Apartment
10.0(418 Reviews)
1 Bedroom
4 Guests
Oceanfront
Parking
Pool
Ocean View
AU $306/Night
7 Nights - AU $2,139
Chicago Villa Rentals
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Compare Villas, Resorts, & Rentals in Chicago
10.0
Apartment
10.0(14 Reviews)
1 Bedroom
2 Guests
Internet
Child Friendly
AU $369/Night
7 Nights - AU $2,581
AU $765/Night
7 Nights - AU $5,354
Apartment
10.0(234 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $365/Night
7 Nights - AU $2,552
AU $300/Night
7 Nights - AU $2,097
Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub- Parking
Balcony/Terrace
Kitchen
AU $660/Night
7 Nights - AU $4,622
Condo
10.0(217 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $424/Night
7 Nights - AU $2,967
Apartment
10.0(176 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
AU $619/Night
7 Nights - AU $4,335
Apartment
10.0(153 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $329/Night
7 Nights - AU $2,302
Luxury Places to Stay in Chicago
Over 8033+ Luxury Places to Stay in or Near Chicago
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
AU $7,167/Night
7 Nights - AU $50,167
New
Apartment
5 Bedrooms
12 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
AU $6,546/Night
7 Nights - AU $45,822
AU $6,219/Night
7 Nights - AU $43,535
Bed & Breakfast
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $6,044/Night
7 Nights - AU $42,310
New
House
12 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $5,972/Night
7 Nights - AU $41,805
House
10.0(39 Reviews)
5 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $5,399/Night
7 Nights - AU $37,793
Apartment
8 Bedrooms
16 Guests
- Parking
View- Air Conditioner
- Internet
AU $5,155/Night
7 Nights - AU $36,084
Apartment
10.0(1 Review)
7 Bedrooms
15 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $5,134/Night
7 Nights - AU $35,938
Apartment
3 Bedrooms
1 Guest
- Hot Tub
- Kitchen
- Internet
Pet Friendly
AU $5,015/Night
7 Nights - AU $35,102
Top-Rated Villas with a Pool in Chicago
Over 1297+ Top-Rated Private Villas with a Pool in or Near Chicago
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $324/Night
7 Nights - AU $2,270
House
10.0(47 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $838/Night
7 Nights - AU $5,863
Apartment
10.0(44 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $276/Night
7 Nights - AU $1,933
Apartment
10.0(15 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $745/Night
7 Nights - AU $5,217
Apartment
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $667/Night
7 Nights - AU $4,668
Apartment
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $671/Night
7 Nights - AU $4,697
Apartment
10.0(9 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $603/Night
7 Nights - AU $4,220
Hotel
10.0(9 Reviews)
- Pool
- Kitchen
- Air Conditioner
- Internet
AU $409/Night
7 Nights - AU $2,862
Apartment
10.0(7 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $2,344/Night
7 Nights - AU $16,408
Pet-Friendly Villas in Chicago
Over 3195+ Pet-Friendly Private Villas in or Near Chicago
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $495/Night
7 Nights - AU $3,467
Apartment
10.0(5 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
AU $692/Night
7 Nights - AU $4,841
Bed & Breakfast
8.0(677 Reviews)
1 Bedroom
- Parking
- Internet
- Pet Friendly
Security/Safety
AU $203/Night
7 Nights - AU $1,422
Apartment
10.0(102 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $251/Night
7 Nights - AU $1,756
Apartment
10.0(5 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
AU $410/Night
7 Nights - AU $2,868
Apartment
10.0(92 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $217/Night
7 Nights - AU $1,522
Apartment
10.0(73 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $344/Night
7 Nights - AU $2,411
Condo
10.0(64 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
Breakfast- Parking
- Ocean View
AU $658/Night
7 Nights - AU $4,608
Apartment
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
AU $562/Night
7 Nights - AU $3,931
Large Private Villas in Chicago
Over 1043+ Large Villas in or Near Chicago for Groups and Families
New
Apartment
9.8(14 Reviews)
2 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
AU $832/Night
7 Nights - AU $5,822
Apartment
10.0(4 Reviews)
6 Bedrooms
20 Guests
Private Beach- EV Charge Station
- Parking
- Ocean View
AU $694/Night
7 Nights - AU $4,855
AU $1,235/Night
7 Nights - AU $8,643
Apartment
9.6(35 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $508/Night
7 Nights - AU $3,559
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
AU $509/Night
7 Nights - AU $3,565
Apartment
9.6(18 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $297/Night
7 Nights - AU $2,077
Villa
9.6(13 Reviews)
1 Bedroom
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $892/Night
7 Nights - AU $6,242
Apartment
9.6(11 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $656/Night
7 Nights - AU $4,589
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $1,129/Night
7 Nights - AU $7,901
Wheelchair Accessible Holiday Homes in Chicago
Over 3069+ Wheelchair Accessible Villas and Holiday Homes in or Near Chicago
Apartment
10.0(61 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $414/Night
7 Nights - AU $2,899
Apartment
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
AU $1,011/Night
7 Nights - AU $7,075
Bed & Breakfast
9.8(217 Reviews)
1 Bedroom
- Breakfast
- Kitchen
- Air Conditioner
- Internet
AU $440/Night
7 Nights - AU $3,079
Apartment
10.0(59 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $385/Night
7 Nights - AU $2,695
House
10.0(1 Review)
1 Bedroom
8 Guests
- View
- Air Conditioner
- Internet
- Pet Friendly
AU $554/Night
7 Nights - AU $3,877
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $534/Night
7 Nights - AU $3,739
Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $597/Night
7 Nights - AU $4,181
Apartment
10.0(11 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $976/Night
7 Nights - AU $6,828
Apartment
10.0(10 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $206/Night
7 Nights - AU $1,445
Chicago Villas, Airbnb and Holiday Homes Under $200
Over 3008+ Chicago Private Villas, Airbnb and Holiday Homes Under $200
Apartment
10.0(64 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $230/Night
7 Nights - AU $1,610
House
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
AU $118/Night
7 Nights - AU $827
AU $158/Night
7 Nights - AU $1,103
Apartment
10.0(58 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $247/Night
7 Nights - AU $1,730
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
AU $266/Night
7 Nights - AU $1,865
Apartment
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
AU $258/Night
7 Nights - AU $1,803
Apartment
10.0(52 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $230/Night
7 Nights - AU $1,610
Apartment
10.0(17 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $252/Night
7 Nights - AU $1,766
New
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $233/Night
7 Nights - AU $1,632
Instantly Bookable Villa Rentals in Chicago
Over 4759+ Instantly Bookable Private Villas in or Near Chicago
Apartment
10.0(123 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $683/Night
7 Nights - AU $4,785
Apartment
10.0(6 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Ocean View
- View
AU $274/Night
7 Nights - AU $1,916
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
AU $359/Night
7 Nights - AU $2,510
Apartment
10.0(87 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $448/Night
7 Nights - AU $3,136
Apartment
10.0(86 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $339/Night
7 Nights - AU $2,376
House
10.0(75 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $703/Night
7 Nights - AU $4,920
Condo
10.0(63 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $302/Night
7 Nights - AU $2,114
Apartment
10.0(62 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $675/Night
7 Nights - AU $4,723
Apartment
10.0(59 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
AU $319/Night
7 Nights - AU $2,237
Book a Last Minute Place to Stay in Chicago
About Chicago Vacation Rentals
There are more than 8042 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 757.78 ft² on average, with prices averaging AU $551 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
There are 925 hotels in Chicago 12 resorts, and 6469 rentals
- Prices for a holiday home in Chicago start at AU $10
- Top rated vacation home in Chicago is 52nd Floor MagMile Penthouse Views Fireplace Pool
- Most popular short term in Chicago is Riu Plaza Chicago
- Cheapest place to stay in Chicago is Homan Square
- Most expensive holiday rental in Chicago is Spacious Luxury 6BR Suite with Jacuzzi and Pool Table
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:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- 1F Chicago's Little italy Graystone nearDowntown
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
How many vacation rentals have private pools in Chicago?
We have 100 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 8042 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 | 1385 |
| The Loop Rental Villas and Private Getaways in Chicago, Illinois | 620 |
| Near North Side Rental Villas and Private Getaways in Chicago, Illinois | 580 |
| River North Rental Villas and Private Getaways in Chicago, Illinois | 345 |
| 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 | 230 |
| West Loop Rental Villas and Private Getaways in Chicago, Illinois | 183 |
| Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois | 127 |
| Hyde Park Rental Villas and Private Getaways in Chicago, Illinois | 76 |
| Edgewater Rental Villas and Private Getaways in Chicago, Illinois | 63 |
| Logan Square Rental Villas and Private Getaways in Chicago, Illinois | 56 |
| Rogers Park Rental Villas and Private Getaways in Chicago, Illinois | 55 |
| Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois | 53 |
| O'Hare Rental Villas and Private Getaways in Chicago, Illinois | 49 |
| Wicker Park Rental Villas and Private Getaways in Chicago, Illinois | 39 |
