Chicago holiday rentals
We found 4,317 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Chicago, IL (CHI-All Airports)
Showing deals for:17 Oct - 24 Oct
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 AU$6,579
AU$6,579
AU$940 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 AU$4,950
AU$4,950
AU$707 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 AU$10,034
AU$10,034
AU$1,433 per night
includes taxes & fees
Image gallery for Elegant, charming, serene, & delightful home with huge fenced yard close to I90!
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Elegant, charming, serene, & delightful home with huge fenced yard close to I90!
Loves Park, IL
8% off
Price is AU$3,390
AU$3,390
AU$484 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 AU$7,262
AU$7,262
AU$1,037 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 AU$9,509
AU$9,509
AU$1,358 per night
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, Illinois
8% off
Price is AU$5,567
AU$5,567
AU$795 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 AU$7,222
AU$7,222
AU$1,032 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 AU$5,797
AU$5,797
AU$828 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 AU$7,420
AU$7,420
AU$1,060 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
8% off
Price is AU$8,723
AU$8,723
AU$1,246 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 AU$3,875
AU$3,875
AU$554 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 AU$6,922
AU$6,922
AU$989 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
8.88.8 out of 10 rating
Excellent
(6 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is AU$4,737
AU$4,737
AU$677 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
(28 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is AU$5,425
AU$5,425
AU$775 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$10,918
AU$10,918
AU$1,560 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 AU$7,899
AU$7,899
AU$1,128 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 AU$5,629
AU$5,629
AU$804 per night
includes taxes & fees
Image gallery for Cozy home in Rockford Sleeps 8
8.88.8 out of 10 rating
Excellent
(15 reviews)
Cozy home in Rockford Sleeps 8
Rockford, IL
8% off
Price is AU$1,908
AU$1,908
AU$273 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$2,342
AU$2,342
AU$335 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 AU$2,924
AU$2,924
AU$418 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 AU$2,670
AU$2,670
AU$381 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 AU$3,732
AU$3,732
AU$533 per night
includes taxes & fees
Image gallery for Riverfront cabin on Rock River
1010 out of 10 rating
Exceptional
(187 reviews)
Riverfront cabin on Rock River
Rockford, IL
9% off
Price is AU$1,986
AU$1,986
AU$284 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
Showing deals for: 15 Oct - 18 Oct
Lovely Riverfront House with Fire Pit & 30ft Swing!
Sleeps 6 · 2 bedrooms
9.89.8 out of 10
Exceptionalexceptional
89 reviews(89 reviews)
The current price is AU$1,127
AU$1,127
for 3 nights, 1 home
AU$376 per night
includes taxes & fees
2 Comfortable Units, Complimentary Airport Shuttle, Pets Allowed!
Sleeps 8 · 2 bedrooms · 2 bathrooms
The current price is AU$2,281
AU$2,281
for 3 nights, 1 home
AU$760 per night
includes taxes & fees
Modern 2 King BR Apt, Relax in Style!!
Sleeps 7 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
The current price is AU$1,675
AU$1,675
for 3 nights, 1 apartment
AU$558 per night
includes taxes & fees
Recently renovated home in an inviting neighborhood
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
The current price is AU$1,530
AU$1,530
for 3 nights, 1 home
AU$510 per night
includes taxes & fees
Ideal & Spacious 1BR Apt
Sleeps 2 · 1 bedroom · 1 bathroom
The current price is AU$1,109
AU$1,109
for 3 nights, 1 apartment
AU$370 per night
includes taxes & fees
The Avondale Lower Level
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
The current price is AU$1,505
AU$1,505
for 3 nights, 1 apartment
AU$502 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