Chicago 87th Street Station holiday homes
We found 3,356 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Chicago 87th Street Station (South Chicago). Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and air conditioning. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Chicago 87th Street Station (South Chicago)
Showing deals for:10 Oct - 17 Oct
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(13 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$14,117
NZ$14,117
NZ$2,017 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,634
NZ$11,634
NZ$1,662 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is NZ$15,171
NZ$15,171
NZ$2,167 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,755
NZ$6,755
NZ$965 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$16,573
NZ$16,573
NZ$2,368 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$10,307
NZ$10,307
NZ$1,472 per night
includes taxes & fees
Image gallery for #1402 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(25 reviews)
#1402 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$10,434
NZ$10,434
NZ$1,491 per night
includes taxes & fees
Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury SOHO Styled Two-Level Townhouse - Old Town
Chicago, Illinois
7% off
Price is NZ$13,152
NZ$13,152
NZ$1,879 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 NZ$3,918
NZ$3,918
NZ$560 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(20 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
7% off
Price is NZ$14,714
NZ$14,714
NZ$2,102 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$8,016
NZ$8,016
NZ$1,145 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$12,488
NZ$12,488
NZ$1,784 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(17 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$8,016
NZ$8,016
NZ$1,145 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$8,016
NZ$8,016
NZ$1,145 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,755
NZ$6,755
NZ$965 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 NZ$3,748
NZ$3,748
NZ$535 per night
includes taxes & fees
Image gallery for #1501 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(7 reviews)
#1501 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$10,434
NZ$10,434
NZ$1,491 per night
includes taxes & fees
Image gallery for Kasa | Classic 2 BD + Near Grant Park | Chicago
1010 out of 10 rating
Exceptional
(6 reviews)
Kasa | Classic 2 BD + Near Grant Park | Chicago
Chicago, Illinois
8% off
Price is NZ$13,755
NZ$13,755
NZ$1,965 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
7% off
Price is NZ$17,058
NZ$17,058
NZ$2,437 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,755
NZ$6,755
NZ$965 per night
includes taxes & fees
Image gallery for Hike to the beach or stay in all day!
8.68.6 out of 10 rating
Excellent
(11 reviews)
Hike to the beach or stay in all day!
Gary, IN
8% off
Price is NZ$7,683
NZ$7,683
NZ$1,098 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 NZ$5,200
NZ$5,200
NZ$743 per night
includes taxes & fees
Image gallery for Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
Chicago, IL
11% off
Price is NZ$6,448
NZ$6,448
NZ$921 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 NZ$7,960
NZ$7,960
NZ$1,137 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago 87th Street Station
Miller Beach Getaway!
Sleeps 14 · 4 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Charming 3-bed, 3-bath house in amazing Chicago, 10 min from Midway Airport.
Sleeps 4 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
296 reviews(296 reviews)
Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
LakeHouse
Sleeps 16 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
19 reviews(19 reviews)
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
Sleeps 6 · 3 bedrooms · 2 bathrooms
6.86.8 out of 10
6 reviews(6 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