Chicago holiday homes
We found 1,800 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals close to Chicago, IL (PWK-Chicago Executive) that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a fireplace. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago, IL (PWK-Chicago Executive)
Showing deals for:3 Oct - 10 Oct
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$7,750
NZ$7,750
NZ$1,107 per night
includes taxes & fees
Image gallery for Hensley’s Cornerstone Lakehouse
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Hensley’s Cornerstone Lakehouse
Wauconda, IL
9% off
Price is NZ$4,911
NZ$4,911
NZ$702 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is NZ$2,977
NZ$2,977
NZ$425 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$2,793
NZ$2,793
NZ$399 per night
includes taxes & fees
Image gallery for Family frndly TwnHm by navy base
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Family frndly TwnHm by navy base
Waukegan, IL
12% off
Price is NZ$2,113
NZ$2,113
NZ$302 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
(38 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
7% off
Price is NZ$4,096
NZ$4,096
NZ$585 per night
includes taxes & fees
Image gallery for Beautiful Huge Lakefront Remodeled Home with Incredible Views
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Round Lake, IL
8% off
Price is NZ$4,498
NZ$4,498
NZ$643 per night
includes taxes & fees
Image gallery for Little Fox Cottage - A Cozy Riverview Getaway
1010 out of 10 rating
Exceptional
(15 reviews)
Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove, IL
8% off
Price is NZ$2,925
NZ$2,925
NZ$418 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
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,242
NZ$3,242
NZ$463 per night
includes taxes & fees
Image gallery for Charming 3-bedroom apartment with AC and WiFi in Waukegan.
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Waukegan, IL
8% off
Price is NZ$2,549
NZ$2,549
NZ$364 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
7% off
Price is NZ$10,563
NZ$10,563
NZ$1,509 per night
includes taxes & fees
Image gallery for IVP Manor House Close to Lake, Beach & Naval Base
9.69.6 out of 10 rating
Exceptional
(57 reviews)
IVP Manor House Close to Lake, Beach & Naval Base
Grayslake, IL
8% off
Price is NZ$5,583
NZ$5,583
NZ$798 per night
includes taxes & fees
Image gallery for Pet Friendly Huge Lake Front Home with Stunning Views
9.69.6 out of 10 rating
Exceptional
(45 reviews)
Pet Friendly Huge Lake Front Home with Stunning Views
Round Lake, IL
8% off
Price is NZ$5,078
NZ$5,078
NZ$725 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
33% off
Price is NZ$6,155
NZ$6,155
NZ$879 per night
includes taxes & fees
Image gallery for Suburban FAB
1010 out of 10 rating
Exceptional
(7 reviews)
Suburban FAB
Schaumburg, IL
9% off
Price is NZ$3,679
NZ$3,679
NZ$526 per night
includes taxes & fees
Image gallery for Home Sweet Home
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Home Sweet Home
Chicago, IL
7% off
Price is NZ$2,293
NZ$2,293
NZ$328 per night
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square
8.28.2 out of 10 rating
Very good
(10 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
5% off
Price is NZ$2,439
NZ$2,439
NZ$348 per night
includes taxes & fees
Image gallery for Wrigleyville Jungle House w/ game room basement party room for large groups!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Wrigleyville Jungle House w/ game room basement party room for large groups!
Chicago, IL
7% off
Price is NZ$15,855
NZ$15,855
NZ$2,265 per night
includes taxes & fees
Image gallery for PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
9.69.6 out of 10 rating
Exceptional
(10 reviews)
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard, IL
8% off
Price is NZ$3,462
NZ$3,462
NZ$495 per night
includes taxes & fees
Image gallery for Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
Chicago, IL
7% off
Price is NZ$10,265
NZ$10,265
NZ$1,466 per night
includes taxes & fees
Image gallery for Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Gurnee, IL
16% off
Price is NZ$4,571
NZ$4,571
NZ$653 per night
includes taxes & fees
Image gallery for Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib
Chicago, IL
19% off
Price is NZ$4,768
NZ$4,768
NZ$681 per night
includes taxes & fees
Image gallery for Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Gurnee, IL
13% off
Price is NZ$6,668
NZ$6,668
NZ$953 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom in ideal Roscoe village location
1010 out of 10 rating
Exceptional
(45 reviews)
Spacious 3 bedroom in ideal Roscoe village location
Chicago, IL
7% off
Price is NZ$3,205
NZ$3,205
NZ$458 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Modern 3Bd Townhome Near Beach & Base
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sleeps 5 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
28 reviews(28 reviews)
Spacious Budget-friendly Room w/ Kitchenette Ideal for Extended or Short Stays
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Sleeps 4 · 25 bedrooms · 1 bathroom
5.25.2 out of 10
5 reviews(5 reviews)
Flexhome Wicker Park 2BR DV3
Sleeps 5 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 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