Oak Park Holiday Rentals

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Check prices for these dates

Tonight
4 Nov - 5 Nov
Tomorrow
5 Nov - 6 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Oak Park

Exterior
Historic Oak Park Residence
Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"It was very spacious. The kids had a great time. I love having a washer and dryer to use due to having alot of kids"
United States
Makita
The price is HK$1,082
HK$2,102 total
includes taxes & fees
20 Nov - 21 Nov
Historic Oak Park Residence
Interior
Historic Oak Park Home
Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is HK$1,202
HK$2,239 total
includes taxes & fees
16 Nov - 17 Nov
Historic Oak Park Home
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (972)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$1,042
HK$1,451 total
includes taxes & fees
25 Nov - 26 Nov
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (604)
"Great place close to downtown. Well equipped and super clean. "
United States
Mauricio
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (375)
"Great place to stay. Loved it!"
United States
Peter
The price is HK$1,601
HK$2,053 total
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (397)
"Quite and low key spot"
United States
Shunica
The price is HK$786
HK$923 total
includes taxes & fees
19 Nov - 20 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (249)
"Great stay. "
United States
Teresa
The price is HK$984
HK$1,155 total
includes taxes & fees
2 Dec - 3 Dec
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (706)
"Location was nice."
United States
Juliet
The price is HK$1,050
HK$1,233 total
includes taxes & fees
24 Nov - 25 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (369)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (215)
"excellent room, beds - great communication and very stylish- only issue is parking can be complicated "
United States
chris
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (56)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
United States
Swastika
The price is HK$918
HK$1,078 total
includes taxes & fees
3 Dec - 4 Dec
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (187)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is HK$852
HK$1,000 total
includes taxes & fees
24 Nov - 25 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is HK$616
HK$723 total
includes taxes & fees
5 Nov - 6 Nov
Wrigleyville Suites
Private kitchen
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (94)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is HK$1,399
HK$1,602 total
includes taxes & fees
11 Nov - 12 Nov
The Gem Museum Suites
Living room
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"I enjoyed my stay! Thanks!"
United States
Jonathan
The price is HK$918
HK$1,078 total
includes taxes & fees
24 Nov - 25 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is HK$1,886
HK$3,017 total
includes taxes & fees
2 Dec - 3 Dec
Stylish Apartment near Chicago Downtown
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
9.4 out of 10, Exceptional, (33)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
United States
Camron K.
The price is HK$490
HK$1,309 total
includes taxes & fees
2 Dec - 3 Dec
Clean & Equipped 1BR Apt
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (9)
"Good communication and easy check-in"
United States
Chen
The price is HK$536
HK$1,286 total
includes taxes & fees
10 Nov - 11 Nov
Cozy Studio in Hyde Park-Walk to Lake & University
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (29)
"Everything was pristine and comfortable. I highly recommend this place. "
United States
Joyce
The price is HK$505
HK$1,247 total
includes taxes & fees
11 Nov - 12 Nov
Relaxing Chicago Studio
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 Oak Park Hotel Reviews

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Male staff members were nice and helpful. The full bar was great. The interior was stylish, and I loved the fireplace with its cozy atmosphere. I stayed here for 1 week."
Chloe 6-night trip
Posted 1 day ago
Aloft Chicago Mag Mile

Find out more about Oak Park

Search for holiday rentals in Oak Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Park using one of the methods below:

  • View our selection of featured holiday rentals in Oak Park
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  • Enter your travel dates to view the best deals on holiday rentals in Oak Park while they last

Look no further and take a look at our great range of rental properties in Oak Park!

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.

What are some of the best holiday rentals that Oak Park has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Oak Park offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Oak Park?

With 29 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.