Chicago
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2

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0

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Chicago

Nov 03 - Nov 04 ·
2 guests

Chicago Vacation Rentals

Chicago
2 guests

Adults:

2

Children:

0

Child’s age:

Over 1,060 stays assessed to highlight the standout picks
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1. Lakefront Rooftop Parking

2. Hamaline Luxury Guest House

3. Luxury 9 Bedroom Villa Mins From Downtown And The Lake

4. A Home Away From Home!

Cheap Chicago Vacation Rentals

5. Emmanuel Haven

6. Heavenly Abode

7. Modern 4Br Near Six Flags & Naval Base

Pet Friendly Vacation Rentals Chicago

8. Urban Oasis In Chicago'S Best Suburb

9. 5 Star Luxury Stay Near Chicago O'Hare

10. Luxury 4Br Near Six Flags & Naval Base

Chicago Luxury Vacation Rentals

  • Beach access
Lakefront Rooftop Parking Lakefront Rooftop Parking

Lakefront Rooftop Parking

7346 South South Shore Drive
14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Mini-bar
  • Terrace

Featuring lake views, the 3-bedroom Lakefront Rooftop Parking Chicago villa invites guests to visit the private research University of Chicago, located around 10 minutes away by car.

7.5
11 reviews
~ US$301 / night

Lakefront Rooftop Parking

14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Mini-bar
  • Terrace

Lakefront Rooftop Parking

Featuring lake views, the 3-bedroom Lakefront Rooftop Parking Chicago villa invites guests to visit the private research University of Chicago, located around 10 minutes away by car.

7.5
11 reviews
From US$ 301 / night
  • Popular choice
  • Beach access
Hamaline Luxury Guest House Hamaline Luxury Guest House

Hamaline Luxury Guest House

76 East 37Th Street
5.6 km (3.5 mi) from city center
1400
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area

Along with Wi-Fi and a car park, Hamaline Luxury Guest House Chicago villa offers proximity to the super - tall skyscraper "Willis Tower", located 6 km away.

7.1
14 reviews
~ US$336 / night

Hamaline Luxury Guest House

5.6 km (3.5 mi) from city center
1400
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area

Hamaline Luxury Guest House

Along with Wi-Fi and a car park, Hamaline Luxury Guest House Chicago villa offers proximity to the super - tall skyscraper "Willis Tower", located 6 km away.

7.1
14 reviews
From US$ 336 / night
Luxury 9 Bedroom Villa Mins From Downtown And The Lake Luxury 9 Bedroom Villa Mins From Downtown And The Lake

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

6417 North Magnolia Avenue
13.7 km (8.5 mi) from city center
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating

Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago, located a 6-minute walk from Roman Susan, can host up to 19 guests.

9
1 reviews

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

13.7 km (8.5 mi) from city center
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Heating

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago, located a 6-minute walk from Roman Susan, can host up to 19 guests.

9
1 reviews

Cheap Chicago Vacation Rentals

  • Great deal
A Home Away From Home! A Home Away From Home!

A Home Away From Home!

8858 South Constance Avenue
16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities

Located a 16-minute walk from Bronzeville Children's Museum, A Home Away From Home! Chicago gives access to various tourist sites in the vicinity.

7.4
7 reviews

A Home Away From Home!

16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Tea and coffee facilities

A Home Away From Home!

Located a 16-minute walk from Bronzeville Children's Museum, A Home Away From Home! Chicago gives access to various tourist sites in the vicinity.

7.4
7 reviews
Emmanuel Haven Emmanuel Haven

Emmanuel Haven

8139 South Blackstone Avenue
15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio

Located just 400 metres from Faith Tabernacle M.B. Church, the 5-bedroom Emmanuel Haven Villa Chicago provides access to various tourist attractions in the vicinity.

5.5
2 reviews

Emmanuel Haven

15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio

Emmanuel Haven

Located just 400 metres from Faith Tabernacle M.B. Church, the 5-bedroom Emmanuel Haven Villa Chicago provides access to various tourist attractions in the vicinity.

5.5
2 reviews
Heavenly Abode Heavenly Abode

Heavenly Abode

8157 South Dorchester Avenue
15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities

Offering a Jacuzzi, the 1-bedroom Heavenly Abode Villa Chicago is located around a 25-minute walk from Nat King Cole Park.

Heavenly Abode

15.0 km (9.3 mi) from city center
279
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities

Heavenly Abode

Offering a Jacuzzi, the 1-bedroom Heavenly Abode Villa Chicago is located around a 25-minute walk from Nat King Cole Park.

Vacation rentals near Chicago

Pet Friendly Vacation Rentals Chicago

Modern 4Br Near Six Flags & Naval Base Modern 4Br Near Six Flags & Naval Base

Modern 4Br Near Six Flags & Naval Base

4226 Bennett Avenue
58.2 km (36.2 mi) from Chicago
2400
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Patio

Located about a 25-minute walk from the sprawling amusement park "Six Flags Great America", the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee gives access to various tourist sites in the vicinity. This 2-bathroom villa hosts up to 10 guests and provides them with private car parking.

10
6 reviews
~ US$361 / night

Modern 4Br Near Six Flags & Naval Base

58.2 km (36.2 mi) from Chicago
2400
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Patio

Modern 4Br Near Six Flags & Naval Base

Located about a 25-minute walk from the sprawling amusement park "Six Flags Great America", the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee gives access to various tourist sites in the vicinity. This 2-bathroom villa hosts up to 10 guests and provides them with private car parking.

10
6 reviews
From US$ 361 / night
  • Guest favorite
Urban Oasis In Chicago'S Best Suburb Urban Oasis In Chicago'S Best Suburb

Urban Oasis In Chicago'S Best Suburb

905 Bradford Drive
48.1 km (29.9 mi) from Chicago
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Luggage storage

Hosting up to 6 guests, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa offers a convenient location around 10 minutes' drive from the Classic Riverwalk Urban Park.

9.2
7 reviews

Urban Oasis In Chicago'S Best Suburb

48.1 km (29.9 mi) from Chicago
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Luggage storage

Urban Oasis In Chicago'S Best Suburb

Hosting up to 6 guests, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa offers a convenient location around 10 minutes' drive from the Classic Riverwalk Urban Park.

9.2
7 reviews
5 Star Luxury Stay Near Chicago O'Hare 5 Star Luxury Stay Near Chicago O'Hare

5 Star Luxury Stay Near Chicago O'Hare

320 Bellaire Avenue
26.8 km (16.7 mi) from Chicago
186
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Garden area

The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 3.9 km from Flick Park, giving access to various tourist spots nearby.

10
1 reviews

5 Star Luxury Stay Near Chicago O'Hare

26.8 km (16.7 mi) from Chicago
186
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Garden area

5 Star Luxury Stay Near Chicago O'Hare

The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 3.9 km from Flick Park, giving access to various tourist spots nearby.

10
1 reviews

Chicago Vacation Rentals Oceanfront

Luxury 4Br Near Six Flags & Naval Base Luxury 4Br Near Six Flags & Naval Base

Luxury 4Br Near Six Flags & Naval Base

1417 North Mcaree Road
59.0 km (36.7 mi) from Chicago
162
  • BBQ facilities
  • Free parking
  • Housekeeping
  • Air conditioning
  • Flat-screen TV
  • Terrace

Situated just a 5-minute walk from Clearview Park, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan entices guests with views of the garden.

10
2 reviews

Luxury 4Br Near Six Flags & Naval Base

59.0 km (36.7 mi) from Chicago
162
  • BBQ facilities
  • Free parking
  • Housekeeping
  • Air conditioning
  • Flat-screen TV
  • Terrace

Luxury 4Br Near Six Flags & Naval Base

Situated just a 5-minute walk from Clearview Park, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan entices guests with views of the garden.

10
2 reviews
Elegant Executive Residence Hot Tub Pool Parties! Elegant Executive Residence Hot Tub Pool Parties!

Elegant Executive Residence Hot Tub Pool Parties!

230 Gingerbrook Lane
45.8 km (28.5 mi) from Chicago
2388
  • Free parking
  • Air conditioning
  • Flat-screen TV

Staying at the 1-bedroom Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa, guests can visit Bartlett Park District T, which is nearly 25 minutes' walk away.

Elegant Executive Residence Hot Tub Pool Parties!

45.8 km (28.5 mi) from Chicago
2388
  • Free parking
  • Air conditioning
  • Flat-screen TV

Elegant Executive Residence Hot Tub Pool Parties!

Staying at the 1-bedroom Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa, guests can visit Bartlett Park District T, which is nearly 25 minutes' walk away.

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo, located 2.2 km from Galien River County Nature Park, invites guests to relax in a sauna.

The area is popular for those who like cycling and fisheries.

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo, located 2.2 km from Galien River County Nature Park, invites guests to relax in a sauna.

The area is popular for those who like cycling and fisheries.

Chicago Vacation Rentals with Private Pool

Dogwood - Upscale 2 Bedroom Villa At Petite Acres Dogwood - Upscale 2 Bedroom Villa At Petite Acres

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Offering access to entertainment venues such as the full - service Oselka's Snug Harbor Marina, situated around 25 minutes' walk away, the 2-bedroom Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo can host up to 4 guests. Pampering guests with a sauna, this property features views of the lake and is nestled 2.2 km from Galien River County Nature Park.

Guests can enjoy cycling and fisheries, which can be arranged onsite.

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

Offering access to entertainment venues such as the full - service Oselka's Snug Harbor Marina, situated around 25 minutes' walk away, the 2-bedroom Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo can host up to 4 guests. Pampering guests with a sauna, this property features views of the lake and is nestled 2.2 km from Galien River County Nature Park.

Guests can enjoy cycling and fisheries, which can be arranged onsite.

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

The 2-bedroom Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is nestled within 7 km of the outdoor Hesston Steam Museum and provides a sauna.

There is cycling and fisheries available on-site.

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

The 2-bedroom Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is nestled within 7 km of the outdoor Hesston Steam Museum and provides a sauna.

There is cycling and fisheries available on-site.

Larkspur - Upscale 2 Bedroom Villa At Petite Acres Larkspur - Upscale 2 Bedroom Villa At Petite Acres

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

The comfortable 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel is within 10 minutes' drive of Galien River County Nature Park and boasts a casino, a sauna, and a golf course.

Guests can access a casino to add excitement to their stay. The area is known for cycling and fisheries.

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

The comfortable 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel is within 10 minutes' drive of Galien River County Nature Park and boasts a casino, a sauna, and a golf course.

Guests can access a casino to add excitement to their stay. The area is known for cycling and fisheries.

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

The 2-bedroom Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located within a 7-km distance of the outdoor Hesston Steam Museum and provides guests with a sauna for a more relaxing stay.

Cycling and fisheries can be enjoyed nearby and a fitness room is available onsite.

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

The 2-bedroom Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located within a 7-km distance of the outdoor Hesston Steam Museum and provides guests with a sauna for a more relaxing stay.

Cycling and fisheries can be enjoyed nearby and a fitness room is available onsite.

Windflower - Upscale 2 Bedroom Villa At Petite Acres Windflower - Upscale 2 Bedroom Villa At Petite Acres

Windflower - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

The 2-bedroom Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices active guests with access to a fitness area and is located about 25 minutes on foot from New Buffalo Railroad Museum.

Relax at a sauna, where you can enjoy the rest in full. There is a casino, along with cycling and fisheries to diversify guests' leisure.

Windflower - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Windflower - Upscale 2 Bedroom Villa At Petite Acres

The 2-bedroom Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices active guests with access to a fitness area and is located about 25 minutes on foot from New Buffalo Railroad Museum.

Relax at a sauna, where you can enjoy the rest in full. There is a casino, along with cycling and fisheries to diversify guests' leisure.

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is nearly a 25-minute stroll from entertainment sites such as the full - service Oselka's Snug Harbor Marina. The New Buffalo villa hosts up to 4 guests and provides a casino for their enjoyment.

If you would like stay in shape, try cycling and fisheries at the New Buffalo accommodation.

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is nearly a 25-minute stroll from entertainment sites such as the full - service Oselka's Snug Harbor Marina. The New Buffalo villa hosts up to 4 guests and provides a casino for their enjoyment.

If you would like stay in shape, try cycling and fisheries at the New Buffalo accommodation.

Woodsage - Upscale 2 Bedroom Villa At Petite Acres Woodsage - Upscale 2 Bedroom Villa At Petite Acres

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Offering a sauna for a relaxing experience, the luxurious Woodsage - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located a 25-minute walk from the full-service Oselka's Snug Harbor Marina. Providing guests with Wi-Fi and a private parking lot, the 2-bedroom villa is 3.9 km from Whittaker Woods Golf Course.

There are a casino provided for guests' enjoyment, along with a fitness room for guests to stay fit. Onsite sport activities include cycling and fisheries.

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Sauna
  • Garden area

Woodsage - Upscale 2 Bedroom Villa At Petite Acres

Offering a sauna for a relaxing experience, the luxurious Woodsage - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located a 25-minute walk from the full-service Oselka's Snug Harbor Marina. Providing guests with Wi-Fi and a private parking lot, the 2-bedroom villa is 3.9 km from Whittaker Woods Golf Course.

There are a casino provided for guests' enjoyment, along with a fitness room for guests to stay fit. Onsite sport activities include cycling and fisheries.

Are you in a hurry?

Here is a quick list of Vacation Rentals in Chicago, selected based on their rating

Name of hotel Accommodation Rating Price, $
Lakefront Rooftop Parking

7.5 / 10

(11 Reviews)

From 301$
Hamaline Luxury Guest House

7.1 / 10

(14 Reviews)

From 336$
Modern 4Br Near Six Flags & Naval Base

10.0 / 10

(6 Reviews)

From 361$

Chicago and related destinations

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