Chicago holiday homes
We found 3,949 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Chicago, IL (CHI-All Airports)
Showing deals for:8 Aug - 15 Aug
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$12,470
NZ$12,470
NZ$1,781 per night
includes taxes & fees
Image gallery for Chic 2BR 2BA Condo with Balcony - River North Chicago
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Chic 2BR 2BA Condo with Balcony - River North Chicago
Chicago, Illinois
8% off
Price is NZ$10,172
NZ$10,172
NZ$1,453 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,481
NZ$3,481
NZ$497 per night
includes taxes & fees
Image gallery for Balance Work, Play & Rest @WestLoop |TheFlame
1010 out of 10 rating
Exceptional
(31 reviews)
Balance Work, Play & Rest @WestLoop |TheFlame
Chicago, Illinois
8% off
Price is NZ$9,489
NZ$9,489
NZ$1,356 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$8,987
NZ$8,987
NZ$1,284 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
8% off
Price is NZ$9,434
NZ$9,434
NZ$1,348 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(226 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,693
NZ$6,693
NZ$956 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,295
NZ$6,295
NZ$899 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,335
NZ$8,335
NZ$1,191 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(14 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is NZ$13,673
NZ$13,673
NZ$1,953 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,644
NZ$4,644
NZ$663 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,481
NZ$3,481
NZ$497 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
(46 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,046
NZ$6,046
NZ$864 per night
includes taxes & fees
Image gallery for Stylish Corner 2BR in the Loop | City & Lake Views
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Stylish Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,092
NZ$6,092
NZ$870 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,586
NZ$6,586
NZ$941 per night
includes taxes & fees
Image gallery for SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
9.89.8 out of 10 rating
Exceptional
(80 reviews)
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Chicago, IL
8% off
Price is NZ$6,087
NZ$6,087
NZ$870 per night
includes taxes & fees
Image gallery for Unbelievable!Gold Coast’s Finest Stay|The Athena
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Unbelievable!Gold Coast’s Finest Stay|The Athena
Chicago, IL
8% off
Price is NZ$8,979
NZ$8,979
NZ$1,283 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
(13 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
11% off
Price is NZ$10,084
NZ$10,084
NZ$1,441 per night
includes taxes & fees
Image gallery for Gorgeous, Newly Built Guesthouse In Charming Downtown Geneva!
1010 out of 10 rating
Exceptional
(9 reviews)
Gorgeous, Newly Built Guesthouse In Charming Downtown Geneva!
Geneva, IL
8% off
Price is NZ$3,262
NZ$3,262
NZ$466 per night
includes taxes & fees
Image gallery for King Bed - Entire Home - Private corner lot
9.89.8 out of 10 rating
Exceptional
(11 reviews)
King Bed - Entire Home - Private corner lot
Elmhurst, IL
9% off
Price is NZ$3,445
NZ$3,445
NZ$492 per night
includes taxes & fees
Image gallery for Spacious Luxury Retreat 7 Bed Oasis with 5 Baths
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Spacious Luxury Retreat 7 Bed Oasis with 5 Baths
Chicago, Illinois
8% off
Price is NZ$17,100
NZ$17,100
NZ$2,443 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,891
NZ$6,891
NZ$984 per night
includes taxes & fees
Image gallery for Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
Chicago, IL
11% off
Price is NZ$8,290
NZ$8,290
NZ$1,184 per night
includes taxes & fees
Image gallery for BoHo House - A Chic, 1903 Chicago Workers Cottage
1010 out of 10 rating
Exceptional
(10 reviews)
BoHo House - A Chic, 1903 Chicago Workers Cottage
Chicago, IL
12% off
Price is NZ$6,020
NZ$6,020
NZ$860 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
The Avondale Lower Level
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Lovely Riverfront House with Fire Pit & 30ft Swing!
Sleeps 6 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Popular Edgewater Neighborhood.
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
The Tailor House
Sleeps 5 · 2 bedrooms · 0+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Cloud9 | 3XL Penthouses Up to 21 ppl |The Marvelo
Sleeps 21 · 9 bedrooms · 8+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
Sunflower Apt 12 Min from Downtown CHI
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
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