Oak Park Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Oak Park

At Home in Oak Park
Terrace/patio

At Home in Oak Park

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is S$406
includes taxes & fees
26 Oct - 27 Oct
At Home in Oak Park
Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (938)
"The staff was extremely helpful and the rooms are clean with a beautiful view of downtown and the lake. I will definitely stay here again. "
The price is S$333
includes taxes & fees
5 Oct - 6 Oct
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, (537)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (358)
"Great place to stay. Loved it!"
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (371)
"Great stay!"
The price is S$205
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (231)
"Great location and lovely amenities. "
The price is S$282
includes taxes & fees
26 Oct - 27 Oct
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (354)
"It was a really nice and secure property. "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (665)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is S$302
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (205)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (51)
"Place was in a great location close to good restaurants "
The price is S$256
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
Kasa River North Chicago
The Gem Museum Suites
Private kitchen

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is S$330
includes taxes & fees
8 Oct - 9 Oct
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is S$188
includes taxes & fees
1 Oct - 2 Oct
Wrigleyville Suites
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (180)
"Great location!!!"
The price is S$271
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Stylish Apartment near Chicago Downtown
Private kitchen

Stylish Apartment near Chicago Downtown

2.0 star property
The price is S$324
includes taxes & fees
30 Sept - 1 Oct
Stylish Apartment near Chicago Downtown
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (138)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is S$321
includes taxes & fees
20 Oct - 21 Oct
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (64)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is S$347
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is S$164
includes taxes & fees
30 Sept - 1 Oct
Ground Floor Studios in Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
Private kitchen

River West, Third Floor Chicago by 747 Lofts

2.0 star property
9.0 out of 10, Wonderful, (16)
"Overall solid property, I will return."
The price is S$334
includes taxes & fees
9 Oct - 10 Oct
River West, Third Floor 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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Top Oak Park Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Loved this hotel. The room was very small but didn’t bother me because we are only in there to sleep anyways. The location was perfect, walking distance to so much! Would definitely stay again! "
Stephanie 2-night trip
Posted 7 hours ago
citizenM Chicago Downtown

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 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.