Orland Park 143rd Street Station holiday rentals
We found 1,094 holiday rentals — enter your dates for availability
If you'd like to stay close to Orland Park 143rd Street Station, scroll through and discover private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. At the end of the day, 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 143rd Street Station
Showing deals for:7 Nov - 14 Nov
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is S$3,446
S$3,446
S$492 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is S$1,615
S$1,615
S$231 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is S$2,337
S$2,337
S$334 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, IL
6% off
Price is S$1,708
S$1,708
S$244 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is S$6,116
S$6,116
S$874 per night
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
11% off
Price is S$5,473
S$5,473
S$782 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is S$3,998
S$3,998
S$571 per night
includes taxes & fees
Image gallery for A quiet stay while you are away
9.89.8 out of 10 rating
Exceptional
(32 reviews)
A quiet stay while you are away
Oak Park, IL
8% off
Price is S$1,356
S$1,356
S$194 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
(16 reviews)
Pool•Outdoor Grill + Bar•Playground•3 king beds•2 Ovens•Fire table
Plainfield, IL
8% off
Price is S$4,446
S$4,446
S$635 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
32% off
Price is S$3,905
S$3,905
S$558 per night
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
14% off
Price is S$5,439
S$5,439
S$777 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.68.6 out of 10 rating
Excellent
(13 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
7% off
Price is S$2,314
S$2,314
S$331 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
7% off
Price is S$1,709
S$1,709
S$244 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is S$1,708
S$1,708
S$244 per night
includes taxes & fees
Image gallery for Spacious home 28 miles from Downtown Chicago
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Spacious home 28 miles from Downtown Chicago
Hammond, IN
8% off
Price is S$2,996
S$2,996
S$428 per night
includes taxes & fees
Image gallery for Home Away From Home
1010 out of 10 rating
Exceptional
(10 reviews)
Home Away From Home
Chicago, IL
11% off
Price is S$3,474
S$3,474
S$496 per night
includes taxes & fees
Image gallery for Zen Oasis of Elegance: Expansive Executive Home
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Zen Oasis of Elegance: Expansive Executive Home
Chicago, IL
8% off
Price is S$6,002
S$6,002
S$857 per night
includes taxes & fees
Image gallery for Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
1010 out of 10 rating
Exceptional
(9 reviews)
Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
Oak Park, IL
8% off
Price is S$9,176
S$9,176
S$1,311 per night
includes taxes & fees
Image gallery for 4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.69.6 out of 10 rating
Exceptional
(9 reviews)
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago, IL
11% off
Price is S$4,513
S$4,513
S$645 per night
includes taxes & fees
Image gallery for Luxury Home Away From Your Home
9.09.0 out of 10 rating
Wonderful
(125 reviews)
Luxury Home Away From Your Home
Chicago, IL
7% off
Price is S$1,940
S$1,940
S$277 per night
includes taxes & fees
Image gallery for Enamored in Elmhurst
1010 out of 10 rating
Exceptional
(11 reviews)
Enamored in Elmhurst
Elmhurst, IL
12% off
Price is S$3,187
S$3,187
S$455 per night
includes taxes & fees
Image gallery for Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
1010 out of 10 rating
Exceptional
(6 reviews)
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Chicago, IL
19% off
Price is S$4,293
S$4,293
S$613 per night
includes taxes & fees
Image gallery for Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
Berwyn, IL
8% off
Price is S$2,010
S$2,010
S$287 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
(11 reviews)
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard, IL
8% off
Price is S$2,530
S$2,530
S$361 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 143rd Street Station
Charming ModernRetro Home!
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
19 reviews(19 reviews)
Long Run Acres Oasis where nature abounds
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
2 Family-Friendly Units Near Downtown Naperville - Free Parking and Breakfast!
Sleeps 8 · 2 bedrooms · 2 bathrooms
Clarendon Hills Garden
Sleeps 2 · 1 bedroom · 0+ bathrooms
7.67.6 out of 10
Goodgood
11 reviews(11 reviews)
Quiet cul-de-sac with huge fenced in backyard
Sleeps 5 · 3 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
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