Chicago holiday rentals
We found 1,818 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:7 Nov - 14 Nov
Image gallery for Hensley’s Cornerstone Lakehouse
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Hensley’s Cornerstone Lakehouse
Wauconda, IL
8% off
Price is S$4,053
S$4,053
S$579 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
6% off
Price is S$2,507
S$2,507
S$358 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
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
14% off
Price is S$2,869
S$2,869
S$410 per night
includes taxes & fees
Image gallery for Family frndly TwnHm by navy base
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Family frndly TwnHm by navy base
Waukegan, IL
16% off
Price is S$1,824
S$1,824
S$261 per night
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
7% off
Price is S$4,375
S$4,375
S$625 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.69.6 out of 10 rating
Exceptional
(35 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is S$2,634
S$2,634
S$376 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house in Grayslake
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Charming 3-bedroom house in Grayslake
Grayslake, IL
8% off
Price is S$3,153
S$3,153
S$450 per night
includes taxes & fees
Image gallery for great home in Waukegan for navy graduate families close distance to navy base!!
9.69.6 out of 10 rating
Exceptional
(28 reviews)
great home in Waukegan for navy graduate families close distance to navy base!!
Waukegan, IL
8% off
Price is S$2,872
S$2,872
S$410 per night
includes taxes & fees
Image gallery for 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
9.09.0 out of 10 rating
Wonderful
(9 reviews)
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan, IL
8% off
Price is S$1,867
S$1,867
S$267 per night
includes taxes & fees
Image gallery for Roxan Corner
8.68.6 out of 10 rating
Excellent
(37 reviews)
Roxan Corner
Mundelein, IL
8% off
Price is S$1,958
S$1,958
S$280 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 S$2,037
S$2,037
S$291 per night
includes taxes & fees
Image gallery for Beautiful Huge Lakefront Remodeled Home with Incredible Views
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Round Lake, IL
8% off
Price is S$3,073
S$3,073
S$439 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
7% off
Price is S$1,709
S$1,709
S$244 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
(61 reviews)
IVP Manor House Close to Lake, Beach & Naval Base
Grayslake, IL
8% off
Price is S$4,178
S$4,178
S$597 per night
includes taxes & fees
Image gallery for NEW LUXURY CONDO WITH PATIO DECK
1010 out of 10 rating
Exceptional
(175 reviews)
NEW LUXURY CONDO WITH PATIO DECK
Chicago, IL
10% off
Price is S$2,562
S$2,562
S$366 per night
includes taxes & fees
Image gallery for Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
9.89.8 out of 10 rating
Exceptional
(115 reviews)
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Lake Forest, IL
13% off
Price is S$3,546
S$3,546
S$507 per night
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square
8.48.4 out of 10 rating
Very good
(11 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
5% off
Price is S$1,627
S$1,627
S$232 per night
includes taxes & fees
Image gallery for Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.09.0 out of 10 rating
Wonderful
(32 reviews)
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
North Chicago, IL
16% off
Price is S$1,599
S$1,599
S$228 per night
includes taxes & fees
Image gallery for Cheerful 3 bedroom. Feels like home.
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Cheerful 3 bedroom. Feels like home.
Chicago, IL
14% off
Price is S$2,291
S$2,291
S$327 per night
includes taxes & fees
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
7% off
Price is S$3,417
S$3,417
S$488 per night
includes taxes & fees
Image gallery for ❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
9.69.6 out of 10 rating
Exceptional
(35 reviews)
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Chicago, IL
11% off
Price is S$5,898
S$5,898
S$843 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
(30 reviews)
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Gurnee, IL
13% off
Price is S$4,688
S$4,688
S$670 per night
includes taxes & fees
Image gallery for Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Gurnee, IL
16% off
Price is S$3,494
S$3,494
S$499 per night
includes taxes & fees
Image gallery for Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
1010 out of 10 rating
Exceptional
(14 reviews)
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
Evanston, IL
11% off
Price is S$2,144
S$2,144
S$306 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
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Chalet
Find the best place to stay - Chicago
Spacious Budget-friendly Room w/ Kitchenette Ideal for Extended or Short Stays
Sleeps 2 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Huge 4BR w/ Yard | Sleeps 8 | LCP Collection
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Indulge In Home Like Comfort! Near Genesee Theater, Pets Allowed, Outdoor Pool!
Sleeps 3 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
Free Parking, Private Terrace Up to 10%off on 30day stay
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
Top rated rentals - Chicago
Great for bonding, cute neighbourhood
1010 out of 10
Exceptionalexceptional
185 reviews(185 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