Oak Park holiday rentals

We found 2,694 holiday rentals — enter your dates for availability
Discover a selection of 31 homes, 75 apartments and other holiday rentals in Oak Park that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include parking and a hot tub. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oak Park

Showing deals for:20 Nov - 27 Nov

Living area
Terrace/patio
Private kitchen
Interior
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$15,396
for 7 nights, 1 apartment
AU$2,199 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Outdoor dining
Dining
Room
Private kitchen
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,432
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Private kitchen
Interior
Living area
Exterior
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

8% off
AU$9,428
for 7 nights, 1 home
AU$1,347 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Interior
Interior
Interior
Living area
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

8% off
AU$10,378
for 7 nights, 1 home
AU$1,483 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Living area
Living area
Exterior
Interior
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

8% off
AU$10,826
for 7 nights, 1 home
AU$1,547 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Living area
Interior
Interior
Dining
Exceptional
(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

8% off
AU$14,525
for 7 nights, 1 home
AU$2,075 per night
includes taxes & fees
Massive Queen Anne Mansion for your whole family to stay!
Interior
Interior
Living area
Room
Very good
(11 reviews)

Charming Home in Portage Park

Chicago

14% off
AU$1,958
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Charming Home in Portage Park
Interior
Dining
Interior
Private kitchen
Exceptional
(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

8% off
AU$5,834
for 7 nights, 1 home
AU$833 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Bedroom 1 (King Size) + 55Inch TV
Living Room
Front Yard View
Kitchen
Exceptional
(21 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$9,894
for 7 nights, 1 home
AU$1,413 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Room
Interior
Dining
Private kitchen
Exceptional
(39 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,625
for 7 nights, 1 apartment
AU$375 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Room
Interior
Living area
Interior
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$12,471
for 7 nights, 1 home
AU$1,782 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Living room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Living room area opens into dining room & kitchen
Exceptional
(96 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,332
for 7 nights, 1 home
AU$905 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Private kitchen
Living area
Living area
Terrace/patio
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,065
for 7 nights, 1 apartment
AU$581 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
7 minutes drive to downtown and Millenium Park
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Convenient on-premis laundry room with coin operated washer and dryer
Private kitchen
Wonderful
(20 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,691
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Miscellaneous
Living area
Room
Private kitchen
Exceptional
(12 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,861
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Room
Interior
Interior
Private kitchen
Exceptional
(15 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,768
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Living area
Room
Dining
Exceptional
(19 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$2,378
for 7 nights, 1 apartment
AU$340 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Living area
Interior
Room
Dining
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,350
for 7 nights, 1 apartment
AU$336 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Kitchen (upstairs)
Downstairs living area
Upstairs queen bedroom 2
Downstairs living room
Exceptional
(97 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$13,298
for 7 nights, 1 apartment
AU$1,900 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Interior
Private kitchen
Room
Exceptional
(11 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,979
for 7 nights, 1 apartment
AU$426 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior detail
Living area
Room
Private kitchen
Exceptional
(11 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$4,064
for 7 nights, 1 apartment
AU$581 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Living area
Dining
Room
Private kitchen
Wonderful
(18 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$2,373
for 7 nights, 1 apartment
AU$339 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Rooftop lounge leads to roof deck with 360 degree skyline views
Restored grand lobby with work tables, club seating, and stained glass ceiling
Craft cocktail bar in lobby
Heritage Outpost cafe in lobby
Exceptional
(14 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago

7% off
AU$2,964
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Living area
Interior
Private kitchen
Interior
Wonderful
(85 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,832
for 7 nights, 1 apartment
AU$262 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Oak Park getaway

The area's architecture and temples are just some of the reasons to come on holiday to Oak Park. Well known for its restaurants, shopping and local tours, this walkable city won't disappoint. United Center and Wrigley Field are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Oak Park

Are you hoping to find top things to see and do in the city? Venture out of your holiday home and check out everything that makes Oak Park a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Galloping Ghost (6 mi / 9.6 km)
  • Oak Brook Golf Course (8.1 mi / 13 km)
  • Lincoln Park Zoo (8.1 mi / 13.1 km)
  • The Dome at the Parkway Bank Sports Complex (8.1 mi / 13.1 km)
  • Rainbow Falls Waterpark (13.8 mi / 22.3 km)
  • Pirates Cove Childrens Theme Park (14.3 mi / 23.1 km)

Exploring the natural features in Oak Park

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Oak Park is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (8.3 mi / 13.3 km)
  • Grant Park (8.4 mi / 13.6 km)
  • Garfield Park (3.4 mi / 5.5 km)
  • Garfield Park Conservatory (3.4 mi / 5.5 km)
  • Humboldt Park (4.4 mi / 7.1 km)
  • Anna and Frederick Douglass Park (4.6 mi / 7.4 km)

Transport options to and around Oak Park

Fly into Chicago Midway Airport (MDW), the closest airport, located 7 mi (11.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago O'Hare International Airport (ORD), which is 8.9 mi (14.4 km) away.

If you're travelling by train, you can make your way to Oak Park Station. You can get around Oak Park by jumping on the metro at Ridgeland Station (Green Line), Oak Park Station (Green Line) or Oak Park Station (Blue Line).

Frequently asked questions

What is the most popular type of holiday home accommodation in Oak Park?
Apartments are the most popular style of holiday home in Oak Park, according to our data. Even if you have a different vision in mind, Stayz has properties in loads of sizes and shapes. Look through our options to find your perfect match.
How much does it cost to rent a holiday home in Oak Park?
Several things determine what you'll pay for your holiday home in Oak Park, including the type of property, season and length of stay. However, all of our holiday homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Oak Park?
When you travel and the size and style of the property will influence the cost of your beachside holiday home. Put in your Oak Park travel dates to see all your options on Stayz. Can't live without a private pool? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Oak Park?
Yes. There are. You can pick from 52 holiday homes that allow pets in Oak Park. Many of our pet-friendly holiday homes even come with a garden for your fur child to run around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Stayz.
Can I rent a house with a pool in Oak Park?
Add a new level of fun to your getaway by booking one of the four houses with a private pool in Oak Park. Use our handy search filter to find the kind of property you want on Stayz, and then spend your downtime splish-splashing around in a swimming pool that's all your own.
What are popular home amenities in Oak Park?
A garden, a nearby river and a firepit head the list of most popular home amenities in Oak Park. Whether you're planning to travel as a party of one, with your significant other or a bunch of friends, Stayz will help you find a holiday home that suits your tastes with all the features you need.
Are there large group holiday homes in Oak Park?
With two properties that can host 10 guests or more in Oak Park, you won't have to keep anyone off the invite list. From holidays with the extended family to special events like anniversary parties and weddings, Stayz can help you find a large group home to suit the occasion.
Are there holiday homes in Oak Park that welcome kids?
With 51 family-friendly holiday homes available in Oak Park, now is the perfect time to introduce your children to the wonders of travel. Simply click on our "Properties good for families" filter box to search for stays that feature amenities ideal for holidaying families, like multiple bedrooms, patios, bunk beds and hot tubs.
What are the top attractions for families in Oak Park?
Keeping the kids entertained during your Oak Park holiday is a snap with these cool family-friendly attractions:
  • Chicago Riverwalk
  • Shedd Aquarium
  • Field Museum of Natural History
Are there one-bedroom holiday homes in Oak Park?
Yes, you can take your pick from 15 one-bedroom homes in Oak Park. Whether you're on the lookout for a secluded cottage or an upmarket condo, our one-bedroom properties are just right if you don't require loads of space. One of the best parts about having your own pad? You won't need to share your adventure with strangers.
Can I find two-bedroom holiday homes in Oak Park?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 18 two-bedroom holiday homes Oak Park has to offer.
Are there holiday homes with WiFi in Oak Park?
Whether you'd like to keep up with the news, make a video call or surf your social networks, there are 16 holiday homes with WiFi in Oak Park. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Oak Park?
You'll have your pick of 48 holiday homes with air conditioning in Oak Park giving you that gentle, cool breeze and extra element of comfort. Just enter your preferred travel dates and then use our handy filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday home in Oak Park?
The minimum age is usually 16, 18 or 21. It can differ from one property to another on Stayz, so check the rules of your preferred Oak Park stay before booking your trip.
How long can I rent a holiday home in Oak Park for?
The amount of time you can book an Oak Park holiday home for is down to each property. Simply put in your preferred travel dates to view options offering longer term stays. They feature all you require to make your extended trip more comfortable and convenient, like kitchens and yards. Some holiday homes may also offer weekly or monthly discounts, so you can stay longer for less money.

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