A city skyline with skyscrapers, a river, and a bridge.

Cook County Holiday Rentals

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Our top choices for Cook County holiday rentals

A rooftop terrace with a brick wall, large windows, and a metal railing.

1. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A hotel room with a bed, a view of a cityscape, and a window with curtains.

2. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is AU$470
includes taxes & fees
20 Oct - 21 Oct
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A modern bedroom with a bed, a sofa, and a hanging plant.

3. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is AU$203
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (287 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AU$379
includes taxes & fees
12 Nov - 13 Nov
The Gem Museum Suites
A modern living room with a blue sofa, a patterned rug, and a television.

5. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
Great Area Logan Square Apt Games Pets - Sleeps 5
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

6. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.0 out of 10, Wonderful, (9 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AU$447
includes taxes & fees
27 Oct - 28 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A modern building with the name 'SENIORAL' prominently displayed on the facade.

7. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is AU$241
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

8. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is AU$117
includes taxes & fees
18 Oct - 19 Oct
King Bed Non-Smoking
Lake

9. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (67 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is AU$390
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

10. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is AU$448
includes taxes & fees
1 Nov - 2 Nov
2BR Apt with 2 Baths & Laundry
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

11. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (69 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is AU$304
includes taxes & fees
2 Nov - 3 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

12. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AU$450
includes taxes & fees
27 Oct - 28 Oct
The Oak Park Loft
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

13. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is AU$364
includes taxes & fees
20 Oct - 21 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is AU$344
includes taxes & fees
26 Oct - 27 Oct
Chic Suite/Mins to L Train /Laundry/Free Parking
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

15. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Parking was free and right out front. Great apartment and the host was great with accommodations."
United States
Travis C.
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A modern bedroom with a bed, a window, and a view of an outdoor area.

16. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (26 reviews)
"We had a great time it was an awesome place and we would definitely stay there again! The host was great the place was well equipped and in a great location for us!!"
United States
Wendy T.
The price is AU$657
includes taxes & fees
20 Oct - 21 Oct
The Lincoln Square Hideaway
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

17. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A rooftop terrace with a fire pit, seating area, and a city skyline view.

18. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A modern kitchen with a large island, bar stools, and a city view.

19. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is AU$501
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
A modern living room with teal sofas, a coffee table, and a TV.

20. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is AU$233
includes taxes & fees
18 Oct - 19 Oct
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Wonderful hotel, bed are lower to the ground but really comfortable! Staff is great and the location is amazing."
Jessica 2-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Cook County

Everything you need to know about Cook County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cook County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cook County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cook County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cook County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cook County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Cook County holiday rentals we have chosen for you start as low as AU$117 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Cook County rentals

At Expedia, we put the best Cook County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cook County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cook County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cook County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.