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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, (628)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is ฿3,758
฿5,417 total
includes taxes & fees
2 Jan - 3 Jan 2025
Sentral Michigan Avenue
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, (342)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
Kasa Magnificent Mile Chicago
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, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is ฿4,257
฿4,997 total
includes taxes & fees
13 Jan - 14 Jan 2025
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (228)
"Very nice place for the cost. Could hear outside and inside noises but noise doesn’t bother me. Would stay here again."
The price is ฿1,812
฿2,127 total
includes taxes & fees
21 Jan - 22 Jan 2025
Sonder Market Hall
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is ฿6,059
฿7,797 total
includes taxes & fees
4 Jan - 5 Jan 2025
Level Chicago – Old Town
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, (248)
"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, (110)
"Great stay overall"
The price is ฿4,248
฿4,987 total
includes taxes & fees
1 Jan - 2 Jan 2025
Kasa River North Chicago
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (122)
"Very nice place, good location near sights and bus central station, a bit slow with the heating, but overall a very good value."
The price is ฿4,303
฿5,051 total
includes taxes & fees
23 Jan - 24 Jan 2025
Sonder The Burnham Apartments
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (179)
"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 ฿4,138
฿4,857 total
includes taxes & fees
23 Jan - 24 Jan 2025
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, (111)
"Absolutely loved loved loved my stay here!! It feels more like a personal home rather than a hotel. It’s very private, has tons of space, and felt very safe. "
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 ฿3,515
฿4,126 total
includes taxes & fees
13 Jan - 14 Jan 2025
Sonder Jewelers Row
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (87)
"Loved the location. "
The price is ฿3,544
฿4,160 total
includes taxes & fees
23 Jan - 24 Jan 2025
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 ฿3,846
฿4,515 total
includes taxes & fees
16 Jan - 17 Jan 2025
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 ฿4,319
฿5,071 total
includes taxes & fees
14 Jan - 15 Jan 2025
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)
"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
Exterior

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8280)
"Wallpaper in lobby is old. No working ice machines to be found."
The price is ฿3,578
฿4,200 total
includes taxes & fees
1 Jan - 2 Jan 2025
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3625)
"Having to park my car 4 blocks away"
The price is ฿3,564
฿4,184 total
includes taxes & fees
19 Jan - 20 Jan 2025
River Hotel
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3105)
"We were upgraded to a room with a view of the river wh"
The price is ฿5,058
฿6,944 total
includes taxes & fees
19 Jan - 20 Jan 2025
Hyatt Regency 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 27 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 Madison Street Theatre and Ernest Hemingway Museum and House, 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.