Resorts Space Chicago
Chicago
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Chicago

Apr 22 - Apr 23 ·
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Vacation homes in Chicago

Chicago
2 guests

Adults:

2

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Over 1,050 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
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

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

76 East 37Th Street
5.6 km (3.5 mi) from city center
1200
  • Picnic area/ Tables
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area
8.3
6 reviews
~ US$336 / night

Hamaline Luxury Guest House

5.6 km (3.5 mi) from city center
1200
  • Picnic area/ Tables
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Garden area

Hamaline Luxury Guest House

8.3
6 reviews
Average price US$ 336 / night
Popular Vacation homes destinations
Miami Beach
Orlando
Myrtle Beach
Cape Coral
St. Augustine
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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
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

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
5.5
2 reviews

Emmanuel Haven

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

Emmanuel Haven

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

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

Heavenly Abode

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
9.8
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

9.8
4 reviews
Average price US$ 361 / night
  • Guest favorite
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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
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

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
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

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
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

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!

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

Elegant Executive Residence Hot Tub Pool Parties!

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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

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

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

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

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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

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

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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

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

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

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

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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

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

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

8.3 / 10

(6 Reviews)

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

9.8 / 10

(4 Reviews)

 From 361$

Chicago Accommodation lists:

Location