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

Vacation Rentals in Cook County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥14,058
￥46,282 total
includes taxes & fees
Oct 12 - Oct 13
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 ￥11,398
￥36,463 total
includes taxes & fees
Oct 12 - Oct 13
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 and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is ￥9,974
￥22,075 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, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ￥39,894
￥45,671 total
includes taxes & fees
Nov 9 - Nov 10
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.
The price is ￥11,240
￥34,455 total
includes taxes & fees
Oct 12 - Oct 13
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
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is ￥11,145
￥49,293 total
includes taxes & fees
Oct 13 - Oct 14
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, (1,367 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥24,696
￥28,990 total
includes taxes & fees
Nov 10 - Nov 11
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 12 - Oct 13
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, (63 reviews)
"Location is perfect"
United States
Mary
The price is ￥28,337
￥43,102 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 ￥15,198
￥36,936 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, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is ￥19,765
￥37,692 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥17,224
￥37,298 total
includes taxes & fees
Oct 28 - Oct 29
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
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is ￥15,989
￥40,030 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, (72 reviews)
"Easy access to the Green Line."
United States
Michael
The price is ￥16,148
￥37,517 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥10,716
￥28,570 total
includes taxes & fees
Oct 12 - Oct 13
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 ￥23,588
￥71,882 total
includes taxes & fees
Oct 14 - Oct 15
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, (34 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.
The price is ￥10,871
￥28,736 total
includes taxes & fees
Oct 14 - Oct 15
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 ￥18,111
￥37,507 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, (540 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ￥43,874
￥55,409 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥20,580
￥25,404 total
includes taxes & fees
Oct 14 - Oct 15
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cook County Hotel Reviews

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Since Our flight kept being delayed; we arrived very early next day. We notified the front desk when this was happening. Upon our arrival, we were greeted with a friendly front desk person. Our room was ready. The room was spacious. It was beautiful. Staff in the front desk were very friendly and helpful."
Jacqueline 2-night trip
Posted 12 hours ago
Sports Illustrated Resorts Chicago

Find out more about Cook County

Vacation Apartments in Cook County

Search for Vacation rentals in Cook County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Cook County using one of the methods below:

  • View our selection of featured Vacation rentals in Cook County
  • Use the map to find apartments and other Vacation homes in the Cook County neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Cook County while they last

Look no further and take a look at our great range of rental properties in Cook County!