Chicago holiday rentals

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2025-09-15
2025-09-16

Maximum period that can be booked is 30 days. Please enter alternative dates.

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2025-09-15
2025-09-16

Maximum period that can be booked is 30 days. Please enter alternative dates.

Ages of children:
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Lowest price
City centre
5-star hotels
Highest rating
Free Wi-Fi
9.4
Excellent
Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub
Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

Excellent
8 reviews
9.4
3742 N. Keeler Avenue, Chicago,, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 9.9 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Jacuzzi
Children's play area
Air conditioning
No pets allowed
Situated within a 15-minute drive of Wrigley Field, the 2-bedroom Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub features a terrace with views of the garden. Offering…
9.6
Excellent
4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome
4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

Excellent
5 reviews
9.6
329 West Schiller Street, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Beach access
Fitness centre
Tennis court
Golf course
Hiking
Spa lounge
4 Bedroom In Best Location Parking Fireplace Back Yard Home Office Pets Welcome is nestled a stroll from Lincoln Park and offers live performances to make your visit more entertaining. The 4-bedroom…
9
Excellent
Old Town 3Bd 3Ba Coach House, Garage Parking Incl
Old Town 3Bd 3Ba Coach House, Garage Parking Incl

Old Town 3Bd 3Ba Coach House, Garage Parking Incl

Excellent
1 review
9
1435 N Mohawk Ch, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Old Town 3Bd 3Ba Coach House, Garage Parking Incl Home Chicago provides easy access to various city attractions, such as The Noble Horse Theatre, situated a 6-minute walk away.
9.2
Excellent
New Modern 3Br, Gym, Workspace, Quiet Location
New Modern 3Br, Gym, Workspace, Quiet Location

New Modern 3Br, Gym, Workspace, Quiet Location

Excellent
3 reviews
9.2
3656 N Osage Ave Unit 3, Chicago, Il 60634, Usa, Chicago, United States
Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
24-hour reception
Fitness centre
Jacuzzi
Air conditioning
Pets allowed
The 2-bedroom New Modern 3Br, Gym, Workspace, Quiet Location is located about 10 minutes by car from Harlem-Irving Plaza Shopping Center and provides guests with a hot tub for a more relaxing stay.
10
Excellent
Perfect Location Across From Park & Train Station
Perfect Location Across From Park & Train Station

Perfect Location Across From Park & Train Station

Excellent
2 reviews
10
244 North Hamlin Avenue, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
Pets allowed
The 4-bedroom Perfect Location Across From Park & Train Station Villa Chicago offers easy access to such tourist spots as Midwest Athletic Club, located only a 6-minute walk away.
9.2
Excellent
Boutique Garden House Chicago 3-Story Sleeps 12
Boutique Garden House Chicago 3-Story Sleeps 12

Boutique Garden House Chicago 3-Story Sleeps 12

Excellent
3 reviews
9.2
7131 South Michigan Avenue, Chicago, United States
Superb location
This property boasts superb location. It has a score 8.3 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Situated around 400 metres from First Progressive Church of Christ, the 4-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 offers quick access to numerous city landmarks nearby.
10
Excellent
Personal Gym Luxury Balcony Condo
Personal Gym Luxury Balcony Condo

Personal Gym Luxury Balcony Condo

Excellent
1 review
10
5105 N East River Rd Unit 3F, Chicago, Il 60656, Usa, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
24-hour reception
Air conditioning
Pets allowed
Personal Gym Luxury Balcony Condo villa offers swift access to various city sites, such as St. Joseph the Betrothed Ukranian Catholic Church, situated 5 minutes' walk away.
10
Excellent
Gorgeous 5 Bedroom Gem With Games
Gorgeous 5 Bedroom Gem With Games

Gorgeous 5 Bedroom Gem With Games

Excellent
1 review
10
7928 South Ada Street, Chicago, United States
Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
Fitness centre
Billiard tables
Table tennis
Game room
Video games
Air conditioning
Pets allowed
During the stay at Gorgeous 5 Bedroom Gem With Games villa, guests can indulge in ping-pong and pool or visit the Frederick C. Frank Lloyd Wright's Robie House, located about 7 km away.
9.8
Excellent
Historic Luxury Townhouse In Downtown Chicago
Historic Luxury Townhouse In Downtown Chicago

Historic Luxury Townhouse In Downtown Chicago

Excellent
7 reviews
9.8
71 East Bellevue Place The Townhouse, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Cots
Air conditioning
Pets allowed
Offering garden views, Historic Luxury Townhouse In Downtown Chicago Villa is situated at a distance of 500 metres from 360 Chicago Observation Deck.
8
Good
Woodlawn Oasis
Woodlawn Oasis

Woodlawn Oasis

Good
3 reviews
8
6433 South Minerva Avenue, Chicago, United States
Excellent location
This property boasts excellent location. It has a score 9.1 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Located within 400 metres of Woodlawn Baptist Church, the 3-bedroom Woodlawn Oasis villa gives easy access to various tourist attractions in the area. Providing guests with Wi-Fi and a car park, the…
9
Excellent
Roscoe Village Family Hideaway
Roscoe Village Family Hideaway

Roscoe Village Family Hideaway

Excellent
1 review
9
1811 West Eddy Street, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Air conditioning
No pets allowed
Situated about 25 minutes' walk from Fellger Park, Roscoe Village Family Hideaway invites guests to relax at a sunny patio.
10
Excellent
Stylish Chicago Retreat Walk To Loyola University
Stylish Chicago Retreat Walk To Loyola University

Stylish Chicago Retreat Walk To Loyola University

Excellent
1 review
10
6242 N Kenmore Ave Unit D, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
Beach access
Cots
Pets allowed
Nestled within 25 minutes' walk of Jarvis Beach Park, Stylish Chicago Retreat, Walk To Loyola University entices guests to explore various tourist destinations nearby.
7
Good
Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck
Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck

Good
1 review
7
67 East Cedar Street, Chicago, United States
Exceptional location
This property boasts exceptional location. It has a score 10 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Beach access
Cots
Children's play area
Air conditioning
Pets allowed
Located 8 minutes' walk from Holy Name Cathedral, Spectacular Gilded Age 6 Bedroom Gold Coast Mansion With Deck Chicago villa gives access to various tourist sites in the vicinity.
Trendy Wicker Park Loft With Parking
Trendy Wicker Park Loft With Parking

Trendy Wicker Park Loft With Parking

1554 N Ashland Ave, Chicago, United States
Wi-Fi
Pets allowed
Along with Wi-Fi and parking, the 2-bedroom Trendy Wicker Park Loft With Parking Villa offers proximity to Willis Tower, located about 10 minutes away by car.
The Urban Manor By Luxuri365
The Urban Manor By Luxuri365

The Urban Manor By Luxuri365

4339 South Evans Avenue Unit 1, Chicago, United States
Featuring parking, 3-bedroom The Urban Manor By Luxuri365 Villa is located in the Bronzeville district and within 7 km of such cultural tourist attractions as The Art Institute of Chicago. Guests can…
Frank Lloyd Wright'S Emil Bach House
Frank Lloyd Wright'S Emil Bach House

Frank Lloyd Wright'S Emil Bach House

7415 North Sheridan Road, Chicago, United States
Wi-Fi
Frank Lloyd Wright'S Emil Bach House Hotel offers proximity to such city sites as Leone Park, located nearly 5 minutes' drive away.
Main House At Cherry Street 4Bdr
Main House At Cherry Street 4Bdr

Main House At Cherry Street 4Bdr

1519 South Saint Louis Avenue, Chicago, United States
Wi-Fi in rooms
Free Wi-Fi
Air conditioning
Main House At Cherry Street 4Bdr Chicago villa offers swift access to various city sites, such as Mt. Hebron Missionary Baptist Church, situated approximately 5 minutes' walk away.
Huge Projector And Designated Workspace, Near Wrigley
Huge Projector And Designated Workspace, Near Wrigley

Huge Projector And Designated Workspace, Near Wrigley

3116 W Waveland Ave, Unit 2B, Chicago, Il 60618, Usa, Chicago, United States
Pleasant location
This property boasts pleasant location. It has a score 0 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Free Wi-Fi
24-hour reception
Air conditioning
Pets allowed
Nestled a 10-minute ride from Andersonville, Huge Projector And Designated Workspace, Near Wrigley Chicago villa entices guests to explore various tourist destinations nearby.
Central Chicago Suite Access To Patio Suite 1
Central Chicago Suite Access To Patio Suite 1

Central Chicago Suite Access To Patio Suite 1

1220 West Augusta Boulevard, Chicago, United States
Very good location
This property boasts very good location. It has a score 7.5 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Wi-Fi in rooms
Wi-Fi
The 1-bedroom Central Chicago Suite Access To Patio Suite 1 offers swift access to various city sites, such as Polish Museum of America, situated approximately a 5-minute walk away. Located at a…
3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome
3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome

3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome

1426 North North Park Avenue, Chicago, United States
Pleasant location
This property boasts pleasant location. It has a score 0 out of 10 for location according to the visitors’ reviews. It must be a convenient place to stay!
Free Wi-Fi
Express check-in/ -out
Beach access
Cots
Air conditioning
Pets allowed
Spacious Home For Group Or Family In Old Town; Walk To Everything, Back Yard, Parking is situated in Old Town district of Chicago, occupies the area of 223 m² and has a balcony. The accommodation…

All hotels in Chicago are booked for your dates. Try other dates

2025-09-15
2025-09-16

Maximum period that can be booked is 30 days. Please enter alternative dates.

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