Apartment
8.4(11 Reviews)
1 Bedroom
2 Guests
Kitchen
Air Conditioner
Internet
Pet Friendly
US $192/Night
7 Nights - US $1,343
Chicago, IL Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
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Compare Villas, Resorts, & Rentals in Chicago
8.4
Apartment
10.0(14 Reviews)
1 Bedroom
2 Guests
- Internet
Child Friendly
Security/Safety
US $256/Night
7 Nights - US $1,792
Unlock the Best Price
Apartment
10.0(420 Reviews)
1 Bedroom
4 Guests
Parking
Pool
Ocean View
View
US $236/Night
7 Nights - US $1,649
US $162/Night
7 Nights - US $1,136
Apartment
10.0(378 Reviews)
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $228/Night
7 Nights - US $1,594
Apartment
10.0(318 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- View
- Kitchen
US $275/Night
7 Nights - US $1,926
Apartment
10.0(317 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
Balcony/Terrace
US $877/Night
7 Nights - US $6,139
Apartment
10.0(269 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $320/Night
7 Nights - US $2,241
Luxury Holiday Rentals in Chicago
Over 8193+ Luxury Holiday Rentals in or Near Chicago
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $4,976/Night
7 Nights - US $34,831
New
Apartment
5 Bedrooms
12 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Kitchen
US $4,545/Night
7 Nights - US $31,814
US $4,435/Night
7 Nights - US $31,044
Bed & Breakfast
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,227/Night
7 Nights - US $29,591
Apartment
9 Bedrooms
25 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $3,941/Night
7 Nights - US $27,585
House
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,672/Night
7 Nights - US $25,705
Apartment
8 Bedrooms
16 Guests
- Parking
- View
- Air Conditioner
- Internet
US $3,579/Night
7 Nights - US $25,053
New
Apartment
3 Bedrooms
1 Guest
Hot Tub- Kitchen
- Internet
- Pet Friendly
US $3,482/Night
7 Nights - US $24,371
House
6 Bedrooms
26 Guests
Private Beach- EV Charge Station
- Parking
- Ocean View
US $3,466/Night
7 Nights - US $24,260
Top-Rated Holiday Rentals with a Pool in Chicago
Over 1295+ The Best Private Villas and Holiday Rentals in Chicago with a Pool
Apartment
10.0(252 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $245/Night
7 Nights - US $1,718
Apartment
10.0(235 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $196/Night
7 Nights - US $1,374
Apartment
10.0(219 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $455/Night
7 Nights - US $3,187
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $215/Night
7 Nights - US $1,503
House
10.0(48 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $620/Night
7 Nights - US $4,343
Apartment
10.0(46 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $182/Night
7 Nights - US $1,275
Apartment
10.0(15 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $466/Night
7 Nights - US $3,265
Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $507/Night
7 Nights - US $3,548
Apartment
10.0(11 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $560/Night
7 Nights - US $3,917
Pet-Friendly Holiday Rentals in Chicago
Over 3318+ Pet-Friendly Holiday Rentals in or Near Chicago
Condo
10.0(234 Reviews)
2 Bedrooms
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $415/Night
7 Nights - US $2,907
Apartment
10.0(5 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $318/Night
7 Nights - US $2,228
Bed & Breakfast
8.2(687 Reviews)
1 Bedroom
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $143/Night
7 Nights - US $998
Condo
10.0(222 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $281/Night
7 Nights - US $1,969
Apartment
10.0(4 Reviews)
6 Bedrooms
20 Guests
- Private Beach
- EV Charge Station
- Parking
- Ocean View
US $482/Night
7 Nights - US $3,371
Apartment
10.0(141 Reviews)
3 Bedrooms
10 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $183/Night
7 Nights - US $1,283
Condo
10.0(140 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $499/Night
7 Nights - US $3,490
Apartment
10.0(105 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $196/Night
7 Nights - US $1,372
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $353/Night
7 Nights - US $2,473
Large Holiday Rentals and Private Villas in Chicago
Over 1067+ Large Holiday Rentals and Private Villas in or Near Chicago
House
10.0(152 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,099/Night
7 Nights - US $7,696
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $345/Night
7 Nights - US $2,417
US $507/Night
7 Nights - US $3,551
Apartment
10.0(126 Reviews)
4 Bedrooms
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $740/Night
7 Nights - US $5,182
House
10.0(3 Reviews)
5 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $2,234/Night
7 Nights - US $15,637
Apartment
10.0(120 Reviews)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $731/Night
7 Nights - US $5,119
House
10.0(93 Reviews)
7 Bedrooms
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $905/Night
7 Nights - US $6,335
House
10.0(71 Reviews)
5 Bedrooms
12 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $1,961/Night
7 Nights - US $13,725
Apartment
10.0(71 Reviews)
5 Bedrooms
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,142/Night
7 Nights - US $7,992
Wheelchair Accessible Holiday Homes in Chicago
Over 3060+ Wheelchair Accessible Holiday Homes in or Near Chicago
Apartment
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $282/Night
7 Nights - US $1,974
Apartment
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $470/Night
7 Nights - US $3,287
Bed & Breakfast
9.8(219 Reviews)
1 Bedroom
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,006
Apartment
10.0(60 Reviews)
1 Bedroom
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $185/Night
7 Nights - US $1,298
House
10.0(2 Reviews)
1 Bedroom
8 Guests
- View
- Air Conditioner
- Internet
- Pet Friendly
US $385/Night
7 Nights - US $2,692
Apartment
10.0(36 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $595/Night
7 Nights - US $4,163
Apartment
10.0(33 Reviews)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $266/Night
7 Nights - US $1,860
Condo
10.0(31 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $333/Night
7 Nights - US $2,333
Apartment
10.0(29 Reviews)
3 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $547/Night
7 Nights - US $3,831
Chicago Private Villas and Holiday Homes Under $200
Over 3137+ Chicago Private Villas and Holiday Homes Under $200
Apartment
10.0(130 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $148/Night
7 Nights - US $1,036
House
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $82/Night
7 Nights - US $574
Bed & Breakfast
10.0(566 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,364
Apartment
10.0(98 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,017
Apartment
10.0(2 Reviews)
1 Bedroom
3 Guests
- Balcony/Terrace
- Air Conditioner
- Pet Friendly
- Child Friendly
US $163/Night
7 Nights - US $1,139
Apartment
10.0(64 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,118
Apartment
10.0(63 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $173/Night
7 Nights - US $1,214
Apartment
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,307
New
Apartment
10.0(58 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $152/Night
7 Nights - US $1,066
Instantly Bookable Holiday Homes in Chicago
Over 4902+ Instantly Bookable Holiday Homes in or Near Chicago
Apartment
10.0(209 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- View
- Kitchen
US $266/Night
7 Nights - US $1,861
Apartment
10.0(6 Reviews)
1 Bedroom
5 Guests
Oceanfront- Parking
- Ocean View
- View
US $190/Night
7 Nights - US $1,330
Apartment
10.0(161 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $260/Night
7 Nights - US $1,822
House
10.0(124 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,459
Apartment
10.0(123 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $520/Night
7 Nights - US $3,641
Apartment
10.0(90 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $251/Night
7 Nights - US $1,760
Apartment
10.0(89 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,164
Apartment
10.0(87 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $292/Night
7 Nights - US $2,043
Apartment
10.0(87 Reviews)
2 Bedrooms
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $255/Night
7 Nights - US $1,784
Book a Last Minute Place to Stay in Chicago
About Casai's Private Villas and Holiday Rentals in Chicago
Discover more than 8202 vacation rentals available in Chicago. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chicago.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chicago, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chicago. On average, places to stay near Chicago offer 763.36 ft², with nightly prices averaging US $377.
With Casai, finding and comparing holiday rentals in Chicago is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Chicago, IL
There are 8202 Chicago, IL Holiday Rentals
- Prices for a holiday home in Chicago start at US $7
- Top rated vacation home in Chicago is The Sono Chicago
- Most popular short term in Chicago is River Hotel
- Cheapest place to stay in Chicago is Homan Square
- Most expensive holiday rental in Chicago is Hyde Park Duplex
Recently Booked Holiday Rentals in Chicago
Frequently Asked Questions About Chicago?
What are the top holiday rentals in Chicago?
With numerous options available in Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 55th-Floor 3BR Duplex Penthouse Lake & City Views
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
How many holiday rentals have private pools in Chicago?
Discover a selection of holiday rentals with private pools near Chicago with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Chicago are best for families?
If you're searching for a family-friendly holiday home in Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chicago:
How many Casai.com holiday rentals are available in Chicago?
As of 2026, Casai boasts over 8202 properties listed in the Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1429 |
| The Loop Vacation Rentals in Chicago, Illinois | 646 |
| Near North Side Vacation Rentals in Chicago, Illinois | 592 |
| River North Vacation Rentals in Chicago, Illinois | 356 |
| South Loop Vacation Rentals in Chicago, Illinois | 297 |
| Near South Side Vacation Rentals in Chicago, Illinois | 278 |
| Lakeview Vacation Rentals in Chicago, Illinois | 255 |
| West Loop Vacation Rentals in Chicago, Illinois | 191 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 137 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 82 |
| Edgewater Vacation Rentals in Chicago, Illinois | 63 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 60 |
| Logan Square Vacation Rentals in Chicago, Illinois | 58 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 55 |
| O'Hare Vacation Rentals in Chicago, Illinois | 47 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 37 |
