Chicago, IL Villa Rentals

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Compare Villas, Resorts, & Rentals in Chicago

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About Chicago Vacation Rentals

There are more than 12877 incredible getaway rentals that are available in Chicago. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chicago.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chicago, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chicago. Places to stay near Chicago are 751.41 ft² on average, with prices averaging AU $513 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chicago. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Chicago, IL


Cook County 4,866 Properties
Chicago 3,727 Properties
Central Chicago 1,494 Properties
Downtown Chicago 1,403 Properties
West Side 767 Properties
The Loop 632 Properties
Near North Side 585 Properties
Lake County 571 Properties
North Side 528 Properties
DuPage County 462 Properties
River North 351 Properties
Near West Side 317 Properties

There are 1981 hotels in Chicago 36 resorts, and 10002 rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago

Frequently Asked Questions About Chicago?

What are the top hotels or resorts in Chicago?

We provide an array of great vacation destinations in Chicago. If you are looking to stay in or around the Chicago area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chicago:

How many hotels, resorts, or rentals are available in Chicago?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 12877 in the Chicago area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chicago. 

Nearby Neighborhood (16)

NeighborhoodProperty Count
Downtown Chicago Rental Villas and Private Getaways in Chicago, Illinois 1403
The Loop Rental Villas and Private Getaways in Chicago, Illinois 632
Near North Side Rental Villas and Private Getaways in Chicago, Illinois 585
River North Rental Villas and Private Getaways in Chicago, Illinois 351
South Loop Rental Villas and Private Getaways in Chicago, Illinois 295
Near South Side Rental Villas and Private Getaways in Chicago, Illinois 276
Lakeview Rental Villas and Private Getaways in Chicago, Illinois 225
West Loop Rental Villas and Private Getaways in Chicago, Illinois 186
Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois 129
Hyde Park Rental Villas and Private Getaways in Chicago, Illinois 72
Edgewater Rental Villas and Private Getaways in Chicago, Illinois 60
Logan Square Rental Villas and Private Getaways in Chicago, Illinois 55
Rogers Park Rental Villas and Private Getaways in Chicago, Illinois 54
Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois 53
O'Hare Rental Villas and Private Getaways in Chicago, Illinois 47
Gold Coast Rental Villas and Private Getaways in Chicago, Illinois 38