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Top Holiday Rentals in Oak Park

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"We stayed stayed at the Sentral for a business/family trip. This hotel is beautiful and accommodating. Sandra at the front desk was the sweetest and made check in a breeze, even allowing us to check in early. The room was clean, however there was a burn mark on the kitchen floor and it appeared as it was not vacuumed. Otherwise the room was wonderful, we would definitely stay here again! "
The price is ฿3,720
฿5,379 total
includes taxes & fees
25 Nov - 26 Nov
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is ฿1,951
฿2,290 total
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is ฿4,161
฿4,885 total
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is ฿6,057
฿7,697 total
includes taxes & fees
24 Nov - 25 Nov
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is ฿4,003
฿4,700 total
includes taxes & fees
17 Dec - 18 Dec
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"Very convenient location, the apartment was impeccable "
The price is ฿4,828
฿5,667 total
includes taxes & fees
23 Dec - 24 Dec
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is ฿4,727
฿5,549 total
includes taxes & fees
23 Dec - 24 Dec
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is ฿2,963
฿3,479 total
includes taxes & fees
8 Dec - 9 Dec
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is ฿3,884
฿4,560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is ฿4,421
฿5,190 total
includes taxes & fees
23 Dec - 24 Dec
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is ฿5,464
฿6,414 total
includes taxes & fees
17 Dec - 18 Dec
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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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Other types of properties in Oak Park you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8199)
"I thought the staff was really helpful. I wasn’t a fan of the parking situation but the garage next door was nice to deal with. They just kept calling with stipulations like you can’t come and go with the car easily and because of concerts we wouldn’t have access at times, that kind of thing. It was convenient for transportation, walking, food and other conveniences which was nice. The room was really nice but the air conditioning/heat kept getting stuck on high blast and was too warm for our...
The price is ฿4,447
฿5,220 total
includes taxes & fees
24 Nov - 25 Nov
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3569)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."
The price is ฿3,466
฿4,068 total
includes taxes & fees
23 Dec - 24 Dec
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Suite, 1 Queen Bed, Kitchenette | Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3297)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
The price is ฿3,339
฿3,919 total
includes taxes & fees
23 Dec - 24 Dec
Club Quarters Hotel, Central Loop, Chicago
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.

Frequently asked questions

Are there holiday rentals in Oak Park?

Yes, there are holiday rentals in Oak Park close to Oak Park Conservatory, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

How many holiday rentals are there in Oak Park?

With 26 Expedia holiday rentals, you're guaranteed to find just the right place for your Oak Park stay.

What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

What’s a holiday rental in Oak Park like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Park. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.