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25 Best Things To Do In Chicago

Call it what you will, the Windy City, the City of Big Shoulder, or the Second City, to me Chicago is my home. Chicago is a city that has burned down and was built from ashes. A city that introduced the Ferris Wheel and Farris Bueller. In a city this big, its easy to miss some of the charms and gems Chicago has to offer. As a local, I want to give you an insight into what I love so much. So, lets explore Chi-Town.

1. The Lake Front Trail

Okay, this might be the first time this is the #1 thing to do in Chicago, but trust me, it is and here’s why: Chicago is known for its amazing and iconic architecture and this is the perfect way to get view of the whole city. Take a Divvy (public bikes) or take a walk either North or South of the Loop and I promise, you will fall in love with what you see. Its free, its healthy, and it makes a great cover photo for your Facebook.

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2. Pizza

Yes, pizza. Deep dish really is great here! But so is our thin crust; cut into squares the true Chicago way. I recommend Lou Manlati’s or Art of Pizza for deep dish and Pizano’s or Lou’s for thin.

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3. Go to a game

I am a die-hard Cubs fan so obviously I suggest you go to a Cubs game, plus Wrigley Field is really something to see, but no matter the time of year there is always a sport to watch. We have a team for every major sport so you always have options.

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4. Architecture boat tour

This might actually be my favorite thing to do in the city. The tour takes you down the Chicago River and a (very enthusiastic and knowledgeable) guide gives you a great history of the city and points out all the major buildings in the city. Its perfect for a sunny day with family or friends of any age. Plus, the boat has a full bar.

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5. The Art Institute of Chicago

Since not every day is going to be perfect weather, it’s a good thing Chicago has some of the best museums in the country. In fact, the Art Institute of Chicago was rated the #1 Museum in the U.S. according to TripAdvisor. It offers a range of exhibits and some of the best artwork ever created that even the most novice of viewers would recognize.

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6. Keeping with Museums

I recommend you visit the Chicago History Museum in Lincoln Park. It’s a great museum that walks you through the rich history Chicago has to offer its visitors.

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7. Eat a Chicago style hot dog

Cliché? Sure. Delicious? Hell yes. First off, don’t get one in millennium park. Go to one of Chicago’s many neighborhoods and get one there, like a local. And yes, locals do eat hot dogs.

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8.Lincoln Park Zoo

It’s free; so really you cant go wrong. It’s perfect for a walk through in the summer during the day or night. In the winter the zoo puts out its Zoo Lights, a spectacular light show around the entire zoo. The Zoo also hosts special events for families and evening events for adults (boozy zoo).

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9. Millennium Park

Let me preface and say that I do not think Millennium park alone is the #10 thing to see in Chicago, but what it has to offer puts it up there. Okay, if you have to see the Bean (Could gate) then go on a Monday or Tuesday evening in the Summer. Every Monday and Tuesday in the summer Chicago hosts free movies and concerts in the park. Its open to the public and people are encouraged to bring blankets and a picnic basket, and yes, alcohol is permitted in the park. For a list of these events please visit: even in the winter, Millennium Park offers events and ice-skating for families of all ages.

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10. The Chicago Theater

A great Chicago landmark in the heart of downtown! Enjoy a concert or a comedy show in a cozy, yet elegant, venue. The acoustics are amazing which make it great for shows.

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11. Second City

Tina Fey, Amy Poehler, CHRIS FARLEY, Mike Myers and Bill Murray are just a small handful of the brilliant and talented comedians to come out of Chicago's Second City. Located in Chicago's Old Town, Second City is the home for comedy in the city. Check out a show and have a good laugh.  

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12. Wrigley Field

Go Cubs GOOO, Go Cubs GOOO! Hey Chicago, what do you say? CUBS ARE GONNA WIN TODAY!" Oh, it's a song and a mantra. I am very bias as a true and loyal Cubs fan, but this is a place you have to visit. Baseball fans and people who just appreciate a good time will love Wrigley Field. I recommend doing a tour if you can, this stadium is rich with history.  

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13. Navy Pier

Okay, fine, go. It's the Fisherman's Worf of the Midwest (aside from maybe the Wisconsin Dells), cheesy and a wallet magnet. Yet, I have to admit, there is something special about that Ferris Wheel and getting overdoing it at Harry Cary's. Yes, it is a cliche, but it's not horrible. Navy Pier is home to the Children's Museum, something I loved as a kid, full of things for kids to do. The Pier is also the access point to various boat rides and restaurants perfect for a quick taste of the city. This year Navy Pier re-did the famous Ferris Wheel, and as a Chicagoan and a historian, I kinda want to check it out myself.

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14. The Chicago Athletic Association

Located on Michigan Avenue, this restored men’s club offers fun games, a great hotel, three bars, and great food and views for you to enjoy. Cindy’s rooftop bar is a great way to have a drink and look out on the city with your friends. The CAA hotel is a high end, boutique hotel with loads of history and unique features you wont find anywhere else. The Game Room, located on the second floor, has food and, well, games that are great for an evening. The other restaurant in the CAA is called the Cherry Circle room- its very elegant and I do recommend it but it is pricey. Finally, yes there is more, there is a secret speakeasy located on the second floor between the game room and the sitting room. You can make reservations online at: . the speakeasy is the best part of the hotel, in my opinion. It brings you back to the probation era in both its ambiance and its liquor. I will leave it at that, as I think you should experience the rest for yourself.

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15. The Music Box Theater

This classic Chicago theater is a great way to get out of the bad weather Chicago tends to have. They have special events and showings of classic films every month. In the Christmas season, they have an audience interactive showing of It’s a Wonderful Life- this is my favorite holiday tradition. It’s a great landmark and a fun time.

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