Photo by Khryz Garcia
Chicago holiday homes
We found 491 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Chicago, IL (DPA-Dupage) that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Chicago, IL (DPA-Dupage)
Showing deals for:15 Aug - 22 Aug
Image gallery for Suburban FAB
1010 out of 10 rating
Exceptional
(6 reviews)
Suburban FAB
Schaumburg, IL
9% off
Price is NZ$5,390
NZ$5,390
NZ$770 per night
includes taxes & fees
Image gallery for Re-Designed, Cosmos Retreat, King Bed, Hot Tub, WiFi, Large TVs, Spacious & Calm
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Re-Designed, Cosmos Retreat, King Bed, Hot Tub, WiFi, Large TVs, Spacious & Calm
Bolingbrook, IL
8% off
Price is NZ$10,843
NZ$10,843
NZ$1,549 per night
includes taxes & fees
Image gallery for PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
1010 out of 10 rating
Exceptional
(7 reviews)
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
Aurora, IL
8% off
Price is NZ$4,393
NZ$4,393
NZ$628 per night
includes taxes & fees
Image gallery for Cosmos Stays, Open Space, Jacuzzi, King Beds, Hot Tub, Serene, Spacious
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Cosmos Stays, Open Space, Jacuzzi, King Beds, Hot Tub, Serene, Spacious
Bolingbrook, IL
10% off
Price is NZ$10,619
NZ$10,619
NZ$1,517 per night
includes taxes & fees
Image gallery for Gorgeous, Newly Built Guesthouse In Charming Downtown Geneva!
1010 out of 10 rating
Exceptional
(10 reviews)
Gorgeous, Newly Built Guesthouse In Charming Downtown Geneva!
Geneva, IL
8% off
Price is NZ$3,245
NZ$3,245
NZ$464 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$3,427
NZ$3,427
NZ$490 per night
includes taxes & fees
Image gallery for Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
Bolingbrook, IL
8% off
Price is NZ$7,633
NZ$7,633
NZ$1,090 per night
includes taxes & fees
Image gallery for Exuberant - Elmhurst Home!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Exuberant - Elmhurst Home!
Elmhurst, IL
8% off
Price is NZ$5,198
NZ$5,198
NZ$743 per night
includes taxes & fees
Image gallery for Lovely Riverfront House with Fire Pit & 30ft Swing!
1010 out of 10 rating
Exceptional
(84 reviews)
Lovely Riverfront House with Fire Pit & 30ft Swing!
South Elgin, IL
9% off
Price is NZ$2,826
NZ$2,826
NZ$404 per night
includes taxes & fees
Image gallery for Spacious 4-bedroom vacation home just 1 mile walk to Town and River!
1010 out of 10 rating
Exceptional
(21 reviews)
Spacious 4-bedroom vacation home just 1 mile walk to Town and River!
Geneva, IL
8% off
Price is NZ$5,467
NZ$5,467
NZ$781 per night
includes taxes & fees
Image gallery for PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.89.8 out of 10 rating
Exceptional
(14 reviews)
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle, IL
8% off
Price is NZ$3,176
NZ$3,176
NZ$454 per night
includes taxes & fees
Image gallery for Newly Remodeled Furnished Home In Elmhurst
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Newly Remodeled Furnished Home In Elmhurst
Elmhurst, IL
9% off
Price is NZ$12,123
NZ$12,123
NZ$1,732 per night
includes taxes & fees
Image gallery for Moxie- w/ Game Room- 4 Kings, Sleeps 15
9.09.0 out of 10 rating
Wonderful
(29 reviews)
Moxie- w/ Game Room- 4 Kings, Sleeps 15
Oswego, IL
17% off
Price is NZ$5,932
NZ$5,932
NZ$847 per night
includes taxes & fees
Image gallery for Great Location! Beautiful Home Near Downtown Westmont
1010 out of 10 rating
Exceptional
(7 reviews)
Great Location! Beautiful Home Near Downtown Westmont
Westmont, IL
9% off
Price is NZ$4,957
NZ$4,957
NZ$708 per night
includes taxes & fees
Image gallery for Walk to River & Downtown, Cozy Stay, Grand Porch
1010 out of 10 rating
Exceptional
(7 reviews)
Walk to River & Downtown, Cozy Stay, Grand Porch
St. Charles, Illinois
8% off
Price is NZ$6,938
NZ$6,938
NZ$991 per night
includes taxes & fees
Image gallery for Enjoy your stay at the Train Conductor’s Cottage!
1010 out of 10 rating
Exceptional
(67 reviews)
Enjoy your stay at the Train Conductor’s Cottage!
West Chicago, IL
14% off
Price is NZ$2,553
NZ$2,553
NZ$365 per night
includes taxes & fees
Image gallery for Mini Golf & Game Room + Grill | LCP Collection
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Mini Golf & Game Room + Grill | LCP Collection
Elmhurst, IL
9% off
Price is NZ$4,849
NZ$4,849
NZ$693 per night
includes taxes & fees
Image gallery for PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
1010 out of 10 rating
Exceptional
(41 reviews)
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Wheaton, IL
8% off
Price is NZ$7,436
NZ$7,436
NZ$1,062 per night
includes taxes & fees
Image gallery for PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
1010 out of 10 rating
Exceptional
(23 reviews)
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Streamwood, IL
9% off
Price is NZ$5,598
NZ$5,598
NZ$800 per night
includes taxes & fees
Image gallery for Glen Ellyn Country Side Home
9.29.2 out of 10 rating
Wonderful
(16 reviews)
Glen Ellyn Country Side Home
Glen Ellyn, IL
9% off
Price is NZ$5,517
NZ$5,517
NZ$788 per night
includes taxes & fees
Image gallery for Spacious Home Chicago Suburbs
1010 out of 10 rating
Exceptional
(14 reviews)
Spacious Home Chicago Suburbs
Lombard, IL
6% off
Price is NZ$5,631
NZ$5,631
NZ$804 per night
includes taxes & fees
Image gallery for Hip Urban Loft-Small Town Charm - 124 LOFTS #3
1010 out of 10 rating
Exceptional
(16 reviews)
Hip Urban Loft-Small Town Charm - 124 LOFTS #3
West Dundee, Illinois
6% off
Price is NZ$2,112
NZ$2,112
NZ$302 per night
includes taxes & fees
Image gallery for Family Heaven Retreat, 6 Bedroom, Sleep 16
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Family Heaven Retreat, 6 Bedroom, Sleep 16
Carol Stream, IL
9% off
Price is NZ$8,714
NZ$8,714
NZ$1,245 per night
includes taxes & fees
Image gallery for In the heart of downtown St Charles, IL
9.09.0 out of 10 rating
Wonderful
(6 reviews)
In the heart of downtown St Charles, IL
St. Charles, IL
8% off
Price is NZ$3,296
NZ$3,296
NZ$471 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chicago
Aurora/Naperville - Classy, Spacious Family Home!
Sleeps 12 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The 1840's Goat House
Sleeps 14 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Huge Yard + Patio + King | LCP Collection
Sleeps 10 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Tranquil 4BR in Naperville-Plainfield
Sleeps 12 · 4 bedrooms · 2+ bathrooms
7.47.4 out of 10
Goodgood
10 reviews(10 reviews)
Moxie- w/ Game Room- 4 Kings, Sleeps 15
Sleeps 15 · 5 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
29 reviews(29 reviews)
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
16 reviews(16 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