Photo by Eleonora Bertacchi
Holiday rentals near Oak Street
We found 3,087 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Oak Street. Holiday rentals offer the best amenities for your family, friends or furry companion, such as air conditioning and a pool. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Oak Street
Showing deals for:21 Nov - 28 Nov
Image gallery for Downtown Charm: 2BR, Comfort, Great Amenities
1010 out of 10 rating
Exceptional
(6 reviews)
Downtown Charm: 2BR, Comfort, Great Amenities
Chicago, IL
7% off
Price is NZ$7,393
NZ$7,393
NZ$1,056 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
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is NZ$5,509
NZ$5,509
NZ$787 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
7% off
Price is NZ$8,870
NZ$8,870
NZ$1,267 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
7% off
Price is NZ$8,660
NZ$8,660
NZ$1,237 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
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is NZ$6,292
NZ$6,292
NZ$899 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
(58 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
7% off
Price is NZ$6,921
NZ$6,921
NZ$989 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.29.2 out of 10 rating
Wonderful
(35 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is NZ$7,125
NZ$7,125
NZ$1,018 per night
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
7% off
Price is NZ$2,930
NZ$2,930
NZ$419 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, IL
7% off
Price is NZ$10,898
NZ$10,898
NZ$1,557 per night
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
14% off
Price is NZ$2,314
NZ$2,314
NZ$331 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
(29 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
7% off
Price is NZ$4,630
NZ$4,630
NZ$661 per night
includes taxes & fees
Image gallery for Studio flat in the heart of Chicago's Gold Coast
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Studio flat in the heart of Chicago's Gold Coast
Chicago, IL
5% off
Price is NZ$1,446
NZ$1,446
NZ$207 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,713
NZ$4,713
NZ$673 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, IL
7% off
Price is NZ$2,758
NZ$2,758
NZ$394 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 NZ$3,296
NZ$3,296
NZ$471 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 NZ$5,747
NZ$5,747
NZ$821 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
(36 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,923
NZ$3,923
NZ$560 per night
includes taxes & fees
Image gallery for Trendy|Comfortable|1BR|Lincoln Square
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Trendy|Comfortable|1BR|Lincoln Square
Chicago, IL
7% off
Price is NZ$4,429
NZ$4,429
NZ$633 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is NZ$8,546
NZ$8,546
NZ$1,221 per night
includes taxes & fees
Image gallery for Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
8.68.6 out of 10 rating
Excellent
(9 reviews)
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
Chicago, IL
6% off
Price is NZ$1,607
NZ$1,607
NZ$230 per night
includes taxes & fees
Image gallery for Stylish Corner 2BR in the Loop | City & Lake Views
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Stylish Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is NZ$6,399
NZ$6,399
NZ$914 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is NZ$8,753
NZ$8,753
NZ$1,250 per night
includes taxes & fees
Image gallery for Modern|Aesthetic|2BR|Evanston|Next to Beach
8.68.6 out of 10 rating
Excellent
(22 reviews)
Modern|Aesthetic|2BR|Evanston|Next to Beach
Evanston, IL
8% off
Price is NZ$5,018
NZ$5,018
NZ$717 per night
includes taxes & fees
Image gallery for ⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
9.69.6 out of 10 rating
Exceptional
(8 reviews)
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Chicago, IL
7% off
Price is NZ$5,317
NZ$5,317
NZ$760 per night
includes taxes & fees
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Find the best place to stay - Oak Street
Cheerful 4 bedroom smart home w/ indoor fireplace
Sleeps 12 · 4 bedrooms · 3+ bathrooms
8.08.0 out of 10
Very goodvery good
14 reviews(14 reviews)
Cozy Room with Rooftop Lounge & City Views in River North
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Luxury Designer Penthouse | Gold Coast/Old Town
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 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