Chicago 59th Street Station holiday homes
We found 3,517 holiday rentals — enter your dates for availability
Find the perfect holiday home that's close to Chicago 59th Street Station. Holiday homes provide the best amenities for you and your friends, family or even pets, including parking and a garden. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago 59th Street Station
Showing deals for:17 Oct - 24 Oct
Image gallery for Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
1010 out of 10 rating
Exceptional
(7 reviews)
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
Chicago, IL
7% off
Price is NZ$9,526
NZ$9,526
NZ$1,361 per night
includes taxes & fees
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(14 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
11% off
Price is NZ$7,179
NZ$7,179
NZ$1,026 per night
includes taxes & fees
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$11,222
NZ$11,222
NZ$1,603 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(89 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is NZ$5,423
NZ$5,423
NZ$775 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(31 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is NZ$6,306
NZ$6,306
NZ$901 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(9 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$8,310
NZ$8,310
NZ$1,187 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(28 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,249
NZ$4,249
NZ$607 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is NZ$10,534
NZ$10,534
NZ$1,505 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(40 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,074
NZ$6,074
NZ$868 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is NZ$5,189
NZ$5,189
NZ$741 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
7% off
Price is NZ$7,908
NZ$7,908
NZ$1,130 per night
includes taxes & fees
Image gallery for Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
1010 out of 10 rating
Exceptional
(17 reviews)
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
Chicago, IL
15% off
Price is NZ$6,169
NZ$6,169
NZ$881 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
7% off
Price is NZ$9,506
NZ$9,506
NZ$1,358 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,239
NZ$8,239
NZ$1,177 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$12,099
NZ$12,099
NZ$1,728 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
(5 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is NZ$2,107
NZ$2,107
NZ$301 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(50 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$7,503
NZ$7,503
NZ$1,072 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$11,051
NZ$11,051
NZ$1,579 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
(19 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is NZ$2,875
NZ$2,875
NZ$411 per night
includes taxes & fees
Image gallery for Penthouse Corner 3BR in Streeterville | Roof Deck
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Penthouse Corner 3BR in Streeterville | Roof Deck
Chicago, Illinois
7% off
Price is NZ$9,096
NZ$9,096
NZ$1,299 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$2,626
NZ$2,626
NZ$375 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(31 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,803
NZ$8,803
NZ$1,258 per night
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
7% off
Price is NZ$3,167
NZ$3,167
NZ$452 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(40 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
8% off
Price is NZ$4,092
NZ$4,092
NZ$585 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago 59th Street Station
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
326 reviews(326 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
443 reviews(443 reviews)
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
78 reviews(78 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.48.4 out of 10
Very goodvery good
323 reviews(323 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
822 reviews(822 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
8.08.0 out of 10
Very goodvery good
117 reviews(117 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