it right on the boardwalk (or online, I’ve always gone with Chicago’s First Lady)—it’s not exactly cheap but it’s so worth it! The tour I always go on is an hour and a half and tours not only the river but Lake Michigan as well. It wouldn’t be summer in Chicago if I wasn’t cruising the waterways of the city on a cool boat with a Summer Shandy in my hand (yes, the boat has a bar)!



N A V Y  P I E R

Of course you need to check out Navy Pier (and ride the ferris wheel!). I like biking from the beach (more on that next) to Navy Pier—it’s not far at all and super fun. There are a lot of restaurants and other cool places to hangout. I highly recommend spending some time there!



L I N C O L N  P A R K  Z O O

It’s free! The zoo is legit, with a lot of cool animals, and completely free! I love going to the Lincoln Park Zoo. Because it’s free.



W I L L I S  T O W E R

Or the Sears Tower—it kind of goes by both names. Whatever you call it, it’s super cool! Did you know it’s actually the second tallest skyscraper in the United States? Yes, taller than the Empire State building and second only to the new One World Trade Center in NYC. Again, not exactly cheap to go up there but the Sky Deck is the perfect Instagram spot.



O A K  S T R E E T  B E A C H

Keep walking down Magnificent Mile and eventually you’ll hit a hidden treasure—Oak Street Beach. Right in the heart of the city, you can bike, play beach volleyball, swim…the works!



B U C K I N G H A M  F O U N T A I N

First of all, the fountain is actually amazing! It’s enormous and on a hot day it’s fun to get cooled off by the fountain’s mist. The area is also cool to walk around—you can see the boats docked at the marina on Lake Michigan and there are some beautiful gardens nearby (not to mention el paletero!).


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Alright, for all the foodies out there here are my top restaurant picks! I love Cuban food—Havana and Paladar definitely make my favorites list. Carnivale takes the cake for delicious food and outrageous ambiance. Del Toro has the best Mexican food. We always choose Lou Malnati’s (specifically the one on State) for Chicago deep dish. Portillo’s has the best Chicago dog. Wildberry is the best breakfast place. I guarantee you’ll find your new favorite restaurant in Chicago!



C L O U D  G A T E

Did you know that’s the Bean’s real name? I didn’t! The Bean is very touristy, I know, but you have to go see it. It’s actually pretty cool because you can see the city skyline reflected in it. It’s also very Chicago! The Bean is located in Millennium Park, too, which is really nice and has a lot of things to do (concerts, ice skating…).


As you can see, my “first-time-tourist” strategy worked! I fell in love with Chicago all over again and found some new surprises along the way. Hope this helps on your next trip to Chicago!


Thanks for reading and keep on flying!

The Adventureist


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