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Oak Park Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Oak Park holiday rentals

A building with a white exterior and a tree with white blossoms in front.

1. 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 HK$1,502
HK$2,591 total
includes taxes & fees
13 Sept - 14 Sept
Historic Oak Park Residence
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

2. 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 HK$1,585
HK$2,685 total
includes taxes & fees
16 Sept - 17 Sept
The Oak Park Loft
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,283 reviews)
"Nice stay"
United States
Heather
The price is HK$1,185
HK$1,621 total
includes taxes & fees
8 Sept - 9 Sept
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$1,859
HK$2,376 total
includes taxes & fees
31 Aug - 1 Sept
Level Chicago – Old Town

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (19 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,442
HK$2,180 total
includes taxes & fees
3 Sept - 4 Sept
Kasa Lake Shore Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

6. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (224 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
The price is HK$1,270
HK$1,453 total
includes taxes & fees
30 Aug - 31 Aug
The Gem Museum Suites
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

7. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is HK$1,677
HK$3,486 total
includes taxes & fees
8 Sept - 9 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

8. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very good, (52 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,312
HK$1,540 total
includes taxes & fees
26 Aug - 27 Aug
Wrigleyville Suites
A red brick building with a blue awning and a sign reading "747 LOFTS."

9. Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is HK$1,505
HK$3,040 total
includes taxes & fees
30 Aug - 31 Aug
Chicago Third Floor Studio by 747 Lofts
A modern interior with a large metallic chair, a glass table, and a black sofa.

10. Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
The price is HK$674
HK$1,280 total
includes taxes & fees
2 Sept - 3 Sept
Cabin 105 by 747 Lofts
A compact kitchen with a stainless steel refrigerator, wooden cabinets, a black leather sofa, and a small table.

11. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (19 reviews)
"Loved the space and location "
United States
Caroline
The price is HK$1,450
HK$2,237 total
includes taxes & fees
27 Aug - 28 Aug
River West, Third Floor Chicago by 747 Lofts
A compact living space with a kitchenette, a sofa, a bed, and a television mounted on the wall.

12. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is HK$706
HK$1,319 total
includes taxes & fees
9 Sept - 10 Sept
Ground Floor Studios in Chicago by 747 Lofts
A modern kitchen with wooden cabinets, a microwave, and a stove. There is a purple sofa and a small table with chairs. A suitcase is on the floor next to the sofa.

13. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is HK$1,302
HK$2,054 total
includes taxes & fees
10 Sept - 11 Sept
Chicago Second Floor Studio by 747 Lofts
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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Clean and great location."
Faiq 1-night trip
Posted less than an hour ago
The Allegro Royal Sonesta Hotel Chicago Loop

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
  • Use the map to find apartments and other holiday homes in the Oak Park neighbourhood you prefer
  • 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 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Oak Park is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Oak Park?

With 30 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 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 Soldier Field.

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.