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Check prices for these dates

Tonight
24 Jan - 25 Jan
Tomorrow
25 Jan - 26 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Top Holiday Rentals in Oak Park

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (662)
"I loved the apartment like hotel rooms. The decor and special touches were really nice! Location and pricing was also great!I just wish they had more elevators, with so many floors elevator waits were a little long. The staff was great as well and answered everything throughly that I needed. Will definitely be back "
The price is ฿3,719
฿5,361 total
includes taxes & fees
2 Feb - 3 Feb
Sentral Michigan Avenue
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, (420)
"Great place to spend a few days. "
The price is ฿3,361
฿3,946 total
includes taxes & fees
28 Jan - 29 Jan
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (245)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is ฿2,018
฿2,369 total
includes taxes & fees
17 Feb - 18 Feb
Sonder Market Hall
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, (353)
"Great property. Quick check in and in great location. Will definitely come back "
Kasa Magnificent Mile Chicago
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (133)
"If you are a walker and just want to explore what Chicago has to offer please book this place. You can store your bags before and after checkin/out and the lobby is so nice and quiet. "
The price is ฿4,270
฿5,013 total
includes taxes & fees
9 Feb - 10 Feb
Sonder The Burnham Apartments
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (285)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is ฿5,653
฿7,395 total
includes taxes & fees
28 Jan - 29 Jan
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, (183)
"It was a Great option, straight and contactless."
The price is ฿4,094
฿4,806 total
includes taxes & fees
24 Feb - 25 Feb
Found Chicago powered by Sonder
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, (123)
"This property was so clean and safe with so many options to eat parking was easy with the parking app. I cannot wait to stay here again. I was at peace. No one was loud or obnoxious. It was perfect if you’re second-guessing this property don’t it’s so convenient and very easy to check in and out of Little Italy was the best. Thank you for such a great experience. Oh, and the heater above the door as you walk in is amazing as well. Lol"
The Neighborhood Hotel-Little Italy
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is ฿3,486
฿4,092 total
includes taxes & fees
18 Feb - 19 Feb
Sonder Jewelers Row
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, (251)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (118)
"It was nice, comfortable and close to everything downtown."
The price is ฿2,843
฿3,337 total
includes taxes & fees
30 Jan - 31 Jan
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (88)
"Loved the location. "
The price is ฿3,506
฿4,116 total
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is ฿4,200
฿4,931 total
includes taxes & fees
9 Feb - 10 Feb
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, (36)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is ฿4,541
฿5,331 total
includes taxes & fees
24 Feb - 25 Feb
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
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
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8430)
"Good customer service and very clean"
The price is ฿3,150
฿3,698 total
includes taxes & fees
28 Jan - 29 Jan
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3725)
"Enjoyed our stay. The hotel is a no frills hotel but the location is hard to beat right on the river. Our room had a fantastic view and was clean. We stayed two nights and both days housekeeping came around and refreshed towels and cleaned up. Overall we would come back to the River Hotel."
The price is ฿2,594
฿3,046 total
includes taxes & fees
23 Feb - 24 Feb
River Hotel
Eurostars Magnificent Mile
Lobby lounge

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2818)
"The hotel was very clean and the staff was very friendly "
The price is ฿2,930
฿3,440 total
includes taxes & fees
23 Feb - 24 Feb
Eurostars Magnificent Mile
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 30 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 Mills Park and Oak Park Conservatory are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Michigan Avenue and Wrigley Field.

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.