1268+ Rental Villas and Private Getaways in Chicago |
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Chicago Villa Rentals

About Chicago Vacation Rentals

There are more than 1268 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 873.77 ft² on average, with prices averaging US $326 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.

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Top Private Villas, Resorts, and Rentals in Chicago

Type Count
Holiday Apartments 691
Vacation Homes 113
B&B 21
Villas 4

Use these Quick Filters to Find a Vacation Rental in Chicago

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chicago with BedroomVillas.

Weather in Chicago, IL

View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.

December - February
High 15°C       Low -3°C
March - May
High 25°C       Low 4°C
June - August
High 32°C       Low 17°C
September - November
High 28°C       Low 3°C

Stay Near Chicago's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Chicago's Research Top Attractions For Your Vacation


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

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


Chicago 6,882 Properties
Central Chicago 1,671 Properties
Downtown Chicago 1,536 Properties
West Side 822 Properties
The Loop 707 Properties
North Side 650 Properties
Near North Side 607 Properties
Far North Side 382 Properties
Near West Side 379 Properties
South Side 369 Properties
South Loop 369 Properties
Near South Side 356 Properties

Complexes around Chicago, IL


Wells Apartments St Chicago 132 Properties
Town 18 Properties
South Loop Grant Park 29 Properties
Wrigley 35 Properties
Lakeview 20 Properties
Kasa River North 12 Properties
Transit Dt 14 Properties
Naperville Inn 10 Properties
Gold Coast Doorman Blocks 9 Properties
Lofts 14 Properties
Belmont 7 Properties
Mccormick Place 5 Properties
District Block 10 Properties
Sonder South Wabash 10 Properties
Accommodation Schaumburg 5 Properties
See More Complexes

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 vacation rentals have private pools in Chicago?

We have 71 luxury villas and vacation rentals featuriung a private pool in and near Chicago. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Chicago is best for families?

Searching for a family-friendly getaway in Chicago? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

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 1268 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) 
Neighborhood Property Count
Downtown Chicago Rental Villas and Private Getaways in Chicago, Illinois 1536
The Loop Rental Villas and Private Getaways in Chicago, Illinois 707
Near North Side Rental Villas and Private Getaways in Chicago, Illinois 607
South Loop Rental Villas and Private Getaways in Chicago, Illinois 369
Near South Side Rental Villas and Private Getaways in Chicago, Illinois 356
River North Rental Villas and Private Getaways in Chicago, Illinois 320
Lakeview Rental Villas and Private Getaways in Chicago, Illinois 270
West Loop Rental Villas and Private Getaways in Chicago, Illinois 222
Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois 152
Hyde Park Rental Villas and Private Getaways in Chicago, Illinois 104
Logan Square Rental Villas and Private Getaways in Chicago, Illinois 87
Edgewater Rental Villas and Private Getaways in Chicago, Illinois 79
Rogers Park Rental Villas and Private Getaways in Chicago, Illinois 69
O'Hare Rental Villas and Private Getaways in Chicago, Illinois 51
Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois 50
Wicker Park Rental Villas and Private Getaways in Chicago, Illinois 47

People Also Ask

There are 436 hotels in Chicago 1 resorts, and 808 rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago