The best rentals from the top sites, all in one place

We believe finding a vacation rental in Chicago should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Chicago

Vacation rentals in Chicago

There are 1,876 vacation rentals near Chicago for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Chicago vacation, you can find 10% rentals under $106/night. Or if you are willing to splurge on a luxury vacation in Chicago, there are 188 between $549 and $3,399/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 120 there are short term home and apartment rentals in Chicago to fit your Illinois vacation needs. The most popular types of short-term rental homes in Chicago are apartments, hotels and houses. Chicago has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway, Booking.com, and many more. Search your travel dates to find available Chicago vacation homes for your trip.

Where is Chicago

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.

Quick Guide to Chicago

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 offers 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.

Home-types in Chicago

Chicago has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Chicago:
- Beach1,876 vacation rentals
- Condo1,300 vacation rentals
- Apartment1,300 vacation rentals
- Hotel295 vacation rentals
- House236 vacation rentals
- Bed & Breakfast14 vacation rentals

Points of interests in Chicago

Chicago has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Chicago:
- Chicago Cultural Center: 405 vacation rentals
- Chicago CityPASS: 380 vacation rentals
- Chicago Riverwalk: 349 vacation rentals
- Buckingham Fountain: 171 vacation rentals