Chicago 87th Street Station vacation rentals
We found 3,423 vacation rentals — enter your dates for availability
Choose the right vacation rental within close proximity to Chicago 87th Street Station (South Chicago). Vacation homes provide the amenities you need and want for your family, friends, or furry companion, like WiFi and parking. At the end of the day, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Chicago 87th Street Station (South Chicago)
Showing deals for:Nov 7 - Nov 14
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $449
CA $449
CA $4,491 total
CA $4,491 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $528
CA $528
CA $5,326 total
CA $5,326 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
10% off
Price is CA $759
CA $759
CA $7,480 total
CA $7,480 total
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
28% off
Price is CA $2,967
CA $2,967
CA $27,981 total
CA $27,981 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
10% off
Price is CA $503
CA $503
CA $4,945 total
CA $4,945 total
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, IL
10% off
Price is CA $440
CA $440
CA $4,145 total
CA $4,145 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.89.8 out of 10 rating
Exceptional
(12 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $553
CA $553
CA $5,612 total
CA $5,612 total
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
10% off
Price is CA $575
CA $575
CA $5,812 total
CA $5,812 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $574
CA $574
CA $5,671 total
CA $5,671 total
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $731
CA $731
CA $7,224 total
CA $7,224 total
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
10% off
Price is CA $197
CA $197
CA $1,721 total
CA $1,721 total
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
10% off
Price is CA $439
CA $439
CA $4,337 total
CA $4,337 total
includes taxes & fees
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $398
CA $398
CA $4,353 total
CA $4,353 total
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
19% off
Price is CA $300
CA $300
CA $3,061 total
CA $3,061 total
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, IL
10% off
Price is CA $542
CA $542
CA $5,452 total
CA $5,452 total
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
10% off
Price is CA $464
CA $464
CA $4,686 total
CA $4,686 total
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(33 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
10% off
Price is CA $278
CA $278
CA $2,813 total
CA $2,813 total
includes taxes & fees
Image gallery for Miller Beach Getaway!
9.49.4 out of 10 rating
Exceptional
(72 reviews)
Miller Beach Getaway!
Gary, IN
10% off
Price is CA $328
CA $328
CA $3,775 total
CA $3,775 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $813
CA $813
CA $7,526 total
CA $7,526 total
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
10% off
Price is CA $208
CA $208
CA $2,178 total
CA $2,178 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(185 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $475
CA $475
CA $4,874 total
CA $4,874 total
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
10% off
Price is CA $174
CA $174
CA $1,821 total
CA $1,821 total
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
10% off
Price is CA $433
CA $433
CA $4,281 total
CA $4,281 total
includes taxes & fees
Image gallery for Charming Miller Beach Cottage
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Charming Miller Beach Cottage
Gary, IN
10% off
Price is CA $241
CA $241
CA $2,405 total
CA $2,405 total
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
72 reviews(72 reviews)
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Sleeps 18 · 8 bedrooms · 3 bathrooms
LakeHouse
Sleeps 16 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
20 reviews(20 reviews)
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Sleeps 24 · 6 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
60 reviews(60 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
301 reviews(301 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Sleeps 8 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Top rated rentals - Chicago 87th Street Station
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
Spent 4 nights, we had everything we needed, plus nice extra touches. Location is central and close to some great neighborhoods. Jessica was very responsive and even accommodated an early check-in for a bit extra. Would definitely stay here again.
Alex P.
Stayed May 2024
Friend trip to Chicago
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
We were a group of 8 40+ yr old females. We all found the house very very clean and comfortable. We spent most of our time downtown so didn’t get a chance to explore the neighborhood too much, though we felt very safe at all times.
I would recommend this property to all.
Sarah M.
Stayed Oct 2023
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
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, yards and more
More for lessMore space, more privacy, more amenities — more value