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 1,853 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 $61/night. Or if you are willing to splurge on a luxury vacation in Chicago, there are 185 between $597 and $3,075/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 126 there are short term home and apartment rentals in Chicago to fit your Illinois vacation needs. The most popular types of vacation rentals 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,, and many more. Search your travel dates to find available Chicago vacation homes for your trip.

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:
- Beach1,853 vacation rentals
- Condo1,318 vacation rentals
- Apartment1,318 vacation rentals
- Hotel255 vacation rentals
- House233 vacation rentals
- Bed & Breakfast11 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: 369 vacation rentals
- Chicago CityPASS: 363 vacation rentals
- Chicago Riverwalk: 340 vacation rentals
- Buckingham Fountain: 154 vacation rentals