Oak Park Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
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Jan 23 - Jan 25

Vacation 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 P8,539
P15,388 total
includes taxes & fees
Nov 2 - Nov 3
At Home in Oak Park
Historic Oak Park Home
Interior

Historic Oak Park Home

2.0 star property
10.0 out of 10, Exceptional, (4)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
The price is P8,055
P15,647 total
includes taxes & fees
Nov 2 - Nov 3
Historic Oak Park Home
Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (948)
"Near everything great amenities "
The price is P8,805
P12,034 total
includes taxes & fees
Oct 5 - Oct 6
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, (545)
"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, (361)
"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, (374)
"Great stay!"
The price is P7,329
P8,604 total
includes taxes & fees
Nov 2 - Nov 3
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, (235)
"Great location and lovely amenities. "
The price is P8,313
P9,759 total
includes taxes & fees
Nov 2 - Nov 3
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, (355)
"nice area, shops nearby"
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, (675)
"great room, clean good space and close to places "
The price is P8,805
P10,336 total
includes taxes & fees
Oct 22 - Oct 23
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, (207)
"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, (53)
"Place was in a great location close to good restaurants "
The price is P8,805
P10,336 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

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 P12,083
P13,833 total
includes taxes & fees
Oct 28 - Oct 29
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 P4,497
P8,185 total
includes taxes & fees
Oct 5 - Oct 6
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, (181)
"Great location!!!"
The price is P8,313
P9,759 total
includes taxes & fees
Nov 2 - Nov 3
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 P11,516
P19,972 total
includes taxes & fees
Oct 5 - Oct 6
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
7.6 out of 10, Good, (139)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
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)
" "
The price is P15,193
P37,066 total
includes taxes & fees
Oct 14 - Oct 15
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, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is P10,937
P12,839 total
includes taxes & fees
Oct 5 - Oct 6
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Iron/ironing board, free WiFi

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. "
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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Top Oak Park Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Everything good "
Stefania 1-night trip
Posted 17 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Oak Park

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
  • Use the map to find apartments and other holiday homes in the Oak Park neighbourhood you prefer
  • 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 vacation rentals in Oak Park?

Yes, we have vacation rentals in Oak Park close to Oak Park Conservatory, or you can choose a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals are there in Oak Park?

With 30 Expedia vacation rentals, you're sure 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 vacation rental in Oak Park like?

Vacation rentals are private properties you can stay in for several days or longer in Oak Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.