Oak Park Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Oak Park

Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, 18 reviews
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 445 reviews
"Great location and the view was fabulous! We had a very comfortable stay. Communication was excellent."
The price is AU$346
per night
1 July - 2 July
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, 98 reviews
"The property was very clean and I loved the fact that it had a kitchen for you to cook. What I did not like was that there was no market close enough to buy groceries. I also didn't like the fact that the TV was not accesible for us, even though, I payed the late fees for a late check out. "
The price is AU$189
per night
8 July - 9 July
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 318 reviews
"Comfortable to stay"
The price is AU$283
per night
2 July - 3 July
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 259 reviews
"The location is great and the room is fully equipped with the useful home appliances like dish washer, laundry and dryer. It’s very helpful for the long stay travelers."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 218 reviews
"Great location, great staff"
The price is AU$462
per night
30 June - 1 July
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 135 reviews
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is AU$208
per night
14 July - 15 July
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 80 reviews
"I like the hotel, I did not realize there was no cleaning services or fresh towels. After 4 days the room needed some freshing and clean wash rags and towels. There was a washing machine but doing laundry on vacation is not for me."
The price is AU$380
per night
30 June - 1 July
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, 36 reviews
"Property was in a safe, walkable area with plenty of food options. It also wasn't far from downtown Chicago/Michigan Ave. The rooms were nice and clean."
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 191 reviews
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is AU$144
per night
19 June - 20 June
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 69 reviews
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
The price is AU$310
per night
30 June - 1 July
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, 111 reviews
"Loved it "
The price is AU$356
per night
7 July - 8 July
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 166 reviews
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is AU$250
per night
15 July - 16 July
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, 107 reviews
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 11 reviews
"Thank you especially to the front desk clerk, he was very friendly and helpful. Place was clean and nice"
The price is AU$356
per night
30 June - 1 July
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
10.0 out of 10, Exceptional, 41 reviews
"As advertised , great location and clean apartment with the basic necessities. Could be a little more clear about which entrance to use during check in as not all of us are familiar with a “garden” entrance. Would stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
LakeHouse
10.0 out of 10, Exceptional, 7 reviews
"Great"
LakeHouse
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, 200 reviews
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Don't see what you're looking for?
See all available properties in Oak Park
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.

Oak Park Holiday Home Travel Info

Number of holiday homes
9
Popular accommodation
Oak Park apartments
Known landmarks
Art Institute of Chicago, Chicago Riverwalk and Chicago Theatre
International airports
Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

Other types of properties in Oak Park you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 7,025 reviews
"Great values. "
The price is AU$241
per night
1 July - 2 July
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, 2,404 reviews
"Alma was our checkin agent and she was amazing! So kind!! Do miss the extra sink in bedroom and would love another chair for seating Otherwise great"
The price is AU$323
per night
1 July - 2 July
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,967 reviews
"I had a wonderful time "
The price is AU$288
per night
1 July - 2 July
River Hotel
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.

Everything you need to know about Oak Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oak Park holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Park holiday rentals we have selected for you start as low as AU$144 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park holiday 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 holiday.

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 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.

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

Your Home Away From Home: This holiday home rental outside of Oak Park offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

How many holiday rentals are there in Oak Park?

With 23 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 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 Grant Park.

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.

Recent reviews of Oak Park properties
Expedia verified reviews