The Windy City Top 10: Great Things to do in Chicago

The Windy City, Chicago, Ill., is enormous, and can be overwhelming to first-time visitors. Here is a list of 10 great things to do when you visit Chicago, in no particular order. 
Navy Pier in Chicago. Photo by Charish Badzinski.

Navy Pier. 
With its carnival-like atmosphere, breathtaking views of the city–particularly at night, live music, boardwalk bars and kitschy tourist shops, you simply gotta go. Shuttles from downtown make it easy to bypass the parking mess you might otherwise encounter. Take a boat ride, if the mood strikes you, or just stroll the pier and enjoy the food, the ferris wheel and the people watching. FREE.


Chicago blues at Kingston Mines. 
Get a taste of Chicago blues in a place that seemingly never sleeps. In actuality, on weekends, Kingston Mines stays open until about 4 or 5 a.m. The club has two stages in two different rooms, and performers switch back and forth throughout the night, so the audience enjoys music that almost never stops. Grab a seat quickly, or you might end up dancing through the next set! Food is served late, the drink prices are a welcome relief from the Michigan Avenue mark up. Club entry: $20, with significant discounts for students and military.

Kingston Mines Website


Millennium Park.
At Millennium Park, you’ll find an amalgam of art, architecture, park space, performance venue and splashing pools, all in the heart of the city. From Cloud Gate, the giant reflective bean, to the eerie screens with faces in Crown Fountain to the impressive amphitheater, a sunny afternoon spent here, will be well spent. 

The big silver bean, known as Cloud Gate, at Millennium Park in Chicago.
Photo by Charish Badzinski.

Art Institute of Chicago. When it comes to museums, sometimes it’s best to save the experience for a cold, cloudy or rainy day–and Chicago has its share. After all, it’s a safe bet they’ll still be there the next time you visit the city. But if you’re up for art, the Art Institute of Chicago is a great place to visit. You’ll see original paintings by the big wigs of impressionism, like Monet; cubism, like Picasso, and so much more. Adults $18.

Crown Fountain in Chicago. The ever-changing faces are strangely creepy,
but it’s a fun place to splash around on a hot day. Photo by Charish Badzinski.

The Second City. 
This is an improv theatre that has been a training ground for Saturday Night Live and other comedic greats, like John Belushi, Dan Aykroyd, George Wendt, Amy Sedaris and Tina Fey. Check out The Second City alumni list. Of course the alumni are important, but keep in mind when you go to The Second City, you may see the next big thing. Shows do sell out, so buy tickets in advance. Some shows have an extra dose of improv with audience involvement–it’s good fun watching the actors hone their craft, especially when you’re feeding them content from the cheap seats. Ticket prices vary.

Even the view from the ladies room is impressive. It’s located one floor above 
The Signature Room dining area in the John Hancock building, Chicago.
Photo by Nora Aune.

Brunch at The Signature Room. 
Enjoy an elegant brunch on the 95th floor of the John Hancock Center. These days the restaurant offers an extended appetizer and desert buffet with a  selection of entrees made to order, including leg of lamb, crab cakes, steak and eggs, Alaskan Halibut and lemon ricotta pancakes. The view alone is priceless, so it’s worth the splurge. And, you can save the $15 you’d spend on a visit to the Sears Tower Skydeck, because this view is superior and the lines are nearly non-existent. Make reservations in advance at (312) 787-9596. Brunch is served Sundays 10 a.m. – 2 p.m. $45 per person. 

Enjoying brunch at the elegant Signature Room in the John Hancock
building, Chicago. Photo by Nora Aune.

Michigan Avenue. 
They call it The Magnificent Mile for a reason; it’ll be a miracle if you don’t walk around slack-jawed and drooling. The elegant boulevard, the flowerbeds, the occasional outdoor art displays and the access to high end fashion and cuisine make this a must see in Chicago. Seek out Vosges chocolates. You’ll thank me. FREE, unless you shop! 

Chicago’s Buckingham Fountain. Not on this list, but worth a peek!
Photo by Charish Badzinski.

Gino’s East Pizza.
You want awesome Chicago deep dish and a pitcher? Be prepared to wait for it! Nestle in to a marked-up booth at Gino’s East and come prepared to blissfully wait for an hour or so for your pie. Bring markers, pens or white correction fluid; most locations allow you to leave your grafitti on their walls, tables, light fixtures…you name it. Seek out the nearest location to you, and be prepared to stand in line behind other hungry pizza lovers. Between the wait for the pie and the wait in line, this is a time commitment, but one that’s worth it.

Pizza, with a side of graffiti, at Chicago’s Gino’s East.
Photo by Nora Aune. 

Chicago Dog. 
Mustard, onion, relish, peppers, celery salt, tomatoes and dill pickle on a sesame seed bun with a delicious dog tucked in the middle. Line ’em up, knock ’em down. Get one. Just find a place. They’re pretty awesome. Prices vary.

Sears Tower Skydeck. 
If you have brunch at The Signature Room, this may be somewhat redundant. But you can get a taste of Chicago history and some excellent views from the Skydeck, in the Sears Tower, the tallest building in the western hemisphere. There are often lines, but if you’ve never seen it, and it’s a must-do on your list, just be patient. Your moment will come, and once you’re on the Skydeck, you can linger as long as you like. Be sure to check out the toe-tingling plexi platform. Adults $15. 


There’s much more to see and do in Chicago, which goes without saying. What are your favorite Chicago sites and activities? 

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Charish Badzinski is an explorer, foodie and award-winning travel and food writer. When she isn’t working to build her blog: Rollerbag Goddess Rolls the World, she applies her worldview to her small business, providing strategic communications, media relations and writing support to individuals and organizations. 

Find Charish on Twitter: @charishb
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Creative Commons License
Rollerbag Goddess Rolls the World by Charish Badzinski is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License.
Based on a work at rollerbaggoddess.blogspot.com.
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