Holiday rentals near Aldo Castillo Gallery
We found 3,698 holiday rentals — enter your dates for availability
Take a look at holiday rentals within easy reach of Aldo Castillo Gallery that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Aldo Castillo Gallery
Showing deals for:21 Nov - 28 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 AU$5,001
AU$5,001
AU$714 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 AU$7,826
AU$7,826
AU$1,118 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 AU$8,019
AU$8,019
AU$1,146 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 AU$5,715
AU$5,715
AU$816 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 AU$6,325
AU$6,325
AU$904 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(28 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is AU$10,826
AU$10,826
AU$1,547 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 AU$6,512
AU$6,512
AU$930 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 AU$2,645
AU$2,645
AU$378 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, IL
8% off
Price is AU$11,682
AU$11,682
AU$1,669 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
7% off
Price is AU$10,537
AU$10,537
AU$1,505 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 AU$2,075
AU$2,075
AU$296 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 AU$4,006
AU$4,006
AU$572 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 AU$1,317
AU$1,317
AU$188 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 AU$2,988
AU$2,988
AU$427 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 AU$5,214
AU$5,214
AU$745 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
(37 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is AU$3,559
AU$3,559
AU$508 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 AU$4,018
AU$4,018
AU$574 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
7% off
Price is AU$1,443
AU$1,443
AU$206 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(17 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is AU$7,819
AU$7,819
AU$1,117 per night
includes taxes & fees
Image gallery for Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
Worth, IL
6% off
Price is AU$3,623
AU$3,623
AU$518 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 AU$5,839
AU$5,839
AU$834 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
8.88.8 out of 10 rating
Excellent
(8 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is AU$2,036
AU$2,036
AU$291 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 AU$8,009
AU$8,009
AU$1,144 per night
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.69.6 out of 10 rating
Exceptional
(17 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
7% off
Price is AU$2,445
AU$2,445
AU$349 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Aldo Castillo Gallery
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
190 reviews(190 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
472 reviews(472 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
338 reviews(338 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
881 reviews(881 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
7.87.8 out of 10
Goodgood
131 reviews(131 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