Oak Park vacation rentals

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Best Oak Park vacation rentals

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$37 - $1,127$1,127 - $2,216$2,216 - $3,306$3,306 - $4,395$4,395+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Oak Park

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Cozy, Comfortable And Convenient Apartment. Close To Everything! - Oak Park - Living room
Cozy, Comfortable And Convenient Apartment. Close To Everything!
Oak Park, IL
9.7Wonderful(52)
Free Wi-Fi
$251+
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1br Apartment - Walk To Shops - Downtown Oak Park - Oak Park - Kitchen
1br Apartment - Walk To Shops - Downtown Oak Park
Oak Park, IL
8.6Very good(28)
$165+
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Chic Suite/Mins to L Train /Laundry/Free Parking - Oak Park - Living room
Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park, IL
9.5Wonderful(37)
Free Wi-Fi
$150+
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Sunny Coach House in Historic Oak Park - Oak Park - Living room
Sunny Coach House in Historic Oak Park
Oak Park, IL
9.7Wonderful(48)
$192+
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The Oak Park Loft - Oak Park - Dining room
The Oak Park Loft
Oak Park, IL
9.7Wonderful(6)
Free Wi-Fi
$256+
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A quiet stay while you are away - Oak Park - Pool
A quiet stay while you are away
Oak Park, IL
9.7Wonderful(27)
Free Wi-Fi
$203+
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Lovely vintage Oak Park 3bd 1ba perfectly located near public transit & Chicago - Oak Park - Dining room
Lovely vintage Oak Park 3bd 1ba perfectly located near public transit & Chicago
Oak Park, IL
9.0Wonderful(18)
Parking
Free Wi-Fi
$298+
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Oak Park, IL, entire house, short walk to train. - Oak Park - Living room
Oak Park, IL, entire house, short walk to train.
Oak Park, IL
9.3Wonderful(17)
Free Wi-Fi
$262+
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Gallery Loft of Oak Park #1 Top Host in IL - Oak Park - Dining room
Gallery Loft of Oak Park #1 Top Host in IL
Oak Park, IL
8.8Very good(15)
Parking
Free Wi-Fi
Pet friendly
$189+
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Historic Oak Park Home for 6 / Hemingway District - Oak Park - Bedroom
Historic Oak Park Home for 6 / Hemingway District
Oak Park, IL
8.9Very good(33)
Parking
Free Wi-Fi
$293+
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Insta-Worthy Loft+condo, Free Parking, Near Downtown Chicago - Oak Park - Living room
Insta-Worthy Loft+condo, Free Parking, Near Downtown Chicago
Oak Park, IL
10Wonderful(3)
Free Wi-Fi
$316+
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Comfy 2-bedroom apartment with AC, WiFi in Oak Park - Oak Park
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
Oak Park, IL
10Wonderful(1)
$272+
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Cozy 3 Bdrm. Apt. sleeps 5 guests in the historic neighborhood of Oak Park IL - Oak Park - Living room
Cozy 3 Bdrm. Apt. sleeps 5 guests in the historic neighborhood of Oak Park IL
Oak Park, IL
7.3Good(3)
Free Wi-Fi
$366+
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Oak Park Il · Charming Retro 2br Cottage/Train/Laundry/Free Pkg - Oak Park - Living room
Oak Park Il · Charming Retro 2br Cottage/Train/Laundry/Free Pkg
Oak Park, IL
9.4Wonderful(7)
$208+
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Homestay - Homestay - Oak Park Arts District Homestay - Oak Park
Homestay - Homestay - Oak Park Arts District Homestay
Oak Park, IL
$76+
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8 Mi to Chicago Oak Park Home with Fenced Backyard! - Oak Park
8 Mi to Chicago Oak Park Home with Fenced Backyard!
Oak Park, IL
8.2Very good(2)
Free Wi-Fi
Pet friendly
$206+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Oak Park

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Oak Park with confidence.

What is the cheapest day of the week to book a vacation rental in Oak Park?

Wednesday offers the lowest rates in Oak Park, with an average nightly price of $178. The highest prices are found on Friday, with average rates at $379.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
October
$249
$339
Cheapest month to stay with an average 50% drop in price.
Most expensive month to stay with an average 33% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Oak Park vacation rental deals

  • Vacation rentals in Oak Park are around 87% more expensive than hotels on average. Search here to compare prices for all accommodation types in Oak Park.
  • The best vacation rental properties in Oak Park are Relaxing Oak Park Home (9.8, 33 reviews), Cozy, Comfortable And Convenient Apartment. Close To Everything! (9.7, 52), and Sunny Coach House in Historic Oak Park (9.7, 48), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Oak Park, you should consider visiting during the low season. The cheapest vacation homes in Oak Park can be found in April and March.
  • The cheapest night for renting a vacation home in Oak Park is Wednesday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oak Park for 18 days.

FAQs when booking a vacation home in Oak Park

  • How much is a Rental rental for a month in Oak Park?

    The average price for a monthly Oak Park Rental rental found by KAYAK users in the last 2 weeks is $4,854.

Where to stay in Oak Park?

Our map will help you find the perfect place to stay in Oak Park by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Oak Park

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