1,000+ Rentals in Chicago, IL, USA

The Windy City of Chicago seems to have it all. With beautiful shoreline set along Lake Michigan and sprawling streets filled with everything you'd expect of a major U.S. city, Chicago's distinctive neighborhoods are the perfect spot for a visit.

Chicago boasts nine districts, with 77 neighborhoods offering an eclectic living and touring experience. Whether you thrive on the action of downtown Chicago or prefer something a little less busy, you'll have your fill of galleries, museums, shops, parks, restaurants and more.

• Downtown Loop: Don't hit Chicago without exploring the Loop. Put the iconic Bean in Millennium Park on your list, and swing through the Theater District as well.
• Lakeview: As the name suggests, Lakeview is a thriving lakefront community with a wide array of attractions. Street festivals are popular during the summer, and acres of green space offer breathtaking beauty.
• Humboldt Park: The Spanish Colonial architecture in Humboldt Park helps create a distinctively Latin aura. This is even more evident in the specialty shopping and cuisine.

There are 1,053 vacation rentals available in Chicago across several booking partners.

Rentals in Chicago have a price range between $39 - $2,662. The average price for vacation rentals in Chicago is $122.

Apartments are the top rental type in Chicago, with 482 rentals currently available.