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Cook County Holiday Rentals

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Our top choices for Cook County holiday rentals

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (53 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is HK$932
HK$1,094 total
includes taxes & fees
16 Nov - 17 Nov
Wrigleyville Suites

2. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is HK$588
HK$2,048 total
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

3. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is HK$796
HK$3,352 total
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking

4. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (94 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is HK$1,193
HK$1,884 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago

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 HK$471
HK$1,515 total
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5

6. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is HK$716
HK$2,544 total
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish

7. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is HK$596
HK$1,285 total
includes taxes & fees
23 Nov - 24 Nov
Hyde Park Trendy Studio Apartment in Good Spot

8. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (310 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is HK$1,569
HK$1,796 total
includes taxes & fees
16 Nov - 17 Nov
The Gem Museum Suites

9. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 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 HK$565
HK$1,026 total
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago

10. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is HK$588
HK$2,048 total
includes taxes & fees
17 Nov - 18 Nov
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

11. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is HK$482
HK$584 total
includes taxes & fees
1 Dec - 2 Dec
King Bed Non-Smoking

12. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (564 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is HK$1,342
HK$1,768 total
includes taxes & fees
22 Nov - 23 Nov
Level Chicago – Old Town

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, (25 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 HK$824
HK$1,914 total
includes taxes & fees
18 Nov - 19 Nov
3BR Complete and Spacious Apartment in Ideal Spot

14. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (14 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is HK$494
HK$1,244 total
includes taxes & fees
17 Nov - 18 Nov
1BR/1BA City Comfort

15. 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, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is HK$579
HK$1,507 total
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking

16. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is HK$648
HK$2,446 total
includes taxes & fees
16 Nov - 17 Nov
Sleeps 7 • Huge Projector • Designated Workspace

17. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,416 reviews)
"Great for extended stays."
United States
Jeff
The price is HK$1,500
HK$1,761 total
includes taxes & fees
13 Dec - 14 Dec
Sentral Michigan Avenue

18. 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.
The price is HK$563
HK$1,383 total
includes taxes & fees
17 Nov - 18 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

19. Peaceful Zen Flat | 2BR Oasis with Free Parking

Peaceful Zen Flat | 2BR Oasis with Free Parking
West Town
10.0 out of 10, Exceptional, (8 reviews)
"Awesome place to stay, no issues with anything whatsoever and will definitely love to come back!"
United States
joey d.
The price is HK$1,085
HK$3,584 total
includes taxes & fees
1 Dec - 2 Dec
Peaceful Zen Flat | 2BR Oasis with Free Parking

20. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is HK$484
HK$2,870 total
includes taxes & fees
16 Nov - 17 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
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