Cook County Holiday Rentals

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Top Holiday Rentals Destinations in Cook County

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (388)
"Likes having a kitchen and living room"
The price is AU$289
includes taxes & fees
2 May - 3 May
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.0 out of 10, Very good, (74)
"The property was nice, clean and fresh. The Studio was really nice and updated. "
The price is AU$194
includes taxes & fees
5 May - 6 May
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (294)
"The train was loud, but not intolerable. Parking is very limited especially on Saturday. Overall would say here again !"
The price is AU$317
includes taxes & fees
28 May - 29 May
Sonder South Wabash
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Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (46)
"Sonders are always clean and efficient and this one was that, but this one isn't the best. Units in the Burnham are renovated but they have old ceilings made of wood which do not prevent noise transfer. They gave me a unit on the second floor and I could hear almost everything the person above me said or did. Sometimes when that person walked, the glasses in my unit slightly vibrated and you'd hear clinking. "
The price is AU$352
includes taxes & fees
5 May - 6 May
Sonder The Burnham
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (123)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is AU$373
includes taxes & fees
27 May - 28 May
Found Chicago powered by Sonder
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (23)
"Great new, contemporary facility. Will absolutely recommend."
The price is AU$374
includes taxes & fees
6 May - 7 May
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (206)
"Nice"
The price is AU$602
includes taxes & fees
2 May - 3 May
Level Chicago – Old Town
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (97)
"The only real problem is train noise I was lucky that my unit was at the end of hallway so relatively far from train noise but they moved us for one night to another unit because of plumbing issue and as extremely noisy "
The price is AU$320
includes taxes & fees
28 May - 29 May
Sonder Jewelers Row
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (65)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is AU$430
includes taxes & fees
27 May - 28 May
Sonder The Plymouth
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is AU$270
includes taxes & fees
2 May - 3 May
Your Home Away From Home
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (160)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (7)
"Great little home away from home. Definitely need to be painted and maintenance upgrades need to be addressed but other than that we had a great time"
The price is AU$279
includes taxes & fees
9 May - 10 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is AU$326
includes taxes & fees
28 May - 29 May
Sonder The Opal
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (17)
"Great apartment! Perfect for 2 adults and 2 teens. Extremely close to Blue Line into Chicago. Easy drive to Wheaton (could have easily taken the Metra instead). Recommend Cuzzo pizza and Addis Cafe in Oak Park. One of us came down with a cold- grocery and drugstore nearby, and we spent the day playing cards and watching movies. Kitchenette was great for making our own (read: cheap) breakfasts each day. Thank you!"
Cozy modern unit w/ easy access to downtown Chi
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (6)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is AU$266
includes taxes & fees
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (15)
"My wife and I spent a long weekend here. The apartment had plenty of room, was nicely decorated. The kitchen contained everything we needed to cook a full meal (which we did not). The bed is very comfortable. Ride service to downtown averaged $25. It was perfect."
The price is AU$300
includes taxes & fees
3 May - 4 May
Chic Suite/Mins to L Train /Laundry/Free Parking
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is AU$540
includes taxes & fees
5 May - 6 May
national historic home near downtown airports no parties no events
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
10.0 out of 10, Exceptional, (2)
"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
Spacious Family Glenwood Estates Home w/ Hot Tub!
9.4 out of 10, Exceptional, (13)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!
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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.

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$194 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. 

Cook County Holiday Home Travel Info

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