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Chicago: A guide to short-term rentals

From its world-class museums, one-of-a-kind skyline, all the way to its famed deep dish pizza, everything about Chicago is grand but exceptionally welcoming. Grab a short-term rental and see what the Windy City is all about.

Kasa's short-term rentals in Chicago

Both inside the Loop and out, our short-term rentals in Chicago are near all the things you want them to be near. Restaurants, sports, shopping--you name it, you can walk to it.

Discover Chicago

After booking your short-term rental in Chicago, here's everything you need to know for your trip.

Hugging the southwestern shore of Lake Michigan, Chicago is America’s third most populous city, and the largest in the Midwest, with an estimated population of around 2.7 million. It was first settled in the 1780s by Jean Baptiste Point du Sable, a French-Haitian explorer, but wouldn’t officially become a U.S. city until 1837, after a series of wars and treaties among the United States and the Indigenous tribes that occupied the area. The Chicago Portage, a direct throughway from the Great Lakes to the Mississippi River, made the city an efficient location for trade and transportation.

As manufacturing and finance in Chicago boosted the national economy, congressman Abraham Lincoln was nominated for the Presidency there. In 1871, the Great Chicago Fire decimated about 4 square miles of the city, launching a renewed period of growth, ultimately leading to the building of the world’s first steel-skeleton skyscraper in 1885, a modern marvel then at ten stories tall. As the city expanded, it became America’s foremost rail hub, and U.S. time zones as we know them today were established there as a way to help keep cross-country trains on schedule.

The turn of the century brought immigrants to Chicago from a great many European countries, most notably Germany, Ireland, Poland, and what was formerly Czechoslovakia. In the early 1900s, the Great Migration brought hundreds of thousands of African Americans up from the South, leading to the Chicago Black Renaissance. In the 1960s, the Chicago Freedom Movement, led by Dr. Martin Luther King, Jr., sought to increase fair access for housing, jobs, and education among African Americans.

Today, the city is known for its grand architecture and infrastructure, gorgeous lakefront, first-class museums, and an evolving food scene all just a few blocks from Kasa's short-term rentals. The summers in the city are warm and inviting—-with miles of public beaches to explore-—but it earns its reputation as the Windy City in the winter, when the temperature drops and the cozy factor steps up.