Breezing through Chicago: What to do in The Windy City

Chicago_Skyline_ImageGrowing up in the Midwest short city getaways would be a choice between Minneapolis, Minnesota or Chicago, Illinois. Although I have been to both cities several times as a child and later as an adult, I reached out to my travel buddy and writer, Jenny Sherman, for some insider tips on the Windy City of Chicago, Illinois.

Enjoy her Breezing through Chicago: What to do in the Windy City!

There are many places to visit in the US, but we think you should place Chicago near the top of your bucket list when deciding where to travel. The city has something for everyone, from those who place shopping and food high on their itinerary, to those people who simply want to find a place of quiet peace and solitude.

In this article, we will give you a taste of what Chicago has to offer you. After reading, we hope we have done enough to convince you to book a flight and a stay at an Airbnb in Chicago, Illinois, because this is one US city you will not regret visiting.

Things to do in Chicago

  • Gaze in awe at the spectacle and beauty of the city. We once mentioned that the secret to life is to look up, and in Chicago, you simply have to! This is the city that invented the skyscraper, and there are over 100 that fill the skyline. From the Art Deco masterpieces of the 1920s to the more modern architectural marvels, you need to put down your smartphones and gaze up at the spectacle above you. But don't strain your neck for too long, as there is more to explore, with both your eyes and your feet. Much of Chicago is made up of beautiful parklands, befitting of the "City in a Garden" that the place is known for, so stroll through the many parks that are listed here. And Chicago is also known as the "City by the Lake," befitting as it is situated alongside Lake Michigan. With walking trails, sandy beaches, and those glorious blue waters, you can spend hours (if not days), exploring Chicago's natural beauty.


  • Grow in knowledge by getting yourself an education. There is something for all tastes if you're looking to grow your mind. Visit one (or more) of the city's museums, from the Prehistoric wonders at The Field Museum to the cultural touchstone that is the Chicago History Museum. Check out the art galleries, including the most prominent of them all, the Art Institute of Chicago, and enjoy the visual feast gifted to us from both classic and modern painters. And explore the multicultural neighbourhoods that make up Chicago, from Chinatown to Greektown, and gain new perspectives by experiencing the different arts and cultures that make up each district.


  • Eat and drink your way through the city. Chicago is famous for its pizzas and hot dogs, so you won't be spoiled for choice if any of those foods take your fancy. But there is so much more to try, so scroll your way through the delicious offerings here, and tempt your taste buds with the many food highlights Chicago has to offer. And if you're prone to the odd tipple or two, know that Chicago's beer scene is huge. Check out the city's many breweries, or enjoy a drink at some of Chicago's diverse range of bars, and spend your days and nights experiencing tastes both new and familiar.


  • And there is so much more. If shopping is your thing, you have to visit The Magnificent Mile, with something for every shopper's taste. For those who love sports, you owe it to yourself to go and see a Major League baseball game. And if you want to get into Chicago's music scene, there are jazz and blues clubs scattered around the city, as well as nightclubs which showcase the best in house music (which originated in the city). And there is so much more. Check out some of the tourist attractions here, as examples. If you are traveling with kids, here are some excellent things to do with kids in Chicago.


Chicago rocks, so when touring the US, you really do need to breeze through this so-called Windy City. Just don't forget to send us a postcard!

**Post contributed by Jenny Sherman, a travel writer from the U.K. based in the Midwest.**

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