Chicago South Shore Station holiday rentals
We found 3,415 holiday rentals — enter your dates for availability
If you are looking to stay near Chicago South Shore Station, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the amenities that you expect and more, including parking and a TV. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago South Shore Station
Showing deals for:10 Oct - 17 Oct
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$13,600
AU$13,600
AU$1,943 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 AU$11,076
AU$11,076
AU$1,582 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 AU$14,569
AU$14,569
AU$2,081 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 AU$6,088
AU$6,088
AU$870 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 AU$9,519
AU$9,519
AU$1,360 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
8% off
Price is AU$14,337
AU$14,337
AU$2,048 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 AU$9,490
AU$9,490
AU$1,356 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is AU$6,516
AU$6,516
AU$931 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
8% off
Price is AU$12,665
AU$12,665
AU$1,809 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$3,608
AU$3,608
AU$515 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
8% off
Price is AU$14,112
AU$14,112
AU$2,016 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$12,902
AU$12,902
AU$1,843 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 AU$7,078
AU$7,078
AU$1,011 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$3,441
AU$3,441
AU$492 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 AU$7,078
AU$7,078
AU$1,011 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 AU$7,078
AU$7,078
AU$1,011 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 AU$6,088
AU$6,088
AU$870 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
8% off
Price is AU$14,891
AU$14,891
AU$2,127 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 AU$9,519
AU$9,519
AU$1,360 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 AU$6,088
AU$6,088
AU$870 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 AU$12,223
AU$12,223
AU$1,746 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 AU$6,868
AU$6,868
AU$981 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 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 AU$5,800
AU$5,800
AU$829 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago South Shore Station
Spacious & Comfortable 3 Bedrooms + Bonus Room
Sleeps 10 · 4 bedrooms · 2 bathrooms
Relax in style: Chic 2 bedroom haven in brickell.
Sleeps 4 · 2 bedrooms · 1 bathroom
3.03.0 out of 10
2 reviews(2 reviews)
Essence Suite W/Spa Bath
Sleeps 8 · 2 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
6BR Chicago Gem: Prime, Safe, Family-Friendly Hub
Sleeps 12 · 6 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Sleeps 12 · 5 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
10 reviews(10 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