Orland Park 153rd Street Station holiday rentals
We found 689 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's near Orland Park 153rd Street Station. Holiday homes offer the best amenities for your family, friends or furry companion, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Orland Park 153rd Street Station
Showing deals for:3 Oct - 10 Oct
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(27 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is AU$3,858
AU$3,858
AU$551 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is AU$2,739
AU$2,739
AU$391 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
1010 out of 10 rating
Exceptional
(18 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is AU$2,528
AU$2,528
AU$361 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, Illinois
7% off
Price is AU$2,568
AU$2,568
AU$367 per night
includes taxes & fees
Image gallery for The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Chicago, IL
16% off
Price is AU$4,746
AU$4,746
AU$678 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
33% off
Price is AU$5,681
AU$5,681
AU$812 per night
includes taxes & fees
Image gallery for Pool_Outdoor Grill + Bar_Playground_3 king beds_2 Ovens_Fire table
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Pool_Outdoor Grill + Bar_Playground_3 king beds_2 Ovens_Fire table
Plainfield, IL
8% off
Price is AU$5,656
AU$5,656
AU$808 per night
includes taxes & fees
Image gallery for PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
9.69.6 out of 10 rating
Exceptional
(10 reviews)
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard, IL
8% off
Price is AU$3,188
AU$3,188
AU$455 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.48.4 out of 10 rating
Very good
(11 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
7% off
Price is AU$2,746
AU$2,746
AU$392 per night
includes taxes & fees
Image gallery for Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
Berwyn, IL
8% off
Price is AU$2,585
AU$2,585
AU$369 per night
includes taxes & fees
Image gallery for Oak Park, IL, entire house, short walk to train.
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Oak Park, IL, entire house, short walk to train.
Oak Park, IL
8% off
Price is AU$3,398
AU$3,398
AU$485 per night
includes taxes & fees
Image gallery for Entire 3bd home Comfortable Private
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Entire 3bd home Comfortable Private
Markham, IL
6% off
Price is AU$2,339
AU$2,339
AU$334 per night
includes taxes & fees
Image gallery for Modern apartment in great central location!
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Modern apartment in great central location!
Forest Park, IL
17% off
Price is AU$2,381
AU$2,381
AU$340 per night
includes taxes & fees
Image gallery for Finished Basement in Historic Oak Park with 2 cats
8.48.4 out of 10 rating
Very good
(5 reviews)
Finished Basement in Historic Oak Park with 2 cats
Oak Park, IL
9% off
Price is AU$1,285
AU$1,285
AU$184 per night
includes taxes & fees
Image gallery for PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.89.8 out of 10 rating
Exceptional
(15 reviews)
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle, IL
8% off
Price is AU$2,883
AU$2,883
AU$412 per night
includes taxes & fees
Image gallery for MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!
1010 out of 10 rating
Exceptional
(10 reviews)
MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!
Chicago, IL
7% off
Price is AU$4,210
AU$4,210
AU$601 per night
includes taxes & fees
Image gallery for Cozy 3-bedroom vacation home just 17 minutes from Lake Michigan
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Cozy 3-bedroom vacation home just 17 minutes from Lake Michigan
Calumet Park, IL
7% off
Price is AU$1,824
AU$1,824
AU$261 per night
includes taxes & fees
Image gallery for Marvel - 4BR’s, 2 BA & Game Room
8.48.4 out of 10 rating
Very good
(8 reviews)
Marvel - 4BR’s, 2 BA & Game Room
Mokena, IL
17% off
Price is AU$4,578
AU$4,578
AU$654 per night
includes taxes & fees
Image gallery for Spacious two bedroom condo with a cozy feel!
8.48.4 out of 10 rating
Very good
(5 reviews)
Spacious two bedroom condo with a cozy feel!
Chicago, IL
7% off
Price is AU$2,501
AU$2,501
AU$357 per night
includes taxes & fees
Image gallery for Suburban Haven: Cozy Escape with a Touch of Luxury
1010 out of 10 rating
Exceptional
(6 reviews)
Suburban Haven: Cozy Escape with a Touch of Luxury
Homewood, IL
6% off
Price is AU$6,704
AU$6,704
AU$958 per night
includes taxes & fees
Image gallery for Cozy 2- bedroom w/ patio mins from Midway Airport
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Cozy 2- bedroom w/ patio mins from Midway Airport
Chicago, IL
11% off
Price is AU$1,798
AU$1,798
AU$257 per night
includes taxes & fees
Image gallery for Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
Chicago, IL
8% off
Price is AU$3,239
AU$3,239
AU$463 per night
includes taxes & fees
Image gallery for Modern "Blast From The Past" A Real Retreat 3Bedroom Unit
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern "Blast From The Past" A Real Retreat 3Bedroom Unit
Chicago, IL
7% off
Price is AU$2,431
AU$2,431
AU$347 per night
includes taxes & fees
Image gallery for King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House
1010 out of 10 rating
Exceptional
(35 reviews)
King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House
Joliet, IL
6% off
Price is AU$3,193
AU$3,193
AU$456 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Orland Park 153rd Street Station
1-bedroom condo next to Chicago Midway International Airport
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Clarendon Hills Garden
Sleeps 2 · 1 bedroom · 0+ bathrooms
8.48.4 out of 10
Very goodvery good
8 reviews(8 reviews)
Charming Updated guest house in Lovely Quiet Neighborhood
Sleeps 4 · 1 bedroom · 1+ bathroom
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value