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Cook County Holiday Rentals

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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 HK$887
HK$1,042 total
includes taxes & fees
27 Dec - 28 Dec
Chicago luxury home suites
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop
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 HK$919
HK$1,307 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$537
HK$1,287 total
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit
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
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$537
HK$1,481 total
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,310 total
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
Private kitchen
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 HK$2,464
HK$4,526 total
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum
TV
Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
Nice 1BR Spot, Unwind & Relax
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, (42)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
The price is HK$467
HK$1,283 total
includes taxes & fees
28 Dec - 29 Dec
Clean & Equipped 1BR Apt
Fridge, microwave, oven, stovetop
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is HK$443
HK$1,543 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
10.0 out of 10, Exceptional, (43)
"Had a great stay. Great location. "
United States
Justin
The price is HK$544
HK$1,295 total
includes taxes & fees
19 Jan - 20 Jan 2026
Relaxing Chicago Studio
Fridge, microwave, oven, stovetop
Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (57)
"Super convenient if you want to see the Frank Lloyd wright house - walked to studio and train and great cafes. Perfect location "
United States
Travis S.
The price is HK$500
HK$1,507 total
includes taxes & fees
5 Jan - 6 Jan 2026
Chic Suite/Mins to L Train /Laundry/Free Parking
Fridge, microwave, oven, stovetop
Cozy, Fully Set-Up 1BR Space

Cozy, Fully Set-Up 1BR Space

Cozy, Fully Set-Up 1BR Space
Lakeview
9.4 out of 10, Exceptional, (31)
"Great place, great neighborhood "
United States
Susan A.
The price is HK$467
HK$1,283 total
includes taxes & fees
29 Dec - 30 Dec
Cozy, Fully Set-Up 1BR Space
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Rooms were clean. Easy check in. Front desk was welcoming. Very close to everything. We will book again. "
Yakshna 1-night trip
Posted 20 hours ago
The Whitehall Hotel, BW Premier Collection

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