Holiday rentals near City Gallery
We found 3,616 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:17 Oct - 24 Oct
Image gallery for Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
1010 out of 10 rating
Exceptional
(7 reviews)
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
Chicago, IL
7% off
Price is NZ$9,538
NZ$9,538
NZ$1,363 per night
includes taxes & fees
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(14 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
11% off
Price is NZ$7,145
NZ$7,145
NZ$1,021 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
(89 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is NZ$5,390
NZ$5,390
NZ$770 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(13 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$11,226
NZ$11,226
NZ$1,604 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(31 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is NZ$6,268
NZ$6,268
NZ$895 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(9 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$8,592
NZ$8,592
NZ$1,227 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(28 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,224
NZ$4,224
NZ$603 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is NZ$4,783
NZ$4,783
NZ$683 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is NZ$10,415
NZ$10,415
NZ$1,488 per night
includes taxes & fees
Image gallery for Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
1010 out of 10 rating
Exceptional
(16 reviews)
Large, Exquisitely Decorated in Heart of East Lakeview Near Wrigley & Lakefront
Chicago, IL
15% off
Price is NZ$6,132
NZ$6,132
NZ$876 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(40 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,037
NZ$6,037
NZ$862 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$7,399
NZ$7,399
NZ$1,057 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
(5 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is NZ$2,094
NZ$2,094
NZ$299 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, Illinois
7% off
Price is NZ$9,556
NZ$9,556
NZ$1,365 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
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,249
NZ$8,249
NZ$1,178 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, Illinois
7% off
Price is NZ$2,571
NZ$2,571
NZ$367 per night
includes taxes & fees
Image gallery for New Garden Studio near Wrigley/DePaul/Dwtn
9.49.4 out of 10 rating
Exceptional
(15 reviews)
New Garden Studio near Wrigley/DePaul/Dwtn
Chicago, IL
7% off
Price is NZ$3,150
NZ$3,150
NZ$450 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(20 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is NZ$11,826
NZ$11,826
NZ$1,689 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$10,900
NZ$10,900
NZ$1,557 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
(50 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$7,516
NZ$7,516
NZ$1,074 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
(40 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
8% off
Price is NZ$4,068
NZ$4,068
NZ$581 per night
includes taxes & fees
Image gallery for Penthouse Corner 3BR in Streeterville | Roof Deck
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Penthouse Corner 3BR in Streeterville | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,662
NZ$8,662
NZ$1,237 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
(29 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
7% off
Price is NZ$3,181
NZ$3,181
NZ$454 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(31 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,612
NZ$8,612
NZ$1,230 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - City Gallery
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
325 reviews(325 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
441 reviews(441 reviews)
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
77 reviews(77 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.48.4 out of 10
Very goodvery good
321 reviews(321 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
819 reviews(819 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
8.28.2 out of 10
Very goodvery good
114 reviews(114 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