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Best Tours in Chicago: 9 Awesome Ways to See the Windy City in 2017

Hello brew crew!

The Windy City. The City of Big Shoulders. The City in a Garden. With world-renown culture, architecture, parks, lakefront, food and drink, Chicago, the Second City, is second to none. The city is a blast to explore.

While it is easy to see the city on your own, we recommend taking at least one of the several tours to learn about this great metropolis. With expertly trained tour guides, the city and its colorful history will come to life even more.

Below are some of our favorites.

1. Architecture Boat Tours

a large boat in a body of water with a city in the background

Courtesy of Roman Boed

There is a reason this is a “go to” activity for Chicagoans with out of town guests: its awesome. When cruising on the Chicago River and looking at the massive skyscrapers towering above,Daniel Burnham’s famous slogan “Make No Little Plans” slogan rings true. Guides do a great job of weaving in Chicago history with its impressive architecture, giving people an idea of how Chicago formed and developed.

Options Include:

– Chicago Architecture Foundation / Chicago’s First Lady (recommended)

– Shoreline Sightseeing

– Wendella

– Seadog Cruises

2. Food Tours

a group of people eating pizza and drinking a shelf in a store

Bruce cut his teeth leading food tours, and can’t recommend them enough. Why just limit yourself to two senses (sight and hearing) when you can also add in other others (taste, smell, and touch). Chicago is a world renown foodie town with a ton of variety. Food tours will satisfy your yearning to learn more about the city…and your tastebuds as well.

– Chicago Food Planet Food Tours (recommended)

– Chicago Pizza Tours



3. Beer Tours

a group of people posing for a photo


What do we like even more than food? Beer! Similar to food tours yet with an alcoholic twist, you can learn about the city and it’s beer and sinful past while enjoying delicious suds from Chicago’s booming beer scene. We are definitely biased, but our highly rated tours at Chicago Beer Experience combine history and beer in unique, fun ways.

You can choose three different tour options, all each with its unique neighborhoods and themes. Check out more by visiting our website by clicking our link here at Chicago Beer Experience Beer Tours.



4. Segway Tours

a group of people walking down a street


Are they sort of silly? Yes. However, zooming around on these things is actually a lot of fun. You’ll enjoy Chicago’s lakefront and park system by taking a Segway tour. Just don’t fall into Lake Michigan. 😉

Check out:

– City Segway Tours

– Segway Experience of Chicago



5. “Exercise” Tours

a man riding a skateboard up the side of a road


You can work off Chicago’s all of that delicious food and drink you’ve been consuming, including those food and beer tours, by getting some exercise on tours that incorporate physical activities.

We recommend:

– Bobby’s Bike Hike

– Chicago Running Tours

– Urban Kayaks


6. Gangster Tours

a man wearing a hat talking on a cell phone


Chicago’s criminal history is excellent. From the 1800s and the gambling, gansters and brothels, to Prohibition, Capone and Dillinger, there are a lot of tales to tell. While we cover a lot of these stories on our beer tours (beer and criminals seem to have paired together over the years; go figure), there are also some focused tours that you can take.

We recommend:

– The Untouchable Tours

– Chicago Crime Tours


7. Helicopter Tours

a view of a city with tall buildings in the background



One of Chicago’s newer tours will take you on an aerial adventure around the city’s towering skyscrapers and over one of the best skylines in the world.

You can check it out here at Chicago Helicopter Experience.




8. Walking Tours

a group of people standing in front of a building


Looking for a more casual way to see the city? You can simply use your feet and explore much of the area’s architecture and history. While a number of the food and beer tours are walking tours, there are also some “pure play” options as well. Check out:

Inside Chicago Walking Tours

Chicago’s Finest Tours

Chicago Detours

Chicago Elevated

9. Bus Tours

a passenger bus that is parked on the side of a building



Finally, if you really are too tired from all of those beer, food, exercise, and walking tours, you can rest your feet with a bus tour.

We recommend the hop on hop off tours of Chicago Trolley.




We would love to tour with you, and are sure that these other companies would love to have you, too! Regardless, whether visiting Chicago, entertaining out-of-town guests, or just exploring your home, have a blast enjoying the great city of Chicago. We know we do!



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