Chicago is known as the windy city. Sitting on the southern tip of Lake Michigan can be a little windy and also a whole lot of fun. Hold onto your hat, let’s explore the diversity and beauty Chicago has to offer. 

Let’s go Downtown

Willis Tower

The first city to build skyscrapers in 1885 the city continues to not disappoint. Buildings that have over 100 floors can be seen along Chicago’s downtown. 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. A great time with a great view. 

Willis Tower stands tall over Chi-Town

Chicago River Walk

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 right on the river itself. The Chicago Duck Derby. 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 turning of the Chicago River green. Whatever time you go make sure you check out their special events calendar. 

A meander along the Chicago Riverwalk is the perfect way to spend an afternoon.

Navy Pier

Navy Pier is a great place to go for both a breathtaking view of Lake Michigan but also for a fair-type atmosphere. Take a ride on the Centennial Ferris Wheel and get a 360-degree view of Chicago and Lake Michigan. Don’t forget to grab a falafel or some Gelato to make your afternoon complete. 


Free and Interesting

Oz Park

I love interesting 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 which are laid out all through the park. 

Chicago Culture Center

Chicago Cultural Center is also a great place to visit and entrance is free. See the world’s largest Tiffany Glass Dome as well as make sure you check out their events calendar for the many concerts ad events held in this spectacular 1897 building. 

Wander the Chicago Cultural Center

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. 

Lincoln Park Zoo is a great (and free!) way to experience some of the planet’s most fascinating animals.

Food and Sports

Pizzeria Uno

Chicago is a sports town and where there are sports there is food. Most famous is their Chicago Deep Dish Pizza. Truly from 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. 


I am and have always been a big baseball fan. If I am in a city and the opportunity rises I will go to a baseball game. The chances in Chicago are higher since they have 2 teams, the White 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 and 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. 

There’s no place more iconic in American baseball than Wrigley Field.

While your in Chicago, carve out some time to experience the city’s bestceer scene! Here are the Best Breweries in Chicago.