Oak Park Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Oak Park

Dining
Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!

Oak Park
9.8 out of 10, Exceptional, (69)
"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.
The price is ￥16,749
￥45,626 total
includes taxes & fees
Dec 5 - Dec 6
Cozy, Comfortable and Convenient apartment. Close to everything!
Smart TV
Comfy 2-bedroom apartment with AC, WiFi in Oak Park

Comfy 2-bedroom apartment with AC, WiFi in Oak Park

Oak Park
9.2 out of 10, Wonderful, (5)
"Very responsive, parking and nice layout "
United States
Cynthia B.
The price is ￥8,374
￥41,366 total
includes taxes & fees
Dec 8 - Dec 9
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Oak Park
10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ￥31,151
￥85,415 total
includes taxes & fees
Dec 11 - Dec 12
Modern Victorian Vibes ❤️ | Character & Charm
Property grounds
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Oak Park
9.6 out of 10, Exceptional, (96)
"Great central and safe location. Home is quaint and cozy. Some minor updates are needed but it worked well for our visit. Really appreciated the close reserved parking so we always had a spot to park. Host was always in contact and easily accessible if needed."
United States
JoLiz B.
The price is ￥12,898
￥35,095 total
includes taxes & fees
Dec 8 - Dec 9
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Fridge, microwave, oven, stovetop
Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking

Oak Park
9.6 out of 10, Exceptional, (57)
"The home was very clean, had easy parking, and really convenient to downtown Oak Park where there are many restaurants to choose from. The communication from the host was wonderful and we would definitely stay here again. "
United States
Jill J.
The price is ￥12,929
￥34,062 total
includes taxes & fees
Dec 28 - Dec 29
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (12)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is ￥20,664
￥71,805 total
includes taxes & fees
Dec 8 - Dec 9
Vintage Urban Retreat
Fridge, microwave, oven, stovetop
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Oak Park
8.8 out of 10, Excellent, (24)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is ￥11,166
￥32,846 total
includes taxes & fees
Dec 17 - Dec 18
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Interior
Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking

Oak Park
9.8 out of 10, Exceptional, (18)
"Very impressed with the neighborhood and the cleanliness of the unit! Beds were very comfy too! Thank you for hosting our family and looking forward to returning another time!"
United States
Katie S.
The price is ￥24,534
￥56,797 total
includes taxes & fees
Dec 6 - Dec 7
Spacious, lovely 2bed 1bath with free parking
Exterior
Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center

Oak Park
9.8 out of 10, Exceptional, (18)
"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.
The price is ￥34,893
￥105,104 total
includes taxes & fees
Dec 5 - Dec 6
Chic 3bed 2bath Home with free parking close to United Center
Exterior
Oak Park Queen

Oak Park Queen

Oak Park
8.2 out of 10, Very Good, (31)
"Excellent location, very spacious layout.Lots of items to be able to stay comfortably. Very comfortable beds and pillows very clean towels"
United States
Krista W.
The price is ￥15,353
￥36,217 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Oak Park Queen
Fridge, microwave, oven, stovetop
Beautiful, cozy stay in Historic Frank Lloyd Wright District

Beautiful, cozy stay in Historic Frank Lloyd Wright District

Oak Park
9.0 out of 10, Wonderful, (2)
"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.
The price is ￥27,139
￥90,722 total
includes taxes & fees
Dec 28 - Dec 29
Beautiful, cozy stay in Historic Frank Lloyd Wright District
Dining
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

2.0 star property
Oak Park
The price is ￥10,514
￥64,822 total
includes taxes & fees
Dec 8 - Dec 9
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
Interior
Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!

Burr Ridge
9.8 out of 10, Exceptional, (34)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is ￥7,956
￥23,774 total
includes taxes & fees
Dec 5 - Dec 6
Less is more! Pet friendly Tiny Home near Chicago!
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (392)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
The price is ￥26,143
￥34,166 total
includes taxes & fees
Dec 14 - Dec 15
Level Chicago – Old Town
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ￥20,414
￥23,962 total
includes taxes & fees
Dec 7 - Dec 8
Chicago luxury home suites
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is ￥9,615
￥28,273 total
includes taxes & fees
Dec 7 - Dec 8
Twice as Nice: Chic 2BR Stay with Style & Space
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥15,627
￥22,896 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
Interior
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is ￥32,578
￥67,000 total
includes taxes & fees
Dec 11 - Dec 12
Your Chicago get Away
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ￥8,529
￥24,674 total
includes taxes & fees
Dec 7 - Dec 8
Sun-Drenched 1BR Apartment
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Very clean!! Friendly staff, great food!! Enjoyed the historic room! "
Jennifer 1-night trip
Posted 7 hours ago
Congress Plaza Hotel

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:

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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?

LakeHouse: This vacation home rental outside of Oak Park is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Oak Park?

With 28 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.