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Vacation Rentals in Cook County

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Top Cities in Cook County

Our top choices for Cook County vacation rentals

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (405)
"Great location, clean room and friendly staff!"
United States
Scott
$202 nightly
The price is $237
Dec 28 - Dec 29
Total with taxes and fees
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
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
$132 nightly
The price is $156
Dec 28 - Dec 29
Total with taxes and fees
Chicago luxury home suites

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
$219 nightly
The price is $257
Jan 9 - Jan 10, 2026
Total with taxes and fees
Kasa River North Chicago

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1021)
"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
$143 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sentral Michigan Avenue

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
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
$149 nightly
The price is $166
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
9.6 out of 10, Exceptional, (15)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$174 nightly
The price is $191
Jan 1 - Jan 2, 2026
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$153 nightly
The price is $168
Jan 7 - Jan 8, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
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.
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
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
$507 nightly
The price is $596
Dec 30 - Dec 31
Total with taxes and fees
ENVITAE Hotel 4 Bedroom Luxury Apartments

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
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 traveler
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Complete 1BR Home Sum
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Complete 1BR Home Sum

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax

Apartment in Lakeview

Clean & Equipped 1BR Apt
9.0 out of 10, Wonderful, (42)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
$150 nightly
The price is $165
Dec 28 - Dec 29
Total with taxes and fees
Clean & Equipped 1BR Apt
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
$177 nightly
The price is $198
Dec 29 - Dec 30
Total with taxes and fees
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (43)
"Had a great stay. Great location. "
United States
Justin
$135 nightly
The price is $167
Jan 19 - Jan 20, 2026
Total with taxes and fees
Relaxing Chicago Studio
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.
$169 nightly
The price is $194
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking

Apartment in Lakeview

Cozy, Fully Set-Up 1BR Space
9.4 out of 10, Exceptional, (31)
"Great place, great neighborhood "
United States
Susan A.
$150 nightly
The price is $165
Dec 29 - Dec 30
Total with taxes and fees
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

Find out more about Cook County

Discover your perfect Cook County vacation rental with Expedia

How many vacation rentals are available in Cook County?


Expedia has plenty of vacation rentals to choose from in and around  Cook County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Cook County?


The selection of Cook County vacation rentals we have selected for you start as low as $96 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Cook County?


Vacation rentals in Cook County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Cook County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Cook County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Cook County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Cook County?


Find vacation rentals in Cook County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Cook County.  


What amenities are available in a vacation rental in Cook County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Cook County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Cook County?   


Everytime is a great time to head to Cook County! Staying in a Cook County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Cook County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Cook County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Cook County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Cook County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.