Chicago holiday homes
We found 3,704 holiday rentals — enter your dates for availability
Take a look at holiday rentals near Chicago O'Hare International Airport (ORD) that provide the perfect home base for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, such as Wi-Fi and cable TV. Whatever 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, IL (ORD-O'Hare Intl.)
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 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 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$10,368
NZ$10,368
NZ$1,481 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$6,037
NZ$6,037
NZ$862 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 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 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 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$8,191
NZ$8,191
NZ$1,170 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 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 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$7,460
NZ$7,460
NZ$1,066 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,064
NZ$6,064
NZ$866 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$2,613
NZ$2,613
NZ$373 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$10,900
NZ$10,900
NZ$1,557 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 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$8,774
NZ$8,774
NZ$1,253 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 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 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
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(29 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is NZ$3,181
NZ$3,181
NZ$454 per night
includes taxes & fees
Image gallery for Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
8.48.4 out of 10 rating
Very good
(8 reviews)
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
Chicago, IL
7% off
Price is NZ$1,626
NZ$1,626
NZ$232 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
Short Drive from Cernan Earth & Space Center! Kitchen, Free Airport Shuttle!
Sleeps 2 · 1 bedroom · 1 bathroom
8.48.4 out of 10
Very goodvery good
6 reviews(6 reviews)
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Sleeps 4 · 25 bedrooms · 1 bathroom
5.25.2 out of 10
5 reviews(5 reviews)
Chic hotel with WiFi, fitness room, AC in lovely Schaumburg
Sleeps 10 · 1 bedroom · 1 bathroom
The Gem Museum Suites
Sleeps 5 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Offering Spectacular Stay! Full Kitchen, Pet-friendly, Near Cantigny Golf Club!
Sleeps 2 · 1 bedroom · 1 bathroom
7.07.0 out of 10
Goodgood
8 reviews(8 reviews)
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Sleeps 9 · 3 bedrooms · 1 bathroom
5.45.4 out of 10
3 reviews(3 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