Holiday rentals near Wood Street Gallery
We found 3,723 holiday rentals — enter your dates for availability
Choose the right holiday rental within close proximity to Wood Street Gallery. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Wood Street Gallery
Showing deals for:7 Nov - 14 Nov
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 S$4,186
S$4,186
S$598 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
7% off
Price is S$6,965
S$6,965
S$995 per night
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
21% off
Price is S$28,417
S$28,417
S$4,060 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 S$4,607
S$4,607
S$658 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, IL
8% off
Price is S$3,863
S$3,863
S$552 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 S$5,489
S$5,489
S$784 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
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
7% off
Price is S$5,239
S$5,239
S$748 per night
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is S$6,737
S$6,737
S$962 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
7% off
Price is S$4,042
S$4,042
S$577 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, IL
7% off
Price is S$5,037
S$5,037
S$720 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$2,502
S$2,502
S$357 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is S$1,612
S$1,612
S$230 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$2,863
S$2,863
S$409 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is S$2,332
S$2,332
S$333 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
(33 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is S$2,628
S$2,628
S$375 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is S$7,033
S$7,033
S$1,005 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$2,033
S$2,033
S$290 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$1,706
S$1,706
S$244 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is S$3,990
S$3,990
S$570 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is S$6,617
S$6,617
S$945 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is S$1,705
S$1,705
S$244 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 S$4,706
S$4,706
S$672 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 S$6,560
S$6,560
S$937 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.68.6 out of 10 rating
Excellent
(13 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
7% off
Price is S$2,310
S$2,310
S$330 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wood Street Gallery
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
461 reviews(461 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
337 reviews(337 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
82 reviews(82 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
183 reviews(183 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
864 reviews(864 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
340 reviews(340 reviews)
Top rated rentals - Wood Street Gallery
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