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Search Holiday Rentals in Cook County

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Our top choices for Cook County holiday rentals

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, (405)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is ฿3,356
฿3,939 total
includes taxes & fees
28 Dec - 29 Dec
Chicago luxury home suites
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
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1022)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ฿3,672
฿5,222 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ฿10,935
฿19,365 total
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
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

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"Staff was very friendly. Walkable to restaurants and shopping. Really enjoyed the room and the ammenities. "
Amy 2-night trip
Posted 2 days ago
Silversmith Hotel Chicago Downtown

Find out more about Cook County

Vacation Apartments in Cook County

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