4117+ Vacation Rentals Near City Gallery |
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Select Vacation Villas - Vacation Rentals in City Gallery

Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $986
         

10.0 (119 Reviews)
Apartment
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
  • Air Conditioner
  • Parking
  • TV

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Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
Chicago Quick Stay
  • Air Conditioner
  • Pet Friendly
  • Internet

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The Sono Chicago From US $135
         

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10.0 (492 Reviews)
Bed & Breakfast
The Sono Chicago
  • Air Conditioner
  • Parking
  • TV

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3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $264
         

9.6 (27 Reviews)
Apartment
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
  • Air Conditioner
  • Parking
  • TV

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Designer Home in Ukrainian Village - Chicago From US $230
         

10.0 (1 Review)
Apartment
Designer Home in Ukrainian Village - Chicago
  • Air Conditioner
  • Parking
  • Internet

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The Publishing House B&B From US $206
         

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9.8 (195 Reviews)
Bed & Breakfast
The Publishing House B&B
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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52nd Floor MagMile Penthouse Views Fireplace Pool From US $485
         

10.0 (408 Reviews)
Apartment
52nd Floor MagMile Penthouse Views Fireplace Pool
  • Air Conditioner
  • Parking
  • Pool

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New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
New Luxury 3 Bdr Apt in Chicago C9
  • Air Conditioner
  • Parking
  • Pool

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Villa D' Citta From US $242
         

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9.4 (114 Reviews)
Bed & Breakfast
Villa D' Citta
  • Air Conditioner
  • Parking
  • TV

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51st Floor MagMile Penthouse Views Balcony Pool From US $397
         

10.0 (227 Reviews)
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
  • Air Conditioner
  • Parking
  • Pool

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LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY From US $331
         

9.6 (21 Reviews)
Apartment
LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY
  • Air Conditioner
  • Parking
  • TV

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Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC From US $296
         

10.0 (330 Reviews)
Apartment
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
  • Air Conditioner
  • Parking
  • TV

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55th Floor Penthouse with Award-Winning Views From US $1,118
         

10.0 (302 Reviews)
Apartment
55th Floor Penthouse with Award-Winning Views
  • Air Conditioner
  • Parking
  • Pool

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3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place From US $321
         

10.0 (275 Reviews)
Apartment
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
  • Air Conditioner
  • Parking
  • TV

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53 Floor MagMile Penthouse Views, Balcony, Pool From US $516
         

10.0 (244 Reviews)
Apartment
53 Floor MagMile Penthouse Views, Balcony, Pool
  • Air Conditioner
  • Parking
  • Pool

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2-Story Penthouse Views, Fireplace, Pool, Gym From US $865
         

10.0 (212 Reviews)
Apartment
2-Story Penthouse Views, Fireplace, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

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1F Chicago's Little italy Graystone nearDowntown From US $284
         

10.0 (169 Reviews)
Apartment
1F Chicago's Little italy Graystone nearDowntown
  • Air Conditioner
  • Parking
  • TV

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Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,213
         

10.0 (106 Reviews)
Apartment
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
  • Air Conditioner
  • Parking
  • TV

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Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath From US $897
         

10.0 (94 Reviews)
House
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
  • Air Conditioner
  • Parking
  • TV

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Large 4BR/3BA Safe Old Town Location Walk Everywhere From US $950
         

10.0 (74 Reviews)
Apartment
Large 4BR/3BA Safe Old Town Location Walk Everywhere
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lincoln Park Light Filled Loft From US $326
         

10.0 (71 Reviews)
Apartment
Lincoln Park Light Filled Loft
  • Air Conditioner
  • Parking
  • TV

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Private Historic Coach House Wicker Park From US $332
         

10.0 (66 Reviews)
House
Private Historic Coach House Wicker Park
  • Air Conditioner
  • Parking
  • TV

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52nd Floor Penthouse with Skyline Views & Pool From US $376
         

10.0 (64 Reviews)
Apartment
52nd Floor Penthouse with Skyline Views & Pool
  • Air Conditioner
  • Parking
  • Pool

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Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $953
         

10.0 (63 Reviews)
House
Spacious 4-Level/4-Bedroom Townhouse in West Loop
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Selectvacationvillas makes it easy to compare the best listings on Selectvacationvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selectvacationvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in City Gallery.

Weather in City Gallery

View the weather forecast for City Gallery before booking your City Gallery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around City Gallery, IL

Selectvacationvillas offers a large selection of top attractions around City Gallery. Research things to do on your vacation before you visit City Gallery.


Navy Pier Wrigley Field McCormick Place Millennium Park Union Station Soldier Field Willis Tower Art Institute of Chicago United Center Grant Park John G. Shedd Aquarium Chicago Museum of Science and Industry Chicago Theatre Chicago Riverwalk Field Museum of Natural History University of Chicago Brookfield Zoo Northwestern University John Hancock Center Lincoln Park Zoo

City Gallery Vacation Rental Frequently Asked Questions

What are the top vacation rentals in City Gallery?

There are a lot of options in City Gallery. If you plan on staying in the City Gallery area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in City Gallery:

How many vacation rentals are available in City Gallery?

Currently, the total number of properties listed in 2026 is over 4117 in the City Gallery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in City Gallery.