Oak Park Vacation Rentals

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Our top choices for Oak Park vacation rentals

Vacation Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (33 reviews)
"great stay"
United States
matt R.
$168 nightly
The price is $193
Jan 21 - Jan 22
Total with taxes and fees
A quiet stay while you are away
8.4 out of 10, Very Good, (6 reviews)
"Very responsive, parking and nice layout "
United States
Cynthia B.
$236 nightly
The price is $271
Jan 21 - Jan 22
Total with taxes and fees
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
$349 nightly
The price is $400
Jan 21 - Jan 22
Total with taxes and fees
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
8.8 out of 10, Excellent, (26 reviews)
"Very good communication by the host, well located, clean and comfortable, everything you need!"
Canada
Maxime L.
$176 nightly
The price is $202
Jan 21 - Jan 22
Total with taxes and fees
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
9.8 out of 10, Exceptional, (70 reviews)
"My husband, daughter and I went to Chicago for a weekend getaway and this place was clean, cute and so close to transit. Great place for a small family to stay. "
United States
Amy A.
$257 nightly
The price is $294
Jan 21 - Jan 22
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
9.6 out of 10, Exceptional, (97 reviews)
"The kitchen was fully equipped and the whole apartment was very comfortable. I especially liked the two very clean bathrooms. There were even curling and flat irons for me to do my hair. Wow! So thoughtful!"
United States
Masooma
$230 nightly
The price is $264
Jan 21 - Jan 22
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Apartment in Oak Park

Oak Park Queen
8.2 out of 10, Very Good, (31 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
$194 nightly
The price is $222
Jan 21 - Jan 22
Total with taxes and fees
Oak Park Queen

Vacation Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14 reviews)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$415 nightly
The price is $475
Jan 21 - Jan 22
Total with taxes and fees
Vintage Urban Retreat

Vacation Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (28 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
$443 nightly
The price is $507
Jan 21 - Jan 22
Total with taxes and fees
Oak Park Victorian by FLW Studio
9.8 out of 10, Exceptional, (18 reviews)
"Very nice place and neighborhood."
United States
Charles R.
$319 nightly
The price is $365
Jan 21 - Jan 22
Total with taxes and fees
Spacious, lovely 2bed 1bath with free parking
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
$238 nightly
The price is $272
Jan 26 - Jan 27
Total with taxes and fees
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Vacation Home in Oak Park

New! 10-min to Downtown
2.0 star property
$551 nightly
The price is $590
Jan 21 - Jan 22
Total with taxes and fees
New! 10-min to Downtown
9.0 out of 10, Wonderful, (2 reviews)
"This clean, cozy upper level apartment in a duplex was absolutely perfect for our family trip to visit relatives in Oak Park. The neighborhood setting and off-street parking were really convenient, and it was a comfortable (just less than a mile) walk to the downtown area. We will definitely book here for our next trip. "
United States
Kathryn W.
$488 nightly
The price is $558
Jan 21 - Jan 22
Total with taxes and fees
Beautiful, cozy stay in Historic Frank Lloyd Wright District
2.0 star property
$634 nightly
The price is $679
Jan 21 - Jan 22
Total with taxes and fees
Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
9.8 out of 10, Exceptional, (18 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
$592 nightly
The price is $678
Jan 21 - Jan 22
Total with taxes and fees
Chic 3bed 2bath Home with free parking close to United Center
9.8 out of 10, Exceptional, (37 reviews)
"We loved it! We were in for a short time and it was perfect!!"
United States
nicole l.
$193 nightly
The price is $207
Jan 27 - Jan 28
Total with taxes and fees
Less is more! Pet friendly Tiny Home near Chicago!

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,052 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
$135 nightly
The price is $158
Jan 21 - Jan 22
Total with taxes and fees
Sentral Michigan Avenue

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 21 - Jan 22
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (414 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
$167 nightly
The price is $196
Jan 22 - Jan 23
Total with taxes and fees
Level Chicago – Old Town

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 22 - Jan 23
Total with taxes and fees
West Loop Living – Bright 1BR
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

Find out more about Oak Park

Everything you need to know about Oak Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oak Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This vacation home rental outside of Oak Park offers a patio, a barbecue grill, 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 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 Pleasant Home, 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 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.