Holiday rentals near City Gallery
We found 3,658 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of City Gallery. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a TV. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - City Gallery
Showing deals for:20 Mar - 27 Mar
Image gallery for Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.29.2 out of 10, Wonderful, (61 reviews)
Wonderful
(61 reviews)
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Chicago
7% off
Price is NZ$7,536
NZ$7,536
for 7 nights, 1 home
NZ$1,077 per night
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago
16% off
Price is NZ$41,154
NZ$41,154
for 7 nights, 1 home
NZ$5,879 per night
includes taxes & fees
Image gallery for BoHo House - A Chic, 1903 Chicago Workers Cottage
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
BoHo House - A Chic, 1903 Chicago Workers Cottage
Chicago
11% off
Price is NZ$5,437
NZ$5,437
for 7 nights, 1 home
NZ$777 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, Exceptional, (69 reviews)
Exceptional
(69 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago
7% off
Price is NZ$5,365
NZ$5,365
for 7 nights, 1 home
NZ$766 per night
includes taxes & fees
Image gallery for Luxurious, custom built single family home near Wrigley
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Luxurious, custom built single family home near Wrigley
Chicago
7% off
Price is NZ$17,059
NZ$17,059
for 7 nights, 1 home
NZ$2,437 per night
includes taxes & fees
Image gallery for 4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.29.2 out of 10, Wonderful, (13 reviews)
Wonderful
(13 reviews)
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
11% off
Price is NZ$6,055
NZ$6,055
for 7 nights, 1 home
NZ$865 per night
includes taxes & fees
Image gallery for Newly Remodeled Furnished Home In Elmhurst
9.89.8 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Newly Remodeled Furnished Home In Elmhurst
Elmhurst
9% off
Price is NZ$12,912
NZ$12,912
for 7 nights, 1 home
NZ$1,845 per night
includes taxes & fees
Image gallery for Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Chicago
7% off
Price is NZ$3,441
NZ$3,441
for 7 nights, 1 apartment
NZ$492 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.88.8 out of 10, Excellent, (15 reviews)
Excellent
(15 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago
7% off
Price is NZ$7,257
NZ$7,257
for 7 nights, 1 apartment
NZ$1,037 per night
includes taxes & fees
Image gallery for Ridgeland Retreat/ Street level Apt easy access
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
Ridgeland Retreat/ Street level Apt easy access
Berwyn
8% off
Price is NZ$3,384
NZ$3,384
for 7 nights, 1 apartment
NZ$483 per night
includes taxes & fees
Image gallery for Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
9.89.8 out of 10, Exceptional, (182 reviews)
Exceptional
(182 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
14% off
Price is NZ$7,303
NZ$7,303
for 7 nights, 1 home
NZ$1,043 per night
includes taxes & fees
Image gallery for Quick Access to O'Hare and Chicago downtown
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Quick Access to O'Hare and Chicago downtown
Melrose Park
8% off
Price is NZ$4,241
NZ$4,241
for 7 nights, 1 home
NZ$606 per night
includes taxes & fees
Image gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
9.89.8 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
7% off
Price is NZ$17,752
NZ$17,752
for 7 nights, 1 apartment
NZ$2,536 per night
includes taxes & fees
Image gallery for The Avondale Guesthouse
9.89.8 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
The Avondale Guesthouse
Chicago
14% off
Price is NZ$2,923
NZ$2,923
for 7 nights, 1 home
NZ$418 per night
includes taxes & fees
Image gallery for Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
Chicago
7% off
Price is NZ$5,642
NZ$5,642
for 7 nights, 1 apartment
NZ$806 per night
includes taxes & fees
Image gallery for 4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
9% off
Price is NZ$6,218
NZ$6,218
for 7 nights, 1 apartment
NZ$888 per night
includes taxes & fees
Image gallery for 1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago
7% off
Price is NZ$6,005
NZ$6,005
for 7 nights, 1 home
NZ$858 per night
includes taxes & fees
Image gallery for Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking
Chicago
14% off
Price is NZ$3,016
NZ$3,016
for 7 nights, 1 apartment
NZ$431 per night
includes taxes & fees
Image gallery for Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
8.68.6 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Chicago
7% off
Price is NZ$11,580
NZ$11,580
for 7 nights, 1 home
NZ$1,654 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago
6% off
Price is NZ$2,866
NZ$2,866
for 7 nights, 1 apartment
NZ$409 per night
includes taxes & fees
Image gallery for Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
Chicago
7% off
Price is NZ$5,504
NZ$5,504
for 7 nights, 1 apartment
NZ$786 per night
includes taxes & fees
Image gallery for Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions
9.29.2 out of 10, Wonderful, (14 reviews)
Wonderful
(14 reviews)
Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions
Des Plaines
9% off
Price is NZ$4,857
NZ$4,857
for 7 nights, 1 home
NZ$694 per night
includes taxes & fees
Image gallery for Gorgeous 7BD Home
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Gorgeous 7BD Home
Chicago
7% off
Price is NZ$12,361
NZ$12,361
for 7 nights, 1 home
NZ$1,766 per night
includes taxes & fees
Image gallery for Home Away From Home
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Home Away From Home
Chicago
11% off
Price is NZ$4,708
NZ$4,708
for 7 nights, 1 home
NZ$673 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - City Gallery
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
1,009 reviews(1,009 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
401 reviews(401 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
650 reviews(650 reviews)
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.69.6 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
NEW LUXURY PENTHOUSE CONDO
Sleeps 9 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
390 reviews(390 reviews)
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