Chicago 27th Street Station holiday homes
We found 3,581 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals within easy reach of Chicago 27th Street Station that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, including parking and a TV. No matter what you're looking for, 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 - Chicago 27th 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$9,538
NZ$9,538
NZ$1,363 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$7,145
NZ$7,145
NZ$1,021 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$5,390
NZ$5,390
NZ$770 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$11,226
NZ$11,226
NZ$1,604 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$6,268
NZ$6,268
NZ$895 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$8,592
NZ$8,592
NZ$1,227 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$4,224
NZ$4,224
NZ$603 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$4,783
NZ$4,783
NZ$683 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$10,415
NZ$10,415
NZ$1,488 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$6,149
NZ$6,149
NZ$878 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
(16 reviews)
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
Chicago, IL
15% off
Price is NZ$6,132
NZ$6,132
NZ$876 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
8% off
Price is NZ$7,399
NZ$7,399
NZ$1,057 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$2,712
NZ$2,712
NZ$387 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$9,556
NZ$9,556
NZ$1,365 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$8,052
NZ$8,052
NZ$1,150 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$2,094
NZ$2,094
NZ$299 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$2,805
NZ$2,805
NZ$401 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$10,900
NZ$10,900
NZ$1,557 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$2,571
NZ$2,571
NZ$367 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$7,339
NZ$7,339
NZ$1,048 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 NZ$11,826
NZ$11,826
NZ$1,689 per night
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(15 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
7% off
Price is NZ$3,150
NZ$3,150
NZ$450 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$8,657
NZ$8,657
NZ$1,237 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$4,068
NZ$4,068
NZ$581 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Chicago 27th Street Station
Showing deals for: 11 Oct - 14 Oct
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
325 reviews(325 reviews)
The current price is NZ$5,502
NZ$5,502
for 3 nights, 1 room
NZ$1,834 per night
includes taxes & fees
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
441 reviews(441 reviews)
The current price is NZ$3,261
NZ$3,261
for 3 nights, 1 room
NZ$1,087 per night
includes taxes & fees
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
818 reviews(818 reviews)
The current price is NZ$4,273
NZ$4,273
for 3 nights, 1 room
NZ$1,424 per night
includes taxes & fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
563 reviews(563 reviews)
The current price is NZ$2,399
NZ$2,399
for 3 nights, 1 room
NZ$800 per night
includes taxes & fees
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
The current price is NZ$3,008
NZ$3,008
for 3 nights, 1 room
NZ$1,003 per night
includes taxes & fees
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
318 reviews(318 reviews)
The current price is NZ$4,896
NZ$4,896
for 3 nights, 1 room
NZ$1,632 per night
includes taxes & fees
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