Vacation rentals in Chicago

with the largest selection, best availability, and unbeatable prices

United States

Illinois

Chicago

1-20 of 184 places to stay

Cozy Casa By Ohare Airport
Cozy Casa By Ohare Airport

Apartment

9.4 mi to the city center
5843 W Gunnison Street, Chicago, United States

Excellent

(40 reviews)

8.4

Cozy Casa By Ohare Airport Apartment Chicago lies 3.1 km from the West Belmont Avenue and approximately a 10-minute walk from Jefferson Park tube station. This apartment is situated 17 km from…

starts from

US$ 77 per one night

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Entire Apt In Heart Of Chicago
Entire Apt In Heart Of Chicago

Apartment

4.8 mi to the city center
847 West Cornelia Avenue 1N, Chicago, United States

Excellent

(10 reviews)

9.8

The spacious 1-bedroom Entire Apt In Heart Of Chicago is located approximately 9 km from Chicago Union train station and nearly a 5-minute walk from the HBTV Hearty Boys. To keep up with sports…

starts from

US$ 435 per one night

View hotel
Edgewater Andersonville-Area Apt Close To Loyola Lake Ez Parking
Edgewater Andersonville-Area Apt Close To Loyola Lake Ez Parking

Apartment

8.4 mi to the city center
1506 West Thome Avenue #2, Chicago, United States

Excellent

(6 reviews)

9.2

View hotel
New Adorable Unit Located In Historic Greystone
New Adorable Unit Located In Historic Greystone

Apartment

3 mi to the city center
3350 South Prairie Avenue, Chicago, United States

Excellent

(16 reviews)

9.6

Situated only 600 metres from Ida B Wells House, the spacious 139 m² New Adorable Unit Located In Historic Greystone Apartment Chicago also boasts easy access to Chicago Union train station which is…

View hotel
Uptown Gem
Uptown Gem

Apartment

6.5 mi to the city center
1020 West Lawrence Avenue #522, Chicago, United States

Excellent

(14 reviews)

9.4

The 42 m² Uptown Gem Apartment Chicago is located just 450 m from Paper Machete and 2.7 km from the Sheil Park Playground. Providing an indoor pool, this 1-bedroom apartment is situated a stone's…

starts from

US$ 388 per one night

View hotel
Gilean Urban Retreat
Gilean Urban Retreat

Apartment

3.3 mi to the city center
3725 South Giles Avenue, Chicago, United States

Excellent

(7 reviews)

9.6

starts from

US$ 525 per one night

View hotel
New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking
New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking

Apartment

8.5 mi to the city center
8559 South Dante Avenue, Chicago, United States

Excellent

(27 reviews)

9.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking Apartment Chicago, which is just 0.6 km from Messiah and Saint Bartholomew…

starts from

US$ 461 per one night

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Chicago - Pilsen Studio Apartment - Unit B
Chicago - Pilsen Studio Apartment - Unit B

Apartment

3281 ft to the city center
2325 South Hoyne Avenue, Chicago, United States

Excellent

(9 reviews)

9

starts from

US$ 154 per one night

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Comfortable & Relaxing Charming 3Br Unit
Comfortable & Relaxing Charming 3Br Unit

Apartment

11.9 mi to the city center
1133 West 123Rd Street 2, Chicago, United States

Excellent

(8 reviews)

9

Located within 25 minutes' walk of Whistler Woods Forest Preserve Riverside Park, the spacious 88 m² Comfortable & Relaxing Charming 3Br Unit Chicago apartment provides access to a number of tourist…

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Cozy Woodlawn Retreat 2
Cozy Woodlawn Retreat 2

Apartment

5.3 mi to the city center
6115 South Rhodes Avenue, Chicago, United States

Excellent

(6 reviews)

8.6

View hotel
Beautiful Remodeled Penthouse Unit In Old Town
Beautiful Remodeled Penthouse Unit In Old Town

Holiday home

2.4 mi to the city center
1556 North La Salle Street, Chicago, United States

Excellent

(16 reviews)

9

starts from

US$ 139 per one night

View hotel
Greater Grand Crossing/Hyde Park
Greater Grand Crossing/Hyde Park

Apartment

5.5 mi to the city center
6720 South Wabash Avenue, Chicago, United States

Good

(32 reviews)

7.4

To enjoy your vacation in Chicago, stay at the 12 m² Greater Grand Crossing/Hyde Park Apartment Chicago, which is 3.6 km from the Jackson Park and about 20 minutes' walk from White City Amusement…

starts from

US$ 149 per one night

View hotel
Hamaline Luxury Guest House
Hamaline Luxury Guest House

Villa

3 mi to the city center
76 East 37Th Street, Chicago, United States

Good

(14 reviews)

7

starts from

US$ 336 per one night

View hotel
Cozy In Hyde Park Greater Grand Crossing
Cozy In Hyde Park Greater Grand Crossing

Apartment

5.5 mi to the city center
6720 South Wabash Avenue, Chicago, United States

Good

(17 reviews)

6.8

The 1-room Cozy In Hyde Park Greater Grand Crossing Apartment Chicago lies approximately 7 km from the Guaranteed Rate Field and around 10 minutes' walk from 69th Street tube station. This 12 m²…

starts from

US$ 186 per one night

View hotel
Beautiful 4 Bedroom Apartment Near Everything
Beautiful 4 Bedroom Apartment Near Everything

Apartment

8.9 mi to the city center
8927 South Blackstone Avenue, Chicago, United States

Good

(17 reviews)

6.4

Located 7 km from the Oriental Institute Museum, the 177 m² Beautiful 4 Bedroom 2 Bathroom Apartment Near Everything Chicago overlooks the garden. This 2-bedroom apartment offers modern facilities…

starts from

US$ 643 per one night

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Close To Downtown - Free Parking
Close To Downtown - Free Parking

Homestay

2.9 mi to the city center
944 West 52Nd Street, Chicago, United States

Average

(10 reviews)

5.6

starts from

US$ 34 per one night

View hotel
Comfort West Urban Chicago Loft House
Comfort West Urban Chicago Loft House

Apartment

7.6 mi to the city center
5908 West Fullerton Avenue, Chicago, United States

Good

(9 reviews)

7.4

starts from

US$ 340 per one night

View hotel
Beautiful Home Near Downtwon - Free Parking!
Beautiful Home Near Downtwon - Free Parking!

Homestay

2.9 mi to the city center
939 West 51St Place, Chicago, United States

Good

(12 reviews)

7.2

The 7-room Beautiful Home Near Downtwon - Free Parking! Chicago apartment is located within a 9-km distance of Chicago Union train station and in close proximity to House of Prayer for All People.

starts from

US$ 52 per one night

View hotel
Hyde Park Shared Apartments
Hyde Park Shared Apartments

Apartment

5 mi to the city center
Hyde Park

Good

(6 reviews)

6.2

starts from

US$ 119 per one night

View hotel
Lakefront Rooftop Parking
Lakefront Rooftop Parking

Villa

8.2 mi to the city center
7346 South South Shore Drive, Chicago, United States

Good

(11 reviews)

7.4

Situated just a 6-minute walk from Windsor Park Lutheran Church, the beachfront Lakefront Rooftop Parking Chicago villa entices guests with views of the lake. Located 3.9 km from the Sprawling hands…

starts from

US$ 301 per one night

View hotel

Cozy Casa By Ohare Airport

Apartment

9.4 mi to the city center

5843 W Gunnison Street, Chicago, United States

Excellent

(40 reviews)

8.4

Cozy Casa By Ohare Airport Apartment Chicago lies 3.1 km from the West Belmont Avenue and approximately a 10-minute walk from Jefferson Park tube station. This apartment is situated 17 km from…

starts from

US$ 77 per one night

View hotel

Entire Apt In Heart Of Chicago

Apartment

4.8 mi to the city center

847 West Cornelia Avenue 1N, Chicago, United States

Excellent

(10 reviews)

9.8

The spacious 1-bedroom Entire Apt In Heart Of Chicago is located approximately 9 km from Chicago Union train station and nearly a 5-minute walk from the HBTV Hearty Boys. To keep up with sports…

starts from

US$ 435 per one night

View hotel

Edgewater Andersonville-Area Apt Close To Loyola Lake Ez Parking

Apartment

8.4 mi to the city center

1506 West Thome Avenue #2, Chicago, United States

Excellent

(6 reviews)

9.2

View hotel

New Adorable Unit Located In Historic Greystone

Apartment

3 mi to the city center

3350 South Prairie Avenue, Chicago, United States

Excellent

(16 reviews)

9.6

Situated only 600 metres from Ida B Wells House, the spacious 139 m² New Adorable Unit Located In Historic Greystone Apartment Chicago also boasts easy access to Chicago Union train station which is…

View hotel

Uptown Gem

Apartment

6.5 mi to the city center

1020 West Lawrence Avenue #522, Chicago, United States

Excellent

(14 reviews)

9.4

The 42 m² Uptown Gem Apartment Chicago is located just 450 m from Paper Machete and 2.7 km from the Sheil Park Playground. Providing an indoor pool, this 1-bedroom apartment is situated a stone's…

starts from

US$ 388 per one night

View hotel

Gilean Urban Retreat

Apartment

3.3 mi to the city center

3725 South Giles Avenue, Chicago, United States

Excellent

(7 reviews)

9.6

starts from

US$ 525 per one night

View hotel

New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking

Apartment

8.5 mi to the city center

8559 South Dante Avenue, Chicago, United States

Excellent

(27 reviews)

9.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking Apartment Chicago, which is just 0.6 km from Messiah and Saint Bartholomew…

starts from

US$ 461 per one night

View hotel

Chicago - Pilsen Studio Apartment - Unit B

Apartment

3281 ft to the city center

2325 South Hoyne Avenue, Chicago, United States

Excellent

(9 reviews)

starts from

US$ 154 per one night

View hotel

Comfortable & Relaxing Charming 3Br Unit

Apartment

11.9 mi to the city center

1133 West 123Rd Street 2, Chicago, United States

Excellent

(8 reviews)

Located within 25 minutes' walk of Whistler Woods Forest Preserve Riverside Park, the spacious 88 m² Comfortable & Relaxing Charming 3Br Unit Chicago apartment provides access to a number of tourist…

View hotel

Cozy Woodlawn Retreat 2

Apartment

5.3 mi to the city center

6115 South Rhodes Avenue, Chicago, United States

Excellent

(6 reviews)

8.6

View hotel

Beautiful Remodeled Penthouse Unit In Old Town

Holiday home

2.4 mi to the city center

1556 North La Salle Street, Chicago, United States

Excellent

(16 reviews)

starts from

US$ 139 per one night

View hotel

Greater Grand Crossing/Hyde Park

Apartment

5.5 mi to the city center

6720 South Wabash Avenue, Chicago, United States

Good

(32 reviews)

7.4

To enjoy your vacation in Chicago, stay at the 12 m² Greater Grand Crossing/Hyde Park Apartment Chicago, which is 3.6 km from the Jackson Park and about 20 minutes' walk from White City Amusement…

starts from

US$ 149 per one night

View hotel

Hamaline Luxury Guest House

Villa

3 mi to the city center

76 East 37Th Street, Chicago, United States

Good

(14 reviews)

starts from

US$ 336 per one night

View hotel

Cozy In Hyde Park Greater Grand Crossing

Apartment

5.5 mi to the city center

6720 South Wabash Avenue, Chicago, United States

Good

(17 reviews)

6.8

The 1-room Cozy In Hyde Park Greater Grand Crossing Apartment Chicago lies approximately 7 km from the Guaranteed Rate Field and around 10 minutes' walk from 69th Street tube station. This 12 m²…

starts from

US$ 186 per one night

View hotel

Beautiful 4 Bedroom Apartment Near Everything

Apartment

8.9 mi to the city center

8927 South Blackstone Avenue, Chicago, United States

Good

(17 reviews)

6.4

Located 7 km from the Oriental Institute Museum, the 177 m² Beautiful 4 Bedroom 2 Bathroom Apartment Near Everything Chicago overlooks the garden. This 2-bedroom apartment offers modern facilities…

starts from

US$ 643 per one night

View hotel

Close To Downtown - Free Parking

Homestay

2.9 mi to the city center

944 West 52Nd Street, Chicago, United States

Average

(10 reviews)

5.6

starts from

US$ 34 per one night

View hotel

Comfort West Urban Chicago Loft House

Apartment

7.6 mi to the city center

5908 West Fullerton Avenue, Chicago, United States

Good

(9 reviews)

7.4

starts from

US$ 340 per one night

View hotel

Beautiful Home Near Downtwon - Free Parking!

Homestay

2.9 mi to the city center

939 West 51St Place, Chicago, United States

Good

(12 reviews)

7.2

The 7-room Beautiful Home Near Downtwon - Free Parking! Chicago apartment is located within a 9-km distance of Chicago Union train station and in close proximity to House of Prayer for All People.

starts from

US$ 52 per one night

View hotel

Hyde Park Shared Apartments

Apartment

5 mi to the city center

Hyde Park

Good

(6 reviews)

6.2

starts from

US$ 119 per one night

View hotel

Lakefront Rooftop Parking

Villa

8.2 mi to the city center

7346 South South Shore Drive, Chicago, United States

Good

(11 reviews)

7.4

Situated just a 6-minute walk from Windsor Park Lutheran Church, the beachfront Lakefront Rooftop Parking Chicago villa entices guests with views of the lake. Located 3.9 km from the Sprawling hands…

starts from

US$ 301 per one night

View hotel

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Hotels (124) Vacation rentals (184)

184 properties found

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Cozy Casa By Ohare Airport
Cozy Casa By Ohare Airport

Apartment

9.4 mi to the city center
5843 W Gunnison Street, Chicago, United States

Excellent

(40 reviews)

8.4

Cozy Casa By Ohare Airport Apartment Chicago lies 3.1 km from the West Belmont Avenue and approximately a 10-minute walk from Jefferson Park tube station. This apartment is situated 17 km from…

starts from

US$ 77 per one night

View hotel
Entire Apt In Heart Of Chicago
Entire Apt In Heart Of Chicago

Apartment

4.8 mi to the city center
847 West Cornelia Avenue 1N, Chicago, United States

Excellent

(10 reviews)

9.8

The spacious 1-bedroom Entire Apt In Heart Of Chicago is located approximately 9 km from Chicago Union train station and nearly a 5-minute walk from the HBTV Hearty Boys. To keep up with sports…

starts from

US$ 435 per one night

View hotel
Edgewater Andersonville-Area Apt Close To Loyola Lake Ez Parking
Edgewater Andersonville-Area Apt Close To Loyola Lake Ez Parking

Apartment

8.4 mi to the city center
1506 West Thome Avenue #2, Chicago, United States

Excellent

(6 reviews)

9.2

View hotel
New Adorable Unit Located In Historic Greystone
New Adorable Unit Located In Historic Greystone

Apartment

3 mi to the city center
3350 South Prairie Avenue, Chicago, United States

Excellent

(16 reviews)

9.6

Situated only 600 metres from Ida B Wells House, the spacious 139 m² New Adorable Unit Located In Historic Greystone Apartment Chicago also boasts easy access to Chicago Union train station which is…

View hotel
Uptown Gem
Uptown Gem

Apartment

6.5 mi to the city center
1020 West Lawrence Avenue #522, Chicago, United States

Excellent

(14 reviews)

9.4

The 42 m² Uptown Gem Apartment Chicago is located just 450 m from Paper Machete and 2.7 km from the Sheil Park Playground. Providing an indoor pool, this 1-bedroom apartment is situated a stone's…

starts from

US$ 388 per one night

View hotel
Gilean Urban Retreat
Gilean Urban Retreat

Apartment

3.3 mi to the city center
3725 South Giles Avenue, Chicago, United States

Excellent

(7 reviews)

9.6

starts from

US$ 525 per one night

View hotel
New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking
New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking

Apartment

8.5 mi to the city center
8559 South Dante Avenue, Chicago, United States

Excellent

(27 reviews)

9.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom New Luxurious 5Bd-2Ba Duplex-Free Wine-2Car Parking Apartment Chicago, which is just 0.6 km from Messiah and Saint Bartholomew…

starts from

US$ 461 per one night

View hotel
Chicago - Pilsen Studio Apartment - Unit B
Chicago - Pilsen Studio Apartment - Unit B

Apartment

3281 ft to the city center
2325 South Hoyne Avenue, Chicago, United States

Excellent

(9 reviews)

9

starts from

US$ 154 per one night

View hotel
Comfortable & Relaxing Charming 3Br Unit
Comfortable & Relaxing Charming 3Br Unit

Apartment

11.9 mi to the city center
1133 West 123Rd Street 2, Chicago, United States

Excellent

(8 reviews)

9

Located within 25 minutes' walk of Whistler Woods Forest Preserve Riverside Park, the spacious 88 m² Comfortable & Relaxing Charming 3Br Unit Chicago apartment provides access to a number of tourist…

View hotel
Cozy Woodlawn Retreat 2
Cozy Woodlawn Retreat 2

Apartment

5.3 mi to the city center
6115 South Rhodes Avenue, Chicago, United States

Excellent

(6 reviews)

8.6

View hotel
Beautiful Remodeled Penthouse Unit In Old Town
Beautiful Remodeled Penthouse Unit In Old Town

Holiday home

2.4 mi to the city center
1556 North La Salle Street, Chicago, United States

Excellent

(16 reviews)

9

starts from

US$ 139 per one night

View hotel
Greater Grand Crossing/Hyde Park
Greater Grand Crossing/Hyde Park

Apartment

5.5 mi to the city center
6720 South Wabash Avenue, Chicago, United States

Good

(32 reviews)

7.4

To enjoy your vacation in Chicago, stay at the 12 m² Greater Grand Crossing/Hyde Park Apartment Chicago, which is 3.6 km from the Jackson Park and about 20 minutes' walk from White City Amusement…

starts from

US$ 149 per one night

View hotel
Hamaline Luxury Guest House
Hamaline Luxury Guest House

Villa

3 mi to the city center
76 East 37Th Street, Chicago, United States

Good

(14 reviews)

7

starts from

US$ 336 per one night

View hotel
Cozy In Hyde Park Greater Grand Crossing
Cozy In Hyde Park Greater Grand Crossing

Apartment

5.5 mi to the city center
6720 South Wabash Avenue, Chicago, United States

Good

(17 reviews)

6.8

The 1-room Cozy In Hyde Park Greater Grand Crossing Apartment Chicago lies approximately 7 km from the Guaranteed Rate Field and around 10 minutes' walk from 69th Street tube station. This 12 m²…

starts from

US$ 186 per one night

View hotel
Beautiful 4 Bedroom Apartment Near Everything
Beautiful 4 Bedroom Apartment Near Everything

Apartment

8.9 mi to the city center
8927 South Blackstone Avenue, Chicago, United States

Good

(17 reviews)

6.4

Located 7 km from the Oriental Institute Museum, the 177 m² Beautiful 4 Bedroom 2 Bathroom Apartment Near Everything Chicago overlooks the garden. This 2-bedroom apartment offers modern facilities…

starts from

US$ 643 per one night

View hotel
Close To Downtown - Free Parking
Close To Downtown - Free Parking

Homestay

2.9 mi to the city center
944 West 52Nd Street, Chicago, United States

Average

(10 reviews)

5.6

starts from

US$ 34 per one night

View hotel
Comfort West Urban Chicago Loft House
Comfort West Urban Chicago Loft House

Apartment

7.6 mi to the city center
5908 West Fullerton Avenue, Chicago, United States

Good

(9 reviews)

7.4

starts from

US$ 340 per one night

View hotel
Beautiful Home Near Downtwon - Free Parking!
Beautiful Home Near Downtwon - Free Parking!

Homestay

2.9 mi to the city center
939 West 51St Place, Chicago, United States

Good

(12 reviews)

7.2

The 7-room Beautiful Home Near Downtwon - Free Parking! Chicago apartment is located within a 9-km distance of Chicago Union train station and in close proximity to House of Prayer for All People.

starts from

US$ 52 per one night

View hotel
Hyde Park Shared Apartments
Hyde Park Shared Apartments

Apartment

5 mi to the city center
Hyde Park

Good

(6 reviews)

6.2

starts from

US$ 119 per one night

View hotel
Lakefront Rooftop Parking
Lakefront Rooftop Parking

Villa

8.2 mi to the city center
7346 South South Shore Drive, Chicago, United States

Good

(11 reviews)

7.4

Situated just a 6-minute walk from Windsor Park Lutheran Church, the beachfront Lakefront Rooftop Parking Chicago villa entices guests with views of the lake. Located 3.9 km from the Sprawling hands…

starts from

US$ 301 per one night

View hotel

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