Holiday rentals near Joseph J. Gentile Center
We found 3,625 holiday rentals — enter your dates for availability
Choose the right holiday home within easy reach of Joseph J. Gentile Center. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as parking and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Joseph J. Gentile Center
Showing deals for:14 Nov - 21 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 NZ$5,512
NZ$5,512
NZ$787 nightly
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 NZ$8,757
NZ$8,757
NZ$1,251 nightly
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$5,590
NZ$5,590
NZ$799 nightly
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$6,170
NZ$6,170
NZ$881 nightly
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$5,371
NZ$5,371
NZ$767 nightly
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$5,946
NZ$5,946
NZ$849 nightly
Includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
7% off
Price is NZ$11,072
NZ$11,072
NZ$1,582 nightly
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 NZ$4,394
NZ$4,394
NZ$628 nightly
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
6% off
Price is NZ$2,163
NZ$2,163
NZ$309 nightly
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
13% off
Price is NZ$1,823
NZ$1,823
NZ$260 nightly
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$3,298
NZ$3,298
NZ$471 nightly
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$5,750
NZ$5,750
NZ$821 nightly
Includes taxes & fees
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
7% off
Price is NZ$4,498
NZ$4,498
NZ$643 nightly
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$7,562
NZ$7,562
NZ$1,080 nightly
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$5,485
NZ$5,485
NZ$784 nightly
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 NZ$2,245
NZ$2,245
NZ$321 nightly
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 NZ$5,256
NZ$5,256
NZ$751 nightly
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$7,743
NZ$7,743
NZ$1,106 nightly
Includes taxes & fees
Image gallery for Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
1010 out of 10 rating
Exceptional
(23 reviews)
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
Chicago (and vicinity), IL
13% off
Price is NZ$3,726
NZ$3,726
NZ$532 nightly
Includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$7,641
NZ$7,641
NZ$1,092 nightly
Includes taxes & fees
Image gallery for Stunning 3BR Penthouse in the Loop | Roof Deck
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Stunning 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is NZ$7,851
NZ$7,851
NZ$1,122 nightly
Includes taxes & fees
Image gallery for 3BR Prime Hyde Park Location Near University of Chicago and Dining
1010 out of 10 rating
Exceptional
(7 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Chicago, IL
5% off
Price is NZ$3,867
NZ$3,867
NZ$552 nightly
Includes taxes & fees
Image gallery for Stunning Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is NZ$5,191
NZ$5,191
NZ$742 nightly
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 NZ$2,138
NZ$2,138
NZ$305 nightly
Includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Joseph J. Gentile Center
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
470 reviews(470 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
338 reviews(338 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
189 reviews(189 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
83 reviews(83 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
875 reviews(875 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
7.87.8 out of 10
Goodgood
129 reviews(129 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