Apartment
10.0(419 Reviews)
1 Bedroom
4 Guests
Parking
Pool
Ocean View
View
CA $308/Night
7 Nights - CA $2,158
Chicago Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
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Compare Holiday Rentals, Villas & Resorts in Chicago
10.0
Apartment
10.0(14 Reviews)
1 Bedroom
2 Guests
Internet
Child Friendly
CA $361/Night
7 Nights - CA $2,525
Bed & Breakfast
10.0(566 Reviews)
1 Bedroom
- Parking
Balcony/Terrace
Air Conditioner- Internet
CA $275/Night
7 Nights - CA $1,922
Apartment
10.0(252 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
CA $346/Night
7 Nights - CA $2,421
CA $293/Night
7 Nights - CA $2,051
Apartment
10.0(234 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $341/Night
7 Nights - CA $2,388
Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
CA $646/Night
7 Nights - CA $4,521
Apartment
10.0(219 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $641/Night
7 Nights - CA $4,490
Condo
10.0(219 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $415/Night
7 Nights - CA $2,902
Luxury Holiday Rentals in Chicago
Over 8097+ Luxury Holiday Rentals in or Near Chicago
Unlock the Best Price
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $7,011/Night
7 Nights - CA $49,074
New
Apartment
5 Bedrooms
12 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
CA $6,403/Night
7 Nights - CA $44,824
Bed & Breakfast
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $5,913/Night
7 Nights - CA $41,389
House
6 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $5,521/Night
7 Nights - CA $38,646
House
10.0(41 Reviews)
5 Bedrooms
14 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $5,299/Night
7 Nights - CA $37,096
CA $5,150/Night
7 Nights - CA $36,050
Apartment
8 Bedrooms
16 Guests
- Parking
- View
- Air Conditioner
- Internet
CA $5,043/Night
7 Nights - CA $35,298
House
12 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $5,034/Night
7 Nights - CA $35,235
Top-Rated Holiday Rentals with a Pool in Chicago
Over 1303+ The Best Private Villas and Holiday Rentals in Chicago with a Pool
Apartment
10.0(316 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $1,215/Night
7 Nights - CA $8,506
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $304/Night
7 Nights - CA $2,129
House
10.0(48 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $944/Night
7 Nights - CA $6,611
Apartment
10.0(46 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $259/Night
7 Nights - CA $1,812
Condo
10.0(25 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $373/Night
7 Nights - CA $2,612
Apartment
10.0(15 Reviews)
2 Bedrooms
8 Guests
Oceanfront- Parking
- Pool
- Ocean View
CA $729/Night
7 Nights - CA $5,103
Condo
10.0(14 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $428/Night
7 Nights - CA $2,997
Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $714/Night
7 Nights - CA $4,999
Apartment
10.0(9 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $674/Night
7 Nights - CA $4,716
Pet-Friendly Holiday Rentals in Chicago
Over 3241+ Pet-Friendly Holiday Rentals in or Near Chicago
Apartment
10.0(176 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $551/Night
7 Nights - CA $3,856
Apartment
10.0(5 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
CA $651/Night
7 Nights - CA $4,558
Bed & Breakfast
8.0(682 Reviews)
1 Bedroom
- Parking
- Internet
- Pet Friendly
Security/Safety
CA $224/Night
7 Nights - CA $1,567
Apartment
10.0(104 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $277/Night
7 Nights - CA $1,940
Apartment
10.0(5 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $448/Night
7 Nights - CA $3,139
Apartment
10.0(103 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $495/Night
7 Nights - CA $3,465
Apartment
10.0(96 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $214/Night
7 Nights - CA $1,502
Apartment
10.0(74 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $307/Night
7 Nights - CA $2,149
Apartment
10.0(69 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $547/Night
7 Nights - CA $3,827
Large Holiday Rentals and Private Villas in Chicago
Over 1056+ Large Holiday Rentals and Private Villas in or Near Chicago
Apartment
9.8(14 Reviews)
2 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
CA $814/Night
7 Nights - CA $5,695
Apartment
10.0(4 Reviews)
6 Bedrooms
20 Guests
Private Beach- EV Charge Station
- Parking
- Ocean View
CA $679/Night
7 Nights - CA $4,750
CA $1,208/Night
7 Nights - CA $8,455
Apartment
9.6(35 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $497/Night
7 Nights - CA $3,481
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $486/Night
7 Nights - CA $3,405
Apartment
9.6(18 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $290/Night
7 Nights - CA $2,032
Villa
9.6(13 Reviews)
1 Bedroom
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $872/Night
7 Nights - CA $6,106
Apartment
9.6(11 Reviews)
2 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $888/Night
7 Nights - CA $6,218
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $1,167/Night
7 Nights - CA $8,168
Wheelchair Accessible Holiday Homes in Chicago
Over 3068+ Wheelchair Accessible Holiday Homes in or Near Chicago
Apartment
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $406/Night
7 Nights - CA $2,842
Apartment
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
CA $989/Night
7 Nights - CA $6,921
Bed & Breakfast
9.8(219 Reviews)
1 Bedroom
Breakfast- Kitchen
- Air Conditioner
- Internet
CA $404/Night
7 Nights - CA $2,826
Apartment
10.0(59 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $377/Night
7 Nights - CA $2,636
House
10.0(2 Reviews)
1 Bedroom
8 Guests
- View
- Air Conditioner
- Internet
- Pet Friendly
CA $542/Night
7 Nights - CA $3,793
Condo
10.0(31 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $475/Night
7 Nights - CA $3,324
Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $473/Night
7 Nights - CA $3,310
Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $584/Night
7 Nights - CA $4,090
Apartment
10.0(11 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $925/Night
7 Nights - CA $6,474
Chicago Private Villas and Holiday Homes Under $200
Over 3039+ Chicago Private Villas and Holiday Homes Under $200
Apartment
10.0(64 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $225/Night
7 Nights - CA $1,575
House
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $116/Night
7 Nights - CA $809
Apartment
10.0(61 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $216/Night
7 Nights - CA $1,515
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
CA $261/Night
7 Nights - CA $1,825
Apartment
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $267/Night
7 Nights - CA $1,865
Apartment
10.0(18 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $243/Night
7 Nights - CA $1,698
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $228/Night
7 Nights - CA $1,596
Apartment
10.0(16 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $201/Night
7 Nights - CA $1,406
Instantly Bookable Holiday Homes in Chicago
Over 4792+ Instantly Bookable Holiday Homes in or Near Chicago
Apartment
10.0(158 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $387/Night
7 Nights - CA $2,708
Apartment
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $1,155/Night
7 Nights - CA $8,089
Apartment
10.0(123 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $651/Night
7 Nights - CA $4,559
Apartment
10.0(89 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $436/Night
7 Nights - CA $3,049
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
CA $351/Night
7 Nights - CA $2,456
Apartment
10.0(87 Reviews)
2 Bedrooms
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $359/Night
7 Nights - CA $2,514
House
10.0(76 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $695/Night
7 Nights - CA $4,862
Condo
10.0(68 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $386/Night
7 Nights - CA $2,700
Apartment
10.0(66 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
CA $326/Night
7 Nights - CA $2,278
Book a Last Minute Place to Stay in Chicago
About Casai's Private Villas and Holiday Rentals in Chicago
Discover more than 8106 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 763.52 ft², with nightly prices averaging CA $539.
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 in Chicago, IL
There are 8106 Chicago, IL Holiday Rentals
- Prices for a holiday home in Chicago start at CA $10
- 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
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
- 2-Story Penthouse Views, Fireplace, Pool, Gym
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.ca holiday rentals are available in Chicago?
As of 2026, Casai boasts over 8106 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 | 1403 |
| The Loop Vacation Rentals in Chicago, Illinois | 632 |
| Near North Side Vacation Rentals in Chicago, Illinois | 585 |
| River North Vacation Rentals in Chicago, Illinois | 351 |
| South Loop Vacation Rentals in Chicago, Illinois | 295 |
| Near South Side Vacation Rentals in Chicago, Illinois | 276 |
| Lakeview Vacation Rentals in Chicago, Illinois | 225 |
| West Loop Vacation Rentals in Chicago, Illinois | 186 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 129 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 72 |
| Edgewater Vacation Rentals in Chicago, Illinois | 60 |
| Logan Square Vacation Rentals in Chicago, Illinois | 55 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 54 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 53 |
| O'Hare Vacation Rentals in Chicago, Illinois | 47 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 38 |
