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Holiday Rentals in Cook County

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Our top choices for Cook County holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1006)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is €143
includes taxes & fees
14 Dec - 15 Dec
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (398)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

Kasa South Loop Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (387)
"Great apartment, great view, close to good amenities, very safe."
United Kingdom
Ian
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
6.0 out of 10, (4)
"They’re rude and unprofessional. I understand my mistakes but them fully not communicating afterwards and canceling my reservation is wild "
United States
Anthony
The price is €135
includes taxes & fees
14 Dec - 15 Dec
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy
4.0 star property
Near West Side
9.6 out of 10, Exceptional, (224)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is €87
includes taxes & fees
16 Dec - 17 Dec
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen
The Gem Museum Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is €177
includes taxes & fees
14 Dec - 15 Dec
The Gem Museum Suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt
Lakeview
9.0 out of 10, Wonderful, (41)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
The price is €144
includes taxes & fees
15 Dec - 16 Dec
Clean & Equipped 1BR Apt
Comfort Double Room
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
3.8 out of 10, (67)
"Good "
United States
Abel
The price is €81
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO
West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview 2BR Apartment
Lakeview
9.2 out of 10, Wonderful, (27)
"Great place and area!"
United States
Thomas J.
The price is €157
includes taxes & fees
14 Dec - 15 Dec
Lakeview 2BR Apartment
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is €180
includes taxes & fees
16 Dec - 17 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
Stylish Apartment near Chicago Downtown
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Near West Side
10.0 out of 10, Exceptional, (270)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (6)
"Great place. Very comfortable & really nice location- loved the corner coffee shop "
United States
Sandra
Modern West Loop Gem-City Views & Prime Location 6
Smart TV, fireplace, printers
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Lakeview
10.0 out of 10, Exceptional, (111)
"Got together for a friends reunion in Chicago. The property was perfect and had all the extras in place to make it feel like a home for a few days. I would definitely stay again and highly recommend. "
United States
Jason M.
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Interior
Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!
East Garfield Park
7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!
Interior
Art Villa

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
Art Villa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cook County Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great place always. "
Robert 1-night trip
Posted 18 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Cook County

Holiday Homes in Cook County

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