Chicago holiday rentals
We found 4,319 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Chicago, IL (CHI-All Airports)
Showing deals for:7 Nov - 14 Nov
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
7% off
Price is S$6,983
S$6,983
S$998 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
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is S$4,202
S$4,202
S$600 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
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is S$4,608
S$4,608
S$658 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, IL
8% off
Price is S$3,977
S$3,977
S$568 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
7% off
Price is S$5,423
S$5,423
S$775 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, IL
7% off
Price is S$5,234
S$5,234
S$748 per night
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is S$6,735
S$6,735
S$962 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
6% off
Price is S$2,512
S$2,512
S$359 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, IL
7% off
Price is S$3,293
S$3,293
S$470 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, IL
7% off
Price is S$5,042
S$5,042
S$720 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is S$2,347
S$2,347
S$335 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
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
14% off
Price is S$2,874
S$2,874
S$411 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
(32 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is S$2,638
S$2,638
S$377 per night
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
7% off
Price is S$4,383
S$4,383
S$626 per night
includes taxes & fees
Image gallery for ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
9.89.8 out of 10 rating
Exceptional
(138 reviews)
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
Oregon, IL
8% off
Price is S$1,987
S$1,987
S$284 per night
includes taxes & fees
Image gallery for The Tailor House
1010 out of 10 rating
Exceptional
(42 reviews)
The Tailor House
Woodstock, IL
14% off
Price is S$2,162
S$2,162
S$309 per night
includes taxes & fees
Image gallery for Spread out - Renovated 5BR+Loft, Sleeps 12+
9.29.2 out of 10 rating
Wonderful
(27 reviews)
Spread out - Renovated 5BR+Loft, Sleeps 12+
Aurora, IL
8% off
Price is S$3,170
S$3,170
S$453 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is S$4,005
S$4,005
S$572 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 S$2,080
S$2,080
S$297 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is S$6,609
S$6,609
S$944 per night
includes taxes & fees
Image gallery for Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
1010 out of 10 rating
Exceptional
(56 reviews)
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Oregon, IL
8% off
Price is S$2,308
S$2,308
S$330 per night
includes taxes & fees
Image gallery for Fox Valley Farmhouse Overlooking The Fox River!
1010 out of 10 rating
Exceptional
(39 reviews)
Fox Valley Farmhouse Overlooking The Fox River!
St. Charles, IL
8% off
Price is S$4,187
S$4,187
S$598 per night
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
14% off
Price is S$5,448
S$5,448
S$778 per night
includes taxes & fees
Image gallery for Lovely 2-Bdrm unit with pool. Home away from home.
8.48.4 out of 10 rating
Very good
(22 reviews)
Lovely 2-Bdrm unit with pool. Home away from home.
Naperville, IL
8% off
Price is S$1,897
S$1,897
S$271 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
Newly updated warm Rockford tri-level house minutes from Bypass 20, I39 and I90!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Relax. Recharge. Reconnect.
Sleeps 7 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
This space close to the Northern Illinois University and I-88 Highway.
Sleeps 5 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
10 reviews(10 reviews)
Shop Chicago and Relax by The Bean | City Viwes | 24-hour Gym | 2 Units
Sleeps 8 · 2 bedrooms · 2 bathrooms
2 Comfortable Units, Complimentary Airport Shuttle, Pets Allowed!
Sleeps 8 · 4 bedrooms · 2 bathrooms
Ideal & Spacious 1BR Apt
Sleeps 2 · 1 bedroom · 1 bathroom
Top rated rentals - Chicago
Great for bonding, cute neighbourhood
1010 out of 10
Exceptionalexceptional
185 reviews(185 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