A well-maintained garden with a lawn, a large tree, and a two-story house with a porch.

Oak Park Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Oak Park vacation rentals

Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ￥39,144
￥62,857 total
includes taxes & fees
Jul 26 - Jul 27
At Home in Oak Park
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ￥34,871
￥57,967 total
includes taxes & fees
Aug 17 - Aug 18
Historic Oak Park Home
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥29,528
￥51,850 total
includes taxes & fees
Aug 3 - Aug 4
The Oak Park Loft
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is ￥45,036
￥69,603 total
includes taxes & fees
Jul 27 - Jul 28
Historic Oak Park Residence
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,219 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is ￥24,571
￥33,613 total
includes taxes & fees
Aug 17 - Aug 18
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (504 reviews)
"Perfect location"
United States
Diana
The price is ￥46,041
￥58,052 total
includes taxes & fees
Aug 17 - Aug 18
Level Chicago – Old Town
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.6 out of 10, Exceptional, (166 reviews)
"Beautiful hotel, gardened a plus! Located in very nice neighborhood, near the train, breakfast was vey good well. Would stay there again"
United States
Jacob
The price is ￥23,986
￥27,460 total
includes taxes & fees
Aug 20 - Aug 21
The Gem Museum Suites
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.8 out of 10, Excellent, (43 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ￥33,774
￥39,649 total
includes taxes & fees
Jul 22 - Jul 23
Wrigleyville Suites
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Only issue is getting there so you are able to pay the guest parking fee and it would be nice if it is overnight that you only pay once and.not if you leave and come back several times. It becomes very costly as a public parking ticket holder."
Laura 1-night trip
Posted less than an hour ago
Crowne Plaza Chicago West Loop by IHG

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 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.

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

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Oak Park is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oak Park?

With 33 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 Pleasant Home, 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 United Center and Wrigley Field.

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.