Chicago holiday rentals
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 AU$6,997
AU$6,997
AU$1,000 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 AU$4,531
AU$4,531
AU$647 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 AU$2,739
AU$2,739
AU$391 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 AU$2,568
AU$2,568
AU$367 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 AU$1,971
AU$1,971
AU$282 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
8% off
Price is AU$3,767
AU$3,767
AU$538 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 AU$4,141
AU$4,141
AU$592 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 AU$2,693
AU$2,693
AU$385 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
9% off
Price is AU$2,985
AU$2,985
AU$426 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 AU$2,374
AU$2,374
AU$339 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 AU$9,812
AU$9,812
AU$1,402 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 AU$5,141
AU$5,141
AU$734 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 AU$4,676
AU$4,676
AU$668 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 AU$5,681
AU$5,681
AU$812 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 AU$3,381
AU$3,381
AU$483 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 AU$2,150
AU$2,150
AU$307 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 AU$2,273
AU$2,273
AU$325 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
8% off
Price is AU$14,075
AU$14,075
AU$2,011 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 AU$3,143
AU$3,143
AU$449 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 AU$9,530
AU$9,530
AU$1,361 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 AU$4,208
AU$4,208
AU$601 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 AU$4,394
AU$4,394
AU$628 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 AU$6,165
AU$6,165
AU$881 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 AU$2,951
AU$2,951
AU$422 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
Showing deals for: 3 Oct - 6 Oct
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
The current price is AU$5,351
AU$5,351
for 3 nights, 1 room
AU$1,784 per night
includes taxes & fees
Modern 3Bd Townhome Near Beach & Base
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
The current price is AU$1,945
AU$1,945
for 3 nights, 1 home
AU$648 per night
includes taxes & fees
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)
The current price is AU$1,014
AU$1,014
for 3 nights, 1 apartment
AU$338 per night
includes taxes & fees
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)
The current price is AU$682
AU$682
for 3 nights, 1 home
AU$227 per night
includes taxes & fees
"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)
The current price is AU$508
AU$508
for 3 nights, 1 home
AU$169 per night
includes taxes & fees
Flexhome Wicker Park 2BR DV3
Sleeps 5 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
The current price is AU$2,103
AU$2,103
for 3 nights, 1 apartment
AU$701 per night
includes taxes & fees
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