The best things to do in Shy Town
The windy city is jam-packed with fun things to do and experience.
Chicago, otherwise known as Shy Town or the Windy City, is the most populous midwestern metropolis in the state of Illinois. It’s famous for food, culture, and sports teams, but there’s so much more to the big city than meets the eye.
There is no shortage of exciting and memorable experiences to be had. We’ve compiled a list of the best of the best when it comes to traveling to Chicago so you can do it right without all the research.
Race a turtle for your chance to win big
You read that right. At Big Joe’s, a local downtown dive bar, you can take part in some interesting animal races. Turtle Racing at Big Joe’s kind of takes the cake.
— Alex Koppel (@arsduo) March 12, 2016
It’s located in Lincoln Square and has all your regular pub fare and drinks to choose from, but picking your own turtle and betting on the little guy is what you’ll remember from your visit to the dive bar. No turtles are harmed at Big Joe’s because they are more than racers—they’re family.
Stretch your stomach at a food challenge
The food in Chicago is just one of its main draws, but the food challenges in the city are on a whole different level altogether. So many restaurants offer different challenges with different rewards that it’s hard to choose just one but your stomach may not be able to handle them all.
At Cheesie’s you can try your hand at a gigantic eight-pound grilled cheese to win gift certificates or you can head over to Rudy’s Bar and Grille if you’ve got a hankering for over five pounds of food, including a hamburger and all the regular sides. If you complete the Rudy’s challenge, you get a free t-shirt.
See one of the many iconic landmarks
Another great thing to do in Chicago is to hit up all the places that make the city stand out from the crowd. At Cloud Gate, you’ll find the famous ‘bean’, a piece of reflective mirror art that takes the landscape of the city and distorts it into a beautiful panoramic view.
Other must-see landmarks include the Skydeck at Willis Tower, where you can get a view of the whole city, and Wrigley Field, the now-famous baseball field. Even if you’re not a sports fan, it’s not to be missed.
Hit up the Red Light District
Want something a little seedier and backdoor-ish? Chicago’s Red Light District is the place for you. The district offers a look into the darker history of the city and gives visitors a less-touristy version of Chicago. There are tours you can join like the adults-only bus tour to help guide you on your visit.
The Sinner, Victims & Vice: Red Light District Pub Crawl is also a part of the Red Light District experience, so if nightlife is up your alley, the pub crawl is for you.
Immerse yourself in the culture at a museum or gallery
It doesn’t matter what kind of educational or cultural experience you’re looking for when you hit up Chicago, because it has something for pretty much everyone. The city has a good number of different galleries and museums to choose from such as the Art Institute of Chicago or the Museum of Science and Industry.
When it comes to downtown Chicago attractions, the American Writers Museum is one of the best. You can explore the different lives of classic literature writers and there’s even a kid station if you happen to be on a family trip.
Check the local music scene
There aren’t many places in the U.S. that rival Chicago’s music scene. The city has become a major center for live music and has over a hundred places to catch a local band, no matter your style. Blues, house, and even EDM is said to have originated in Chicago.
Of course, if you’re planning your trip in the summer, you could always hit up Lollapalooza, the famous four-day festival that takes over Grant Park every year.
The 2020 line-up is yet to be released, but it’s no doubt going to be a stunner just like every other year.
Beat light pollution at Adler Planetarium
The Adler Planetarium is a perfect combination of museum and planetarium so you’ll get a lot of bang for your buck when you visit this popular Chicago destination. It’s located within close proximity to the aquarium, too, so you will be within walking distance of another Chicago hotspot.
At the planetarium, you will get unobstructed views of the sky and plenty of shows and exhibits to choose from such as the Universe: A Walk Through Space and Time where you’ll learn everything there is to know about the universe or you can even get a yoga workout in with their Sun Salutations Yoga class under a blanket of stars and planets.
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