Top 5 Places to Go and Things to Do in Chicago

So, you’re attending the 2018 TESOL Convention in Chicago. Congratulations! You’ll be visiting the finest city on earth. That is a completely unbiased, verifiable fact, straight from someone who only spent a measly two decades growing up and living in Chicagoland. Alright, so I might be slightly biased, but I do still think of Chicago as “home” and have had the pleasure of enjoying most of the city’s sights, sounds—and deep-dish pizza. Being one of two resident Chicago experts here at TESOL, I wanted to share some of what I think are the best places to see and things to do in Chicago (when you aren’t listening to me speak at the convention, obviously). So without further delay, I’m sharing my top 5 with you. I wanted to list 10, but our cranky blog editor thought that would be too much. The joke’s on him, though, since I may have squeezed in a 6th after he edited this—you’ll just have to read on to find out . . .

1. Willis Tower Sears Tower

Let’s get this one out of the way. Ask a local for directions to the Willis Tower and you’ll get an eye-roll first and directions second. Formerly the world’s tallest building, and originally named the Sears Tower (the preferred name by most Chicagoans), this is one of the most popular attractions in the city and is currently the second tallest building in the United States. The observation deck boasts an enclosed glass ledge that hangs off the side of the building, so when you look down, all you see in the street below. Maybe a visit to the top of this 110 story building isn’t for those with a fear of heights, but on a clear day you can see across the entire city and even as far as the shoreline of Michigan.

Local tip: If you don’t want to pay to look out of a window, grab a drink or small plate at the Signature Room in the Hancock Building, the city’s fourth tallest building, which still offers great views. Reservation are strongly recommended.

2. Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium, Museum of Science and Industry)

Ah yes – Staples in the field trip repertoire for every Chicagoland school, these world-renowned institutions are also walking distance from McCormick Place; so when you’re done hearing everything I have to say about U.S. policies impacting English learners, you can check out some beluga whales, gaze at the galaxy, stand next to the world’s most complete Tyrannosaurs Rex skeleton, or board an actual German U-Boat that was captured during World War II.

Local tip: Students and educators usually receive an on-site discount if they show their ID at many of these museums, so be sure to bring yours! If you plan to visit more than one or two, I would also look into a CityPass, which will give you discounted admission to many attractions for one price.

3. The Magnificent Mile

You might want to leave your credit card at home if you’re a shopaholic and plan to visit the Mag Mile, which is a stretch of Michigan Avenue on the city’s Near Northside. Filled with flagship stores from the world’s top retailers and historic landmark hotels, the Mag Mile also boasts some of the city’s greatest architectural wonders, such as the Tribune Building, Hancock Building, Wrigley Building, and the Chicago Water Tower, which is one of the only structures to survive the Great Chicago Fire of 1871.

Local tip: After lots of walking, be sure to stop off at Water Tower Place to get a meal or drink at Harry Caray’s 7th Inning Stretch and then check out the Chicago Sports Museum next door.

4. Wrigley Field and Wrigleyville

When convention starts, the city will be abuzz with optimism for the BEST baseball team on earth, the World Champion Chicago Cubs. Yeah, you read that right. After 108 years of misery for fans across the city, including me and several generations of my family, the Cubbies won it all in 2016 and are contenders for another title in 2018. Lucky for you, the season begins with an away series in Miami, so tours of historic Wrigley Field, the country’s second oldest professional ballpark, are available to the public once the season starts. Known around the world for its classic features, such as its hand-operated scoreboard and ivy-covered brick outfield wall, you won’t want to miss out on visiting this Chicago and national landmark.

Local tip: Outside of Wrigley Field can be just as fun as inside of the ballpark. Wrigleyville, the neighborhood that surrounds the park, is a great place to watch the game (it will be VERY busy on 29 March, the season’s first day). Regardless of when you go, Sluggers and Murphy’s Bleachers will offer you great atmosphere to watch a Cubs game.

5. Navy Pier

One of the city’s most recognizable attractions is the 101 year old Navy Pier, a collection of shopping, dining, entertainment, and museum venues. Here you will find the popular Centennial Wheel, which takes you over 200 feet in the air and offers 360-degree views of Lake Michigan and the Chicago skyline. Too cold for a Ferris wheel? Not to worry, the gondolas are enclosed to help shield you from the always unpredictable Chicago weather. If you’re traveling to Chicago with your kids, the Chicago Children’s Museum is located at Navy Pier and is a great hands-on museum that kids of all ages will be sure to love!

Local tip: Navy Pier is a great place to begin a lake or river cruise. Get great views of the Chicago skyline off the coast of Lake Michigan, and get up-close-and-personal with some of Chicago’s most beautiful architecture while you cruise down the Chicago River.

6. BONUS: The Second City

In a show of true Midwestern hospitality, I’ll give you one more. Couldn’t score tickets to see Hamilton? That’s okay! Some of the best shows not featuring a pistol duel in Chicago are at The Second City. With alumni that include Dan Aykroyd, Bill Murray, Amy Poehler, and Keegan-Michael Key (and many more), shows here feature some of the best improv comedy in the world. Be sure to get your tickets fast because many shows tend to sell out.

Local tip: If you can’t get tickets for a show but want a taste of the celebrated Chicago comedy scene, Zanies is right around the corner from The Second City and has featured some of the most famous stand-up comics in history.

David Cutler with Peacock

“I’m gonna be the first guy to ride a peacock—giddy-up!

Author Bio

David Cutler is the policy and communications manager at TESOL International Association. He received his bachelor’s in social studies education from Ithaca College and his master’s degree in public administration from Cornell University. His work at TESOL includes monitoring and responding to policies that impact English language teachers and learners, organizing the annual TESOL Advocacy & Policy Summit, and managing the association’s communications initiatives. Outside of work, his interests include the Chicago Cubs, binge watching Full House, and traveling with his wife Lindsay. Be sure to follow David on Twitter.

Note: Never let the “cranky blog editor” caption your author photo.

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2 Responses to Top 5 Places to Go and Things to Do in Chicago

  1. Barbara Wookey says:

    I am looking forward to Chicago TESOL, and I appreciate receiving your 5 top things to do and see. I’ll be checking them out. Just wanting to know what are your new 5 recommendations?
    See you there!
    Barbara Wookey