Vacation rentals in Chicago

with the largest selection, best availability, and unbeatable prices

United States

Illinois

Chicago

1-20 of 184 places to stay

Flexhome Wicker Park - Stylish 2Br - Sleeps 6
Flexhome Wicker Park - Stylish 2Br - Sleeps 6

Apartment

2.9 mi to the city center
2149 W Division St, Chicago, Il 60622, Usa, Chicago, United States

Excellent

(8 reviews)

8.4

starts from

US$ 629 per one night

View hotel
Little India Gem - Bollywood Retreat Near Markets
Little India Gem - Bollywood Retreat Near Markets

Apartment

8.9 mi to the city center
#2, 2508 West Devon Avenue, Chicago, United States

Excellent

(6 reviews)

9

View hotel
Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field
Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center
2036 South Michigan Avenue 605, Chicago, United States

Excellent

(10 reviews)

8.6

starts from

US$ 414 per one night

View hotel
Chic 2 Bedroom 1 Parking Sleeps 6
Chic 2 Bedroom 1 Parking Sleeps 6

Apartment

1.5 mi to the city center
33 South Ashland Avenue, Chicago, United States

Excellent

(9 reviews)

9.4

starts from

US$ 510 per one night

View hotel
Woodlawn Oasis
Woodlawn Oasis

Holiday home

6.1 mi to the city center
6433 South Minerva Avenue, Chicago, United States

Excellent

(13 reviews)

9

The 3-bedroom Woodlawn Oasis Villa Chicago offers swift access to various city sites, such as Woodlawn Baptist Church, situated about a 5-minute walk away. Located a mere 1.4 km from the leading…

starts from

US$ 526 per one night

View hotel
Ace Properties
Ace Properties

Apartment

6.3 mi to the city center
3317 North Avers Avenue, Chicago, United States

Excellent

(10 reviews)

9.8

starts from

US$ 642 per one night

View hotel
West Loop - City Views With In & Out Parking 5
West Loop - City Views With In & Out Parking 5

Apartment

2953 ft to the city center
315 South Peoria Street, Chicago, United States

Excellent

(5 reviews)

9.4

starts from

US$ 912 per one night

View hotel
Livn West Loop Chicago Classic Queen Studio
Livn West Loop Chicago Classic Queen Studio

Apartment

984 ft to the city center
555 West Jackson Boulevard, Chicago, United States

Excellent

(62 reviews)

9

starts from

US$ 242 per one night

View hotel
Boho Bliss - 1Br, 1Bath W/Patio!
Boho Bliss - 1Br, 1Bath W/Patio!

Apartment

4.3 mi to the city center
1813 North Kedzie Avenue 3, Chicago, United States

Excellent

(36 reviews)

9

Boho Bliss - 1Br, 1Bath W/Patio! Apartment Chicago is situated a 5-minute walk from Chua Lien Hoa Buddhist Temple and 20 km from Chicago Midway International airport. This apartment is situated 10 km…

starts from

US$ 197 per one night

View hotel
Modern Apt W Private Entrance Washer Dryer Free Parking
Modern Apt W Private Entrance Washer Dryer Free Parking

Apartment

10.3 mi to the city center
2947 West Fargo Avenue, Chicago, United States

Excellent

(6 reviews)

9.2

To enjoy your vacation in Chicago, stay at the 1-room A Charming Modern Chic Basement Apartment Chicago, which is 2.6 km from the Devon Avenue and within 15 minutes' walk of the James Park. The 46 m²…

starts from

US$ 265 per one night

View hotel
Livn Millennium Park Downtown Chicago Superior 2 Br
Livn Millennium Park Downtown Chicago Superior 2 Br

Apartment

4265 ft to the city center
19 South Wabash Avenue, Chicago, United States

Excellent

(9 reviews)

9.2

starts from

US$ 555 per one night

View hotel
Comfy Garden Suite In Andersonville
Comfy Garden Suite In Andersonville

Apartment

7.2 mi to the city center
5315 North Glenwood Avenue, Chicago, United States

Excellent

(5 reviews)

9

starts from

US$ 191 per one night

View hotel
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center
2036 South Michigan Avenue Unit 306, Chicago, United States

Excellent

(10 reviews)

8.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field Chicago apartment, which is 350 metres…

starts from

US$ 442 per one night

View hotel
Lower Level Luxury
Lower Level Luxury

Apartment

9.2 mi to the city center
6254 W Cuyler Ave, Chicago, United States

Excellent

(10 reviews)

9.6

starts from

US$ 85 per one night

View hotel
Livn West Loop Chicago Queen Superior Studio
Livn West Loop Chicago Queen Superior Studio

Apartment

Map
555 West Jackson Boulevard, Chicago, United States

Excellent

(93 reviews)

9.2

View hotel
Cozy 1Br Retreat Near Transit, Dining And Parking
Cozy 1Br Retreat Near Transit, Dining And Parking

Apartment

9 mi to the city center
1727 West North Shore Avenue, Chicago, United States

Excellent

(11 reviews)

9.4

starts from

US$ 144 per one night

View hotel
Charming Chicago Apt
Charming Chicago Apt

Apartment

1.2 mi to the city center
2207 West 18Th Street, Chicago, United States

Excellent

(22 reviews)

8.4

To enjoy your vacation in Chicago, stay at Charming Chicago Apt, which is approximately 7 km from the Magnificent Mile and approximately 25 minutes' walk from the Douglas Park. The apartment is…

starts from

US$ 342 per one night

View hotel
Livn Millennium Park Downtown Chicago Superior 1Br
Livn Millennium Park Downtown Chicago Superior 1Br

Apartment

4265 ft to the city center
19 South Wabash Avenue, Chicago, United States

Excellent

(15 reviews)

9.4

View hotel
Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access
Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access

Apartment

2.5 mi to the city center
1335 North Greenview Avenue 1F, Chicago, United States

Excellent

(24 reviews)

9.6

The 46 m² Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access Apartment Chicago offers easy entry to such city sights as the St. Stanislaus Kostka Church, situated nearly a 5-minute walk…

starts from

US$ 243 per one night

View hotel
Wrigley 2Br, 1Ba With Free Parking
Wrigley 2Br, 1Ba With Free Parking

Apartment

5.2 mi to the city center
Lakeview

Excellent

(10 reviews)

8.6

The spacious Wrigley 2Br, 1Ba With Free Parking Apartment Chicago is located 1.4 km from the Wrigley Field and a 5-minute walk from Juniper Park. This apartment is situated within 10 km of Chicago…

starts from

US$ 530 per one night

View hotel

Flexhome Wicker Park - Stylish 2Br - Sleeps 6

Apartment

2.9 mi to the city center

2149 W Division St, Chicago, Il 60622, Usa, Chicago, United States

Excellent

(8 reviews)

8.4

starts from

US$ 629 per one night

View hotel

Little India Gem - Bollywood Retreat Near Markets

Apartment

8.9 mi to the city center

#2, 2508 West Devon Avenue, Chicago, United States

Excellent

(6 reviews)

View hotel

Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center

2036 South Michigan Avenue 605, Chicago, United States

Excellent

(10 reviews)

8.6

starts from

US$ 414 per one night

View hotel

Chic 2 Bedroom 1 Parking Sleeps 6

Apartment

1.5 mi to the city center

33 South Ashland Avenue, Chicago, United States

Excellent

(9 reviews)

9.4

starts from

US$ 510 per one night

View hotel

Woodlawn Oasis

Holiday home

6.1 mi to the city center

6433 South Minerva Avenue, Chicago, United States

Excellent

(13 reviews)

The 3-bedroom Woodlawn Oasis Villa Chicago offers swift access to various city sites, such as Woodlawn Baptist Church, situated about a 5-minute walk away. Located a mere 1.4 km from the leading…

starts from

US$ 526 per one night

View hotel

Ace Properties

Apartment

6.3 mi to the city center

3317 North Avers Avenue, Chicago, United States

Excellent

(10 reviews)

9.8

starts from

US$ 642 per one night

View hotel

West Loop - City Views With In & Out Parking 5

Apartment

2953 ft to the city center

315 South Peoria Street, Chicago, United States

Excellent

(5 reviews)

9.4

starts from

US$ 912 per one night

View hotel

Livn West Loop Chicago Classic Queen Studio

Apartment

984 ft to the city center

555 West Jackson Boulevard, Chicago, United States

Excellent

(62 reviews)

starts from

US$ 242 per one night

View hotel

Boho Bliss - 1Br, 1Bath W/Patio!

Apartment

4.3 mi to the city center

1813 North Kedzie Avenue 3, Chicago, United States

Excellent

(36 reviews)

Boho Bliss - 1Br, 1Bath W/Patio! Apartment Chicago is situated a 5-minute walk from Chua Lien Hoa Buddhist Temple and 20 km from Chicago Midway International airport. This apartment is situated 10 km…

starts from

US$ 197 per one night

View hotel

Modern Apt W Private Entrance Washer Dryer Free Parking

Apartment

10.3 mi to the city center

2947 West Fargo Avenue, Chicago, United States

Excellent

(6 reviews)

9.2

To enjoy your vacation in Chicago, stay at the 1-room A Charming Modern Chic Basement Apartment Chicago, which is 2.6 km from the Devon Avenue and within 15 minutes' walk of the James Park. The 46 m²…

starts from

US$ 265 per one night

View hotel

Livn Millennium Park Downtown Chicago Superior 2 Br

Apartment

4265 ft to the city center

19 South Wabash Avenue, Chicago, United States

Excellent

(9 reviews)

9.2

starts from

US$ 555 per one night

View hotel

Comfy Garden Suite In Andersonville

Apartment

7.2 mi to the city center

5315 North Glenwood Avenue, Chicago, United States

Excellent

(5 reviews)

starts from

US$ 191 per one night

View hotel

Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center

2036 South Michigan Avenue Unit 306, Chicago, United States

Excellent

(10 reviews)

8.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field Chicago apartment, which is 350 metres…

starts from

US$ 442 per one night

View hotel

Lower Level Luxury

Apartment

9.2 mi to the city center

6254 W Cuyler Ave, Chicago, United States

Excellent

(10 reviews)

9.6

starts from

US$ 85 per one night

View hotel

Livn West Loop Chicago Queen Superior Studio

Apartment

Map

555 West Jackson Boulevard, Chicago, United States

Excellent

(93 reviews)

9.2

View hotel

Cozy 1Br Retreat Near Transit, Dining And Parking

Apartment

9 mi to the city center

1727 West North Shore Avenue, Chicago, United States

Excellent

(11 reviews)

9.4

starts from

US$ 144 per one night

View hotel

Charming Chicago Apt

Apartment

1.2 mi to the city center

2207 West 18Th Street, Chicago, United States

Excellent

(22 reviews)

8.4

To enjoy your vacation in Chicago, stay at Charming Chicago Apt, which is approximately 7 km from the Magnificent Mile and approximately 25 minutes' walk from the Douglas Park. The apartment is…

starts from

US$ 342 per one night

View hotel

Livn Millennium Park Downtown Chicago Superior 1Br

Apartment

4265 ft to the city center

19 South Wabash Avenue, Chicago, United States

Excellent

(15 reviews)

9.4

View hotel

Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access

Apartment

2.5 mi to the city center

1335 North Greenview Avenue 1F, Chicago, United States

Excellent

(24 reviews)

9.6

The 46 m² Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access Apartment Chicago offers easy entry to such city sights as the St. Stanislaus Kostka Church, situated nearly a 5-minute walk…

starts from

US$ 243 per one night

View hotel

Wrigley 2Br, 1Ba With Free Parking

Apartment

5.2 mi to the city center

Lakeview

Excellent

(10 reviews)

8.6

The spacious Wrigley 2Br, 1Ba With Free Parking Apartment Chicago is located 1.4 km from the Wrigley Field and a 5-minute walk from Juniper Park. This apartment is situated within 10 km of Chicago…

starts from

US$ 530 per one night

View hotel

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Hotels (124) Vacation rentals (184)

184 properties found

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Flexhome Wicker Park - Stylish 2Br - Sleeps 6
Flexhome Wicker Park - Stylish 2Br - Sleeps 6

Apartment

2.9 mi to the city center
2149 W Division St, Chicago, Il 60622, Usa, Chicago, United States

Excellent

(8 reviews)

8.4

starts from

US$ 629 per one night

View hotel
Little India Gem - Bollywood Retreat Near Markets
Little India Gem - Bollywood Retreat Near Markets

Apartment

8.9 mi to the city center
#2, 2508 West Devon Avenue, Chicago, United States

Excellent

(6 reviews)

9

View hotel
Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field
Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center
2036 South Michigan Avenue 605, Chicago, United States

Excellent

(10 reviews)

8.6

starts from

US$ 414 per one night

View hotel
Chic 2 Bedroom 1 Parking Sleeps 6
Chic 2 Bedroom 1 Parking Sleeps 6

Apartment

1.5 mi to the city center
33 South Ashland Avenue, Chicago, United States

Excellent

(9 reviews)

9.4

starts from

US$ 510 per one night

View hotel
Woodlawn Oasis
Woodlawn Oasis

Holiday home

6.1 mi to the city center
6433 South Minerva Avenue, Chicago, United States

Excellent

(13 reviews)

9

The 3-bedroom Woodlawn Oasis Villa Chicago offers swift access to various city sites, such as Woodlawn Baptist Church, situated about a 5-minute walk away. Located a mere 1.4 km from the leading…

starts from

US$ 526 per one night

View hotel
Ace Properties
Ace Properties

Apartment

6.3 mi to the city center
3317 North Avers Avenue, Chicago, United States

Excellent

(10 reviews)

9.8

starts from

US$ 642 per one night

View hotel
West Loop - City Views With In & Out Parking 5
West Loop - City Views With In & Out Parking 5

Apartment

2953 ft to the city center
315 South Peoria Street, Chicago, United States

Excellent

(5 reviews)

9.4

starts from

US$ 912 per one night

View hotel
Livn West Loop Chicago Classic Queen Studio
Livn West Loop Chicago Classic Queen Studio

Apartment

984 ft to the city center
555 West Jackson Boulevard, Chicago, United States

Excellent

(62 reviews)

9

starts from

US$ 242 per one night

View hotel
Boho Bliss - 1Br, 1Bath W/Patio!
Boho Bliss - 1Br, 1Bath W/Patio!

Apartment

4.3 mi to the city center
1813 North Kedzie Avenue 3, Chicago, United States

Excellent

(36 reviews)

9

Boho Bliss - 1Br, 1Bath W/Patio! Apartment Chicago is situated a 5-minute walk from Chua Lien Hoa Buddhist Temple and 20 km from Chicago Midway International airport. This apartment is situated 10 km…

starts from

US$ 197 per one night

View hotel
Modern Apt W Private Entrance Washer Dryer Free Parking
Modern Apt W Private Entrance Washer Dryer Free Parking

Apartment

10.3 mi to the city center
2947 West Fargo Avenue, Chicago, United States

Excellent

(6 reviews)

9.2

To enjoy your vacation in Chicago, stay at the 1-room A Charming Modern Chic Basement Apartment Chicago, which is 2.6 km from the Devon Avenue and within 15 minutes' walk of the James Park. The 46 m²…

starts from

US$ 265 per one night

View hotel
Livn Millennium Park Downtown Chicago Superior 2 Br
Livn Millennium Park Downtown Chicago Superior 2 Br

Apartment

4265 ft to the city center
19 South Wabash Avenue, Chicago, United States

Excellent

(9 reviews)

9.2

starts from

US$ 555 per one night

View hotel
Comfy Garden Suite In Andersonville
Comfy Garden Suite In Andersonville

Apartment

7.2 mi to the city center
5315 North Glenwood Avenue, Chicago, United States

Excellent

(5 reviews)

9

starts from

US$ 191 per one night

View hotel
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

Apartment

1.7 mi to the city center
2036 South Michigan Avenue Unit 306, Chicago, United States

Excellent

(10 reviews)

8.4

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field Chicago apartment, which is 350 metres…

starts from

US$ 442 per one night

View hotel
Lower Level Luxury
Lower Level Luxury

Apartment

9.2 mi to the city center
6254 W Cuyler Ave, Chicago, United States

Excellent

(10 reviews)

9.6

starts from

US$ 85 per one night

View hotel
Livn West Loop Chicago Queen Superior Studio
Livn West Loop Chicago Queen Superior Studio

Apartment

Map
555 West Jackson Boulevard, Chicago, United States

Excellent

(93 reviews)

9.2

View hotel
Cozy 1Br Retreat Near Transit, Dining And Parking
Cozy 1Br Retreat Near Transit, Dining And Parking

Apartment

9 mi to the city center
1727 West North Shore Avenue, Chicago, United States

Excellent

(11 reviews)

9.4

starts from

US$ 144 per one night

View hotel
Charming Chicago Apt
Charming Chicago Apt

Apartment

1.2 mi to the city center
2207 West 18Th Street, Chicago, United States

Excellent

(22 reviews)

8.4

To enjoy your vacation in Chicago, stay at Charming Chicago Apt, which is approximately 7 km from the Magnificent Mile and approximately 25 minutes' walk from the Douglas Park. The apartment is…

starts from

US$ 342 per one night

View hotel
Livn Millennium Park Downtown Chicago Superior 1Br
Livn Millennium Park Downtown Chicago Superior 1Br

Apartment

4265 ft to the city center
19 South Wabash Avenue, Chicago, United States

Excellent

(15 reviews)

9.4

View hotel
Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access
Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access

Apartment

2.5 mi to the city center
1335 North Greenview Avenue 1F, Chicago, United States

Excellent

(24 reviews)

9.6

The 46 m² Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access Apartment Chicago offers easy entry to such city sights as the St. Stanislaus Kostka Church, situated nearly a 5-minute walk…

starts from

US$ 243 per one night

View hotel
Wrigley 2Br, 1Ba With Free Parking
Wrigley 2Br, 1Ba With Free Parking

Apartment

5.2 mi to the city center
Lakeview

Excellent

(10 reviews)

8.6

The spacious Wrigley 2Br, 1Ba With Free Parking Apartment Chicago is located 1.4 km from the Wrigley Field and a 5-minute walk from Juniper Park. This apartment is situated within 10 km of Chicago…

starts from

US$ 530 per one night

View hotel

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