Chicago: Things To Do in the Windy City

Chicago Skyline

As Frank Sinatra sang it, “Chicago is my Kind of Town.” Chicago is known as “the windy city.” Sitting on the southern tip of Lake Michigan, it can be a little windy and also a whole lot of fun. In this Chicago Travel Guide, come along as I share some of my favourite places to visit while in Chicago. Hold onto your hat. Let’s explore the diversity and beauty Chicago has to offer.

Chicago Waterfront

Willis Tower

Willis Tower on Chicago's waterfront
Willis Tower

The first city to build skyscrapers in 1885, the city of Chicago certainly continues in that tradition. Buildings that have over 100 floors can be seen along Chicago’s waterfront. For a real thrill, you can go to Willis Tower and stand on the glass floor on the 103rd floor. Take in the beauty of the city from above, right under your feet. There is a fee to do that, but if you just want to get a good view and a good drink, go to the 95th floor and stop in at the Signature Lounge. Sit, have a drink and take in the beautiful view of Chicago. A great time with a great view.

Adler Planetarium

Adler Planetarium

Adler Planetarium on Chicago’s waterfront is America’s first Planetarium. An interesting and interactive peek at the world among the stars. As you walk inside the big double doors, a whole new universe lays out before you. Touch a meteorite or see a show in the domed theatre. Planets hang from the ceiling as you walk through the museum and you travel through space. Exhibits of planet rovers such as the Mars Rover Perseverance and make a meteorite hit the earth with such force it will make you jump.

I so enjoyed my time at the Adler Planetarium. Check out my visit when I Roadtripped to the USA. Adler Planetarium will give you an exciting trip through space. It is a must-see when visiting Chicago.

Chicago River Walk

Adler Planetarium Chicago travel guide
Shops on the Chicago River                           *photo credit John Benitez

The best way to drink in the rich culture of Chicago is to take a walk along the Chicago River Walk. The walk offers great restaurants like the Chicago Brewhouse and interesting museums like the McCormick Bridgehouse, as well as events on the river itself. The Chicago Duck Derby is a fundraiser for Special Olympics where they dump 60,000 little yellow rubber ducks into the river, and you can watch them race to the finish line. If you happen to be in the area around St. Patrick’s Day, you can enjoy a wonderful parade and watch as they turn the Chicago River green. Whatever time you go, make sure you check out their special events calendar.

Navy Pier

Ferris Wheel on Navy Pier                             *photo credit Gabrel Tovar

Navy Pier is a great place to go for both a breathtaking view of Lake Michigan but also for its fair-type atmosphere. Stroll down the pier and take a ride on the Centennial Ferris Wheel and get a 360-degree view of Chicago and Lake Michigan. Ride the carousel or swing on the Wave Swinger. Play a game like Chicago’s Time Freak Game or get through the Maze and Chicago’s Funhouse Maze. A fun afternoon on the pier is not complete without a falafel or some Gelato that is offered along the pier. At the end of the evening stand on the pier and watch the sunset over Lake Michigan. You are guaranteed a fun-filled day at Chicago’s Navy Pier.

Free and Fun in Chicago

Oz Park

I love fun and unusual, and if it is free, all the better. A trip to the land of Oz is just around the corner. The author of The Wonderful Wizard of Oz, Frank Baim, settled in Chicago in 1891. At Oz Park, you can take a trip down the yellow brook road to Dorthy’s Playlot, where the kids can play and run or stroll through the emerald garden among the beautiful flowers. All the while greeting statues of the characters we have all grown to love as you walk through the park.

Chicago Cultural Center

Chicago Cultural Center is also a great place to visit, and entrance is free. See the world’s largest Tiffany Glass Dome while taking in the spectacular architecture of this historic building. Shop local artisans that showcase and sell their art in the Buddy space. Take in an art exhibit or listen to a live concert. Make sure you check out their events calendar for the many concerts and events held in this spectacular 1897 building.

Lincoln Park Zoo

A trip to the zoo is always a fun time, no matter how old you are. Since its conception in 1868, Lincoln Park Zoo has been inspiring the love of animals and teaching its visitors about the diversity nature has to offer for free. It is the only privately managed free zoo in the country and well worth the visit. Spend the day with the animals. You will love it.

Food and Sports

Baseball at Wrigley Field


I am and have always been a big baseball fan. If I am in a city and the opportunity arises, I will go to a baseball game. The chances in Chicago are higher since they have two teams, the Sox and the Cubs. Wrigley Field is one of the oldest baseball fields still left. Its iconic ivy wall covering the outfield walls is famous.

On one trip to Wrigley Field, I happened to be chatting with the security guard and mentioned I was from Canada and was thrilled to be in Wrigley Field and see the ivy wall. He asked if I wanted to see it up close, but we would have to keep it our little secret as it was not really allowed. As I crept out onto the empty field, the wall was just a few steps away. I turned my back against the ivy, stepped back into the wall, and disappeared. It was an experience I will never forget standing in the ivy of Wrigley’s field.

While you’re at the baseball park, do not forget to try a Chicago Dog. You will be so glad you did.

Pizzeria Uno

Chicago is a sports town, and where there are sports, there is food. Most famous is their Chicago Deep Dish Pizza. Truly, where the word pie comes from in “pizza pie.” Pizzeria Uno is the first restaurant to make deep-dish pizza in Chicago. Opening in 1943, they are still in operation today in Chicago’s River North Neighborhood. Experience the original deep-dish pizza. Make sure you bring a fork and a good appetite, you will need it.


Chicago is not only known for its deep-dish pizza but also for its hotdogs. The best place to get authentic Chicago hotdogs is Portello’s. Started in 1963 by Dick Portillo, “The Dog House” was a small trailer and a man with a dream. By 1967, they had moved into their first building, and they have been serving the best hotdogs and sandwiches you can find in Chicago ever since. Try their Italian beef sandwiches and top it off with a chocolate cake shake. A trip to Chicago is not complete without a trip to Portillo’s.

Chicago has all different flavours of both food and attractions. From the beautiful Skyline to the best food in the Midwest. Chicago is a travel destination you will want to go to back to again and again.

Do you have a favourite place to visit when in Chicago? Let me know in the comments.

Thanks for coming along on my Chipmunk Adventure. Enjoy your time in the Windy City! See you next week.


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