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

We believe finding a beachfront 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

Beachfront vacation rentals in Chicago

There are 1,899 beachfront rentals near Chicago for all manner or mood of traveling to the shoreline, availability of time off, and size of budget. So, if you are hoping for an affordable Chicago Beach vacation, you can find 10% of the available rentals under $103/night. Or if you are willing to splurge on a luxury vacation in Chicago, there are 190 between $529 and $8,456/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 121 there are short term home and apartment rentals in Chicago near the beach to fit your Illinois vacation needs. The most popular types of beachfront rentals in Chicago are apartments, hotels and houses. Chicago has been a frequently searched travel destination this year and continues to grow in popularity because of its beaches and other water activities. VacationRenter offers a wide selection of available beach vacation rentals 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