Chicago Villa Rentals
About Chicago Vacation Rentals
There are more than 7645 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 740.46 ft² on average, with prices averaging CA $579 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.
Top Private Villas, Resorts, and Rentals in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 5013 |
| Vacation Homes | 1157 |
| B&B | 50 |
| Villas | 9 |
| Cottages | 5 |
| 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.
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
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
Complexes around Chicago, IL
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:
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55th Floor Penthouse with Award-Winning Views
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- NEW LUXURY PENTHOUSE CONDO
How many vacation rentals have private pools in Chicago?
We have 99 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:
- Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
- ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
- Stay One Chicago
- Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
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.
- NEW LUXURY CONDO WITH PATIO DECK
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Wrigleyville Inn
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 7645 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 | 1486 |
| The Loop Rental Villas and Private Getaways in Chicago, Illinois | 660 |
| Near North Side Rental Villas and Private Getaways in Chicago, Illinois | 640 |
| South Loop Rental Villas and Private Getaways in Chicago, Illinois | 384 |
| Near South Side Rental Villas and Private Getaways in Chicago, Illinois | 369 |
| River North Rental Villas and Private Getaways in Chicago, Illinois | 358 |
| Lakeview Rental Villas and Private Getaways in Chicago, Illinois | 274 |
| West Loop Rental Villas and Private Getaways in Chicago, Illinois | 186 |
| Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois | 167 |
| Hyde Park Rental Villas and Private Getaways in Chicago, Illinois | 101 |
| Logan Square Rental Villas and Private Getaways in Chicago, Illinois | 80 |
| Edgewater Rental Villas and Private Getaways in Chicago, Illinois | 75 |
| Rogers Park Rental Villas and Private Getaways in Chicago, Illinois | 70 |
| Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois | 55 |
| O'Hare Rental Villas and Private Getaways in Chicago, Illinois | 54 |
| Wicker Park Rental Villas and Private Getaways in Chicago, Illinois | 50 |
