6555+ Rental Villas and Private Getaways in Chicago |
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Chicago Villa Rentals

About Chicago Vacation Rentals

There are more than 6555 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 735.01 ft² on average, with prices averaging GB £300 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 4155
Vacation Homes 1048
B&B 49
Villas 8
Cottages 4
Others 3
Cabin Rentals 2

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 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

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 7,244 Properties
Central Chicago 1,955 Properties
Downtown Chicago 1,791 Properties
Near North Side 818 Properties
The Loop 775 Properties
West Side 725 Properties
North Side 571 Properties
River North 484 Properties
South Side 378 Properties
South Loop 372 Properties
Near South Side 360 Properties
Far North Side 353 Properties

Complexes around Chicago, IL


Wells Apartments St Chicago 132 Properties
Town 18 Properties
South Loop Grant Park 29 Properties
Lakeview 17 Properties
Wrigley 30 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
Sonder South Wabash 11 Properties
Accommodation Schaumburg 5 Properties
District Block 10 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 95 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 2025 is over 6555 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 1791
Near North Side Rental Villas and Private Getaways in Chicago, Illinois 818
The Loop Rental Villas and Private Getaways in Chicago, Illinois 775
River North Rental Villas and Private Getaways in Chicago, Illinois 484
South Loop Rental Villas and Private Getaways in Chicago, Illinois 372
Near South Side Rental Villas and Private Getaways in Chicago, Illinois 360
Lakeview Rental Villas and Private Getaways in Chicago, Illinois 236
West Loop Rental Villas and Private Getaways in Chicago, Illinois 198
Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois 143
Hyde Park Rental Villas and Private Getaways in Chicago, Illinois 84
Logan Square Rental Villas and Private Getaways in Chicago, Illinois 78
Rogers Park Rental Villas and Private Getaways in Chicago, Illinois 67
O'Hare Rental Villas and Private Getaways in Chicago, Illinois 66
Edgewater Rental Villas and Private Getaways in Chicago, Illinois 55
Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois 45
Wicker Park Rental Villas and Private Getaways in Chicago, Illinois 40

People Also Ask

There are 743 hotels in Chicago 33 resorts, and 5213 rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago