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

We believe finding a condo 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

Condo vacation rentals in Chicago

There are 1,899 beachfront 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 condo in Chicago, you can find 10% of the condos available for under $103/night. Or if you are eager and able to splurge on a luxury vacation in Chicago, there are 190 condos for rent between $529 and $8,456/night. Whether you are traveling by yourself, with a significant other, or a family of five, there are available condos for rent to make your Illinois vacation a great experience which is completely in your control. Your Chicago vacation should be as relaxing as possible, it’s vacation after all. When you are in a condo, you have the opportunity to make this vacation dream a reality. Most of the condos for rent in Chicago have a full size kitchen so that meal time is more customized and at your own speed. An additional bonus of booking a condo in Chicago for your vacation is the availablity of washers and dryers in unit; a major plus when packing light.

Chicago has been a frequently searched travel destination this year and continues to grow in popularity for its number of available condo properties. VacationRenter offers a wide selection of available beach vacation rentasl 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 beach 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.

More 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:
- Beach1,899 vacation rentals
- Condo1,312 vacation rentals
- Apartment1,312 vacation rentals
- Hotel321 vacation rentals
- House236 vacation rentals
- Bed & Breakfast14 vacation rentals
- Private Room10 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: 435 vacation rentals
- Chicago Riverwalk: 381 vacation rentals
- Chicago CityPASS: 380 vacation rentals
- Buckingham Fountain: 189 vacation rentals