Chicago holiday homes
We found 3,411 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:15 Aug - 22 Aug
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$8,798
NZ$8,798
NZ$1,257 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
9.69.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$7,056
NZ$7,056
NZ$1,008 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,928
NZ$3,928
NZ$561 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
7% off
Price is NZ$8,415
NZ$8,415
NZ$1,202 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$7,742
NZ$7,742
NZ$1,106 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$3,221
NZ$3,221
NZ$460 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
(33 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,013
NZ$6,013
NZ$859 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$6,724
NZ$6,724
NZ$961 per night
includes taxes & fees
Image gallery for 4BR Lincoln Park Getaway: Steps to Red Line
9.89.8 out of 10 rating
Exceptional
(8 reviews)
4BR Lincoln Park Getaway: Steps to Red Line
Chicago, Illinois
7% off
Price is NZ$7,300
NZ$7,300
NZ$1,043 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$8,749
NZ$8,749
NZ$1,250 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(15 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$11,379
NZ$11,379
NZ$1,626 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
(86 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
8% off
Price is NZ$5,240
NZ$5,240
NZ$749 per night
includes taxes & fees
Image gallery for Best Group/Family Amenities in Downtown|The Cooke
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Best Group/Family Amenities in Downtown|The Cooke
Chicago, IL
8% off
Price is NZ$9,481
NZ$9,481
NZ$1,354 per night
includes taxes & fees
Image gallery for Prime location Historic Chicago Townhouse
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Prime location Historic Chicago Townhouse
Chicago, Illinois
5% off
Price is NZ$17,762
NZ$17,762
NZ$2,537 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(6 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is NZ$6,211
NZ$6,211
NZ$887 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$10,433
NZ$10,433
NZ$1,490 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$4,500
NZ$4,500
NZ$643 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,433
NZ$10,433
NZ$1,490 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,928
NZ$3,928
NZ$561 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,433
NZ$10,433
NZ$1,490 per night
includes taxes & fees
Image gallery for Suburban FAB
1010 out of 10 rating
Exceptional
(6 reviews)
Suburban FAB
Schaumburg, IL
9% off
Price is NZ$5,277
NZ$5,277
NZ$754 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,928
NZ$3,928
NZ$561 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$6,066
NZ$6,066
NZ$867 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,136
NZ$6,136
NZ$877 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
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)
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Sleeps 4 · 25 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sleeps 5 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
25 reviews(25 reviews)
Master qtr close to nature & easy urban facilities
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Your Next Vacation Home
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Spacious 3-bedroom apartment with AC,WiFi in charming Bartlett,free washer/dryer
Sleeps 7 · 3 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
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