Holiday rentals near City Gallery
We found 3,343 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:15 Aug - 22 Aug
Image gallery for Chic 2BR 2BA Condo with Balcony - River North Chicago
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Chic 2BR 2BA Condo with Balcony - River North Chicago
Chicago, Illinois
8% off
Price is NZ$8,830
NZ$8,830
NZ$1,261 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
9.69.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$7,019
NZ$7,019
NZ$1,003 per night
includes taxes & fees
Image gallery for 1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul
9.69.6 out of 10 rating
Exceptional
(11 reviews)
1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul
Chicago, Illinois
8% off
Price is NZ$11,123
NZ$11,123
NZ$1,589 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,952
NZ$3,952
NZ$565 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$8,131
NZ$8,131
NZ$1,162 per night
includes taxes & fees
Image gallery for Why Guests Call This Chicago’s Best Spot|TheViolet
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Why Guests Call This Chicago’s Best Spot|TheViolet
Chicago, Illinois
7% off
Price is NZ$7,612
NZ$7,612
NZ$1,087 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$8,112
NZ$8,112
NZ$1,159 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,247
NZ$3,247
NZ$464 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$5,963
NZ$5,963
NZ$852 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(226 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,666
NZ$6,666
NZ$952 per night
includes taxes & fees
Image gallery for 4BR Lincoln Park Getaway: Steps to Red Line
9.89.8 out of 10 rating
Exceptional
(8 reviews)
4BR Lincoln Park Getaway: Steps to Red Line
Chicago, Illinois
7% off
Price is NZ$7,272
NZ$7,272
NZ$1,039 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
(46 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,012
NZ$6,012
NZ$859 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(15 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$11,406
NZ$11,406
NZ$1,629 per night
includes taxes & fees
Image gallery for Why Settle for Ordinary?5 Stars Apartment|The Avant
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Why Settle for Ordinary?5 Stars Apartment|The Avant
Chicago, Illinois
8% off
Price is NZ$7,832
NZ$7,832
NZ$1,119 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
(86 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
8% off
Price is NZ$5,205
NZ$5,205
NZ$744 per night
includes taxes & fees
Image gallery for Best Group/Family Amenities in Downtown|The Cooke
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Best Group/Family Amenities in Downtown|The Cooke
Chicago, IL
8% off
Price is NZ$9,153
NZ$9,153
NZ$1,308 per night
includes taxes & fees
Image gallery for Prime location Historic Chicago Townhouse
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Prime location Historic Chicago Townhouse
Chicago, Illinois
5% off
Price is NZ$17,762
NZ$17,762
NZ$2,537 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,501
NZ$4,501
NZ$643 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,374
NZ$10,374
NZ$1,482 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,952
NZ$3,952
NZ$565 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,247
NZ$3,247
NZ$464 per night
includes taxes & fees
Image gallery for Cloud9 |up to 14ppl Terrace @MagMile|The Artemis
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Cloud9 |up to 14ppl Terrace @MagMile|The Artemis
Chicago, Illinois
8% off
Price is NZ$19,272
NZ$19,272
NZ$2,753 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(6 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is NZ$6,440
NZ$6,440
NZ$920 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,087
NZ$6,087
NZ$870 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - City Gallery
Showing deals for: 12 Aug - 15 Aug
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
69 reviews(69 reviews)
The current price is NZ$1,340
NZ$1,340
for 3 nights, 1 home
NZ$447 per night
includes taxes & fees
Sonder Onterie
Sleeps 2 · 1 bedroom
8.48.4 out of 10
Very goodvery good
15 reviews(15 reviews)
The current price is NZ$968
NZ$968
for 3 nights, 1 apartment
NZ$323 per night
includes taxes & fees
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
313 reviews(313 reviews)
The current price is NZ$1,560
NZ$1,560
for 3 nights, 1 room
NZ$520 per night
includes taxes & fees
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
281 reviews(281 reviews)
The current price is NZ$822
NZ$822
for 3 nights, 1 room
NZ$274 per night
includes taxes & fees
Sonder The Opal
Sleeps 6 · 2 bedrooms
8.68.6 out of 10
Excellentexcellent
36 reviews(36 reviews)
The current price is NZ$1,161
NZ$1,161
for 3 nights, 1 room
NZ$387 per night
includes taxes & fees
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
401 reviews(401 reviews)
The current price is NZ$1,237
NZ$1,237
for 3 nights, 1 room
NZ$412 per night
includes taxes & fees
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