Oak Park vacation rentals

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Best Oak Park vacation rentals

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$37 - $450$450 - $862$862 - $1,274$1,274 - $1,686$1,686+ per night

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Most recommended vacation rentals in Oak Park

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Cozy, Comfortable And Convenient Apartment. Close To Everything! - Oak Park
Cozy, Comfortable And Convenient Apartment. Close To Everything!
Oak Park, IL
9.7Wonderful(50)
Free Wi-Fi
$276+
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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)
$175+
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A quiet stay while you are away - Oak Park - Living room
A quiet stay while you are away
Oak Park, IL
9.7Wonderful(27)
Free Wi-Fi
$231+
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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(47)
$194+
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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(34)
Free Wi-Fi
$156+
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The Oak Park Loft - Oak Park - Dining room
The Oak Park Loft
Oak Park, IL
9.6Wonderful(6)
Free Wi-Fi
$286+
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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
$317+
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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
9.0Wonderful(32)
Parking
Free Wi-Fi
$368+
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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
8.6Very good(12)
Parking
Free Wi-Fi
Pet friendly
$220+
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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(16)
Parking
Free Wi-Fi
$288+
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Sunny Jumbo Studio in the Heart of Oak Park - Oak Park - Patio
Sunny Jumbo Studio in the Heart of Oak Park
Oak Park, IL
9.0Wonderful(26)
$184+
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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
$345+
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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
7.7Good(2)
Free Wi-Fi
Pet friendly
$210+
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Peaceful Beauty in Historic District - Walkable - Winter Month Stay Special - Oak Park
Peaceful Beauty in Historic District - Walkable - Winter Month Stay Special
Oak Park, IL
9.7Wonderful(33)
Free Wi-Fi
Pool
$229+
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Charming Chicago-Style, Vintage, Tv Nfl Pass - Oak Park
Charming Chicago-Style, Vintage, Tv Nfl Pass
Oak Park, IL
$138+
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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 $183. The highest prices are found on Saturday, with average rates at $494.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
October
$257
$422
Cheapest month to stay with an average 54% drop in price.
Most expensive month to stay with an average 134% 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 50% 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, 31 reviews), Cozy, Comfortable And Convenient Apartment. Close To Everything! (9.7, 50), and Sunny Coach House in Historic Oak Park (9.7, 47), 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 February.
  • The cheapest night for renting a vacation home in Oak Park is Wednesday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oak Park for 17 days.

FAQs when booking a vacation home in Oak Park

  • How much is a vacation rental for a week in Oak Park?

    The average price for a weekly Oak Park vacation rental found by KAYAK users in the last 2 weeks is $1,133.

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

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

  • What types of vacation rentals are available in Oak Park?

    There are loads of different property types that you can make your vacation home in Oak Park. You’ll find apartments, bungalows, condos, houses and homestays.

  • Are there any pet-friendly vacation rentals in Oak Park?

    There are a number of dog and pet-friendly Oak Park vacation rentals, with around 13% allowing you to bring your pet along with you.

  • How much is a vacation rental in Oak Park for tonight?

    In the last 72 hours, users have found Oak Park vacation rentals for tonight for as low as $196. Search here for similar prices

  • How much is a vacation rental in Oak Park for this weekend?

    In the last 72 hours, users have found Oak Park vacation rentals for this weekend for as low as $234 per night. Search here for similar prices

  • How can I find vacation rentals near me in Oak Park?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

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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