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

Vacation Rentals in Cook County

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Our top choices for Cook County vacation 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.
The price is ￥23,561
￥57,104 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥28,501
￥56,499 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥9,975
￥22,079 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥36,577
￥41,874 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥11,147
￥49,502 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥22,674
￥26,616 total
includes taxes & fees
Nov 9 - Nov 10
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 traveler
The price is ￥10,710
￥12,918 total
includes taxes & fees
Oct 18 - Oct 19
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, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥28,343
￥43,110 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥22,168
￥46,275 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥16,072
￥33,428 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥28,088
￥49,738 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥15,992
￥40,038 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥15,248
￥37,397 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥25,176
￥74,037 total
includes taxes & fees
Oct 20 - Oct 21
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.
The price is ￥17,592
￥37,893 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥42,179
￥53,421 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥20,584
￥25,409 total
includes taxes & fees
Oct 18 - Oct 19
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"The convenience of the hotel location is key. But for what they charging PLEASE UPDATE THE HOTEL and not just the entrance."
Zeretta 1-night trip
Posted 1 hour ago
Hilton Chicago O'Hare Airport

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Vacation Apartments in Cook County

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