Apartment holiday rentals in Oak Park
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Top-rated apartment rentals in Oak Park
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Park apartment rentals
Weekly apartment rentals
Flat in Oak Park
4.91 out of 5 average rating, 171 reviewsLarge sunny 3BR apt. in downtown Oak Park
14–21 Nov
Flat in Forest Park
4.9 out of 5 average rating, 124 reviewsLarge Renovated 1st FL Suite Forest Park/Oak Park
1–8 Oct
Flat in Forest Park
4.9 out of 5 average rating, 101 reviewsThe Belvidere
17–24 Jan
Flat in Berwyn
4.99 out of 5 average rating, 253 reviewsBerwyn Betty Apartment
3–10 Feb
Flat in Oak Park
4.94 out of 5 average rating, 157 reviewsA quiet stay while you are away
31 Dec – 7 Jan
Flat in Oak Park
4.79 out of 5 average rating, 169 reviewsCozy modern unit w/ easy access to downtown Chi
14–21 Jul
Flat in Berwyn
4.87 out of 5 average rating, 137 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
11–18 Jul
Flat in Chicago
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
14–21 Oct
Private apartment rentals
Flat in Oak Park
4.94 out of 5 average rating, 105 reviewsEclectic Beauty *Walk to Everything*
25 Sep – 2 Oct
Flat in Chicago
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
20–27 Feb
Flat in Oak Park
4.87 out of 5 average rating, 149 reviewsSmall But Mighty 700 Sqft Cottage Apt (1BR/1BA)
Flat in Chicago
4.95 out of 5 average rating, 170 reviewsFlexible Apt. for 8 by Oak Park-CHI
8–15 Oct
Flat in Berwyn
4.94 out of 5 average rating, 126 reviewsSpacious Oasis Berwyn with Free Parking
24 Nov – 1 Dec
Flat in Chicago
4.99 out of 5 average rating, 181 reviewsNW Chicago Apartment in Safe Neighborhood
8–15 Sep
Flat in Chicago
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
7–14 Jul
Flat in Forest Park
4.99 out of 5 average rating, 89 reviewsSunny 1 bedroom apartment 1 block from restaurants
24–31 Jan
Apartment rentals with a hot tub
Flat in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
2–9 Oct
Flat in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
9–16 Oct
Flat in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
20–27 Apr
Flat in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
20–27 Nov
Flat in Chicago
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
15–22 Mar
Flat in Chicago
5.0 out of 5 average rating, 17 reviewsSpacious Beautiful Condo
16–23 Oct
Flat in Chicago
4.8 out of 5 average rating, 10 reviewsSpacious & Homey Chicago 2BR Apartment
7–14 Jun
Flat in Chicago
5.0 out of 5 average rating, 25 reviewsBelmont Pleasures - hot tub / arcade gaming room
11–18 Dec
Quick stats about flat rentals in Oak Park
Total rentals
130 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
7.5K reviews
Nightly prices starting at
$14 SGD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
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