Chicago holiday lettings
We found 1,681 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:25 Jul - 1 Aug
Image gallery for Suburban FAB
1010 out of 10 rating
Exceptional
(6 reviews)
Suburban FAB
Schaumburg, IL
9% off
Price is £3,597
£3,597
£514 per night
includes taxes & fees
Image gallery for SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
9.89.8 out of 10 rating
Exceptional
(80 reviews)
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Chicago, IL
8% off
Price is £4,150
£4,150
£593 per night
includes taxes & fees
Image gallery for "Holy Cow"! 4bed 4bath Duplex Penthouse w/ 3,000 sqft Private Roof-Deck!
9.69.6 out of 10 rating
Exceptional
(45 reviews)
"Holy Cow"! 4bed 4bath Duplex Penthouse w/ 3,000 sqft Private Roof-Deck!
Chicago, IL
16% off
Price is £8,740
£8,740
£1,249 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home
1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
11% off
Price is £4,353
£4,353
£622 per night
includes taxes & fees
Image gallery for Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
Chicago, IL
7% off
Price is £3,408
£3,408
£487 per night
includes taxes & fees
Image gallery for 3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
1010 out of 10 rating
Exceptional
(22 reviews)
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
Chicago, IL
12% off
Price is £3,840
£3,840
£549 per night
includes taxes & fees
Image gallery for A quiet stay while you are away
9.89.8 out of 10 rating
Exceptional
(32 reviews)
A quiet stay while you are away
Oak Park, IL
8% off
Price is £1,540
£1,540
£220 per night
includes taxes & fees
Image gallery for NEW! 10-min to Downtown | LCP Collection
9.69.6 out of 10 rating
Exceptional
(8 reviews)
NEW! 10-min to Downtown | LCP Collection
Oak Park, IL
9% off
Price is £4,310
£4,310
£616 per night
includes taxes & fees
Image gallery for Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
1010 out of 10 rating
Exceptional
(8 reviews)
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Chicago, IL
11% off
Price is £4,076
£4,076
£582 per night
includes taxes & fees
Image gallery for Spacious Deck & Balcony, Game Area, Garage
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Spacious Deck & Balcony, Game Area, Garage
Glen Ellyn, IL
8% off
Price is £3,951
£3,951
£564 per night
includes taxes & fees
Image gallery for Large house in Chicago suburb
1010 out of 10 rating
Exceptional
(6 reviews)
Large house in Chicago suburb
Skokie, IL
17% off
Price is £4,589
£4,589
£656 per night
includes taxes & fees
Image gallery for Spacious Downtown Forest Park Retreat
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spacious Downtown Forest Park Retreat
Forest Park, IL
33% off
Price is £4,684
£4,684
£669 per night
includes taxes & fees
Image gallery for Luxury Retreat with Home Theater
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Luxury Retreat with Home Theater
Chicago, Illinois
8% off
Price is £8,093
£8,093
£1,156 per night
includes taxes & fees
Image gallery for The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
9.69.6 out of 10 rating
Exceptional
(163 reviews)
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Chicago, IL
23% off
Price is £3,696
£3,696
£528 per night
includes taxes & fees
Image gallery for ☆King Bed/3 bds Home near Naval Base - 6Flags - Casino☆
1010 out of 10 rating
Exceptional
(15 reviews)
☆King Bed/3 bds Home near Naval Base - 6Flags - Casino☆
Waukegan, IL
9% off
Price is £1,752
£1,752
£250 per night
includes taxes & fees
Image gallery for Large 2-Bedroom w/ Huge Roofdeck view of Skyline
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Chicago, IL
8% off
Price is £2,823
£2,823
£403 per night
includes taxes & fees
Image gallery for ☆2bdrm Apt near Naval Base - 6 Flags - Casino☆
1010 out of 10 rating
Exceptional
(25 reviews)
☆2bdrm Apt near Naval Base - 6 Flags - Casino☆
Waukegan, IL
8% off
Price is £1,604
£1,604
£229 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 £5,469
£5,469
£781 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Chicago, IL
7% off
Price is £2,165
£2,165
£309 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
8% off
Price is £5,018
£5,018
£717 per night
includes taxes & fees
Image gallery for Spacious Home Chicago Suburbs
1010 out of 10 rating
Exceptional
(11 reviews)
Spacious Home Chicago Suburbs
Lombard, IL
6% off
Price is £3,960
£3,960
£566 per night
includes taxes & fees
Image gallery for Modern 3BR Apartment Near Navy Base And Six Flags.
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Modern 3BR Apartment Near Navy Base And Six Flags.
North Chicago, IL
8% off
Price is £1,379
£1,379
£197 per night
includes taxes & fees
Image gallery for One Bedroom - Suite.
1010 out of 10 rating
Exceptional
(16 reviews)
One Bedroom - Suite.
Hoffman Estates, IL
8% off
Price is £618
£618
£88 per night
includes taxes & fees
Image gallery for Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Chicago, IL
15% off
Price is £2,453
£2,453
£350 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chicago
-Lovely 5 BedRoom Unit in Uptown
Sleeps 14 · 5 bedrooms · 3 bathrooms
Flexhome Wicker Park 2BR DV3
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
Best Lincoln Square Location - Spacious 2 bedroom
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Quaint Bungalow, near Great Lakes Naval Base
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Top rated rentals - Chicago
Very good
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Lovely property near Wrigley
1010 out of 10
Exceptionalexceptional
26 reviews(26 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value