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Chicago

Apr 25 - Apr 26 ·
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Vacation homes in Chicago

Chicago
2 guests

Adults:

2

Children:

0

Child’s age:

Over 1,060 stays assessed to highlight the standout picks
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Navigation

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!

Vacation Homes in Chicago

5. Emmanuel Haven

6. Heavenly Abode

7. Modern 4Br Near Six Flags & Naval Base

Vacation Homes in Chicago,Illinois with Private Pool

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

  • Popular choice
  • Beach access
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Lakefront Rooftop Parking

7346 South South Shore Drive
14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Luggage storage
  • Terrace
  • Garden area

Staying at the beachfront Lakefront Rooftop Parking Chicago villa, 6 minutes' walk from Saint Luke's Missionary Baptist Church, guests can enjoy Wi-Fi and free private parking.

7.6
10 reviews
~ US$301 / night

Lakefront Rooftop Parking

14.2 km (8.8 mi) from city center
204
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Luggage storage
  • Terrace
  • Garden area

Lakefront Rooftop Parking

Staying at the beachfront Lakefront Rooftop Parking Chicago villa, 6 minutes' walk from Saint Luke's Missionary Baptist Church, guests can enjoy Wi-Fi and free private parking.

7.6
10 reviews
Average price US$ 301 / night
  • Guest favorite
  • Beach access
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Hamaline Luxury Guest House

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

The 1-bedroom Hamaline Luxury Guest House Chicago villa boasts a location around 300 metres from Indiana Avenue Pentecostal Church of God and offers guests to enjoy temporary art galleries. Offering Wi-Fi, the property is located within a 6-km distance of the Art Institute of Chicago.

8.5
7 reviews
~ US$336 / night

Hamaline Luxury Guest House

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

Hamaline Luxury Guest House

The 1-bedroom Hamaline Luxury Guest House Chicago villa boasts a location around 300 metres from Indiana Avenue Pentecostal Church of God and offers guests to enjoy temporary art galleries. Offering Wi-Fi, the property is located within a 6-km distance of the Art Institute of Chicago.

8.5
7 reviews
Average price US$ 336 / night
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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
  • Heating

Situated merely 6 minutes' walk from Roman Susan, Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers easy access to numerous tourist spots in the area.

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
  • Heating

Luxury 9 Bedroom Villa Mins From Downtown And The Lake

Situated merely 6 minutes' walk from Roman Susan, Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago offers easy access to numerous tourist spots in the area.

9
1 reviews

Vacation Homes in Chicago

  • Great deal
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A Home Away From Home!

8858 South Constance Avenue
16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area
7.4
7 reviews

A Home Away From Home!

16.6 km (10.3 mi) from city center
161
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

A Home Away From Home!

7.4
7 reviews
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Emmanuel Haven

8139 South Blackstone Avenue
15.0 km (9.3 mi) from city center
279
  • Free parking
  • Security
  • Air conditioning

Situated about a 5-minute walk from Messiah and Saint Bartholomew Episcopal Church, the 3-bedroom Emmanuel Haven Villa Chicago offers quick access to numerous city landmarks nearby.

5.5
2 reviews

Emmanuel Haven

15.0 km (9.3 mi) from city center
279
  • Free parking
  • Security
  • Air conditioning

Emmanuel Haven

Situated about a 5-minute walk from Messiah and Saint Bartholomew Episcopal Church, the 3-bedroom Emmanuel Haven Villa Chicago offers quick access to numerous city landmarks nearby.

5.5
2 reviews
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Heavenly Abode

8157 South Dorchester Avenue
15.0 km (9.3 mi) from city center
279
  • Free parking
  • Security
  • Air conditioning
  • Heating
  • Jacuzzi

Heavenly Abode Villa Chicago is located within a 6-km distance of the Sprawling hands-on Museum of Science and Industry and provides guests with a hot tub for a more relaxing stay.

Heavenly Abode

15.0 km (9.3 mi) from city center
279
  • Free parking
  • Security
  • Air conditioning
  • Heating
  • Jacuzzi

Heavenly Abode

Heavenly Abode Villa Chicago is located within a 6-km distance of the Sprawling hands-on Museum of Science and Industry and provides guests with a hot tub for a more relaxing stay.

Vacation homes near Chicago

These options match your search but are within a one-hour drive of the city (up to 80 km / 50 mi).

Vacation Homes in Chicago,Illinois with Private Pool

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Modern 4Br Near Six Flags & Naval Base

4226 Bennett Avenue
58.2 km (36.2 mi) from Chicago
2400
  • Free parking
  • Air conditioning

Situated about 5 minutes by car from Lakehurst Shopping Center, the 2-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee entices guests to explore various tourist attractions in the area.

9.7
4 reviews
~ US$361 / night

Modern 4Br Near Six Flags & Naval Base

58.2 km (36.2 mi) from Chicago
2400
  • Free parking
  • Air conditioning

Modern 4Br Near Six Flags & Naval Base

Situated about 5 minutes by car from Lakehurst Shopping Center, the 2-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee entices guests to explore various tourist attractions in the area.

9.7
4 reviews
Average price US$ 361 / night
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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

Featuring street views, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa invites guests to visit the Sky Zone Trampoline Park, located 3.4 km away.

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

Featuring street views, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa invites guests to visit the Sky Zone Trampoline Park, located 3.4 km away.

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

320 Bellaire Avenue
26.8 km (16.7 mi) from Chicago
186
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Heating
  • Garden area

Featuring garden views, 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 10 minutes' drive from Lake Park Golf Course.

10
1 reviews

5 Star Luxury Stay Near Chicago O'Hare

26.8 km (16.7 mi) from Chicago
186
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Heating
  • Garden area

5 Star Luxury Stay Near Chicago O'Hare

Featuring garden views, 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 10 minutes' drive from Lake Park Golf Course.

10
1 reviews

Luxury Vacation Homes in Chicago

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Luxury 4Br Near Six Flags & Naval Base

1417 North Mcaree Road
59.0 km (36.7 mi) from Chicago
162
  • Free parking
  • Security
  • Air conditioning
  • Terrace

Luxury 4Br Near Six Flags & Naval Base Villa Waukegan offers quick access to such tourist spots as Clearview Park, situated merely a 5-minute walk away.

10
1 reviews

Luxury 4Br Near Six Flags & Naval Base

59.0 km (36.7 mi) from Chicago
162
  • Free parking
  • Security
  • Air conditioning
  • Terrace

Luxury 4Br Near Six Flags & Naval Base

Luxury 4Br Near Six Flags & Naval Base Villa Waukegan offers quick access to such tourist spots as Clearview Park, situated merely a 5-minute walk away.

10
1 reviews
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Elegant Executive Residence Hot Tub Pool Parties!

230 Gingerbrook Lane
45.8 km (28.5 mi) from Chicago
  • Free parking
  • Air conditioning

Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa offers proximity to nearby tourist spots, such as the BAPS Shri Swaminarayan Mandir, situated 4.5 km away.

Elegant Executive Residence Hot Tub Pool Parties!

45.8 km (28.5 mi) from Chicago
  • Free parking
  • Air conditioning

Elegant Executive Residence Hot Tub Pool Parties!

Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa offers proximity to nearby tourist spots, such as the BAPS Shri Swaminarayan Mandir, situated 4.5 km away.

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Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is 25 minutes' walk from entertainment sites such as the full - service Oselka's Snug Harbor Marina.

Sport activities include cycling and fishing.

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres

Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is 25 minutes' walk from entertainment sites such as the full - service Oselka's Snug Harbor Marina.

Sport activities include cycling and fishing.

Cheap Vacation Homes in Chicago,Illinois

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Dogwood - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 16 minutes' walk from Third Coast Surf Shop and welcomes its guests to enjoy cycling and fishing.

Relaxation options offer a sauna.

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Dogwood - Upscale 2 Bedroom Villa At Petite Acres

Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located 16 minutes' walk from Third Coast Surf Shop and welcomes its guests to enjoy cycling and fishing.

Relaxation options offer a sauna.

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Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Offering a location about a 25-minute walk from the New Buffalo Railroad Museum, Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo gives access to various tourist spots in the area.

Relaxation options offer a sauna.

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Goldenrod - Upscale 2-Bedroom Villa At Petite Acres

Offering a location about a 25-minute walk from the New Buffalo Railroad Museum, Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo gives access to various tourist spots in the area.

Relaxation options offer a sauna.

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Larkspur - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers proximity to nearby tourist spots, such as Third Coast Surf Shop, situated 16 minutes' walk away.

There is a sauna to enhance your stay. Activities in the area include cycling and fishing.

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Larkspur - Upscale 2 Bedroom Villa At Petite Acres

Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers proximity to nearby tourist spots, such as Third Coast Surf Shop, situated 16 minutes' walk away.

There is a sauna to enhance your stay. Activities in the area include cycling and fishing.

Pet Friendly Vacation Homes in Chicago

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Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located approximately a 20-minute walk from Saint Paraskevi Greek Orthodox Church and welcomes its guests to enjoy cycling and fishing. This accommodation offers guests a relaxing experience with a sauna.

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres

Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located approximately a 20-minute walk from Saint Paraskevi Greek Orthodox Church and welcomes its guests to enjoy cycling and fishing. This accommodation offers guests a relaxing experience with a sauna.

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Windflower - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers proximity to nearby tourist spots, such as the outdoor Hesston Steam Museum, situated about 7 km away.

There is a sauna to enhance your stay.

Windflower - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Windflower - Upscale 2 Bedroom Villa At Petite Acres

Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo offers proximity to nearby tourist spots, such as the outdoor Hesston Steam Museum, situated about 7 km away.

There is a sauna to enhance your stay.

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Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

1109 East Buffalo Street
75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Located approximately 20 minutes' walk from Saint Paraskevi Greek Orthodox Church, Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.

There is a sauna to enhance your stay.

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

75.7 km (47.0 mi) from Chicago
49
  • Free parking
  • Air conditioning
  • Heating
  • Sauna
  • Fitness centre
  • Garden area

Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres

Located approximately 20 minutes' walk from Saint Paraskevi Greek Orthodox Church, Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo provides access to various tourist attractions in the vicinity.

There is a sauna to enhance your stay.

Are you in a hurry?

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

Name of hotel Accommodation Rating Price, $
Lakefront Rooftop Parking

7.6 / 10

(10 Reviews)

From 301$
Hamaline Luxury Guest House

8.5 / 10

(7 Reviews)

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

9.7 / 10

(4 Reviews)

From 361$

Location