Chicago holiday homes
We found 3,770 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Chicago Midway Airport (MDW) that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago, IL (MDW-Midway Intl.)
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 NZ$7,197
NZ$7,197
NZ$1,028 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 NZ$5,446
NZ$5,446
NZ$778 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 NZ$10,959
NZ$10,959
NZ$1,566 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 NZ$7,604
NZ$7,604
NZ$1,086 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 NZ$10,473
NZ$10,473
NZ$1,496 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(40 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,100
NZ$6,100
NZ$871 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 NZ$7,897
NZ$7,897
NZ$1,128 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 NZ$6,333
NZ$6,333
NZ$905 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 NZ$4,267
NZ$4,267
NZ$610 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 NZ$8,112
NZ$8,112
NZ$1,159 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
7% off
Price is NZ$9,604
NZ$9,604
NZ$1,372 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is NZ$5,211
NZ$5,211
NZ$744 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 NZ$7,565
NZ$7,565
NZ$1,081 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 NZ$6,195
NZ$6,195
NZ$885 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 NZ$5,970
NZ$5,970
NZ$853 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$10,570
NZ$10,570
NZ$1,510 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 NZ$11,968
NZ$11,968
NZ$1,710 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 NZ$8,633
NZ$8,633
NZ$1,233 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is NZ$2,115
NZ$2,115
NZ$302 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 NZ$2,596
NZ$2,596
NZ$371 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 NZ$3,245
NZ$3,245
NZ$464 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 NZ$2,869
NZ$2,869
NZ$410 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 NZ$4,110
NZ$4,110
NZ$587 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
(29 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is NZ$3,214
NZ$3,214
NZ$459 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
Hidden Gem OASIS 40 minutes away from Chicago
Sleeps 8 · 4 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
Relax in style: Chic 2 bedroom haven in brickell.
Sleeps 4 · 2 bedrooms · 1 bathroom
3.03.0 out of 10
2 reviews(2 reviews)
Small hidden Gem
Sleeps 4 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
8 reviews(8 reviews)
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Sleeps 5 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
566 reviews(566 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