4285+ Vacation Rentals Near Chicago Theatre |
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Sell Off Cruises - Vacation Rentals in Chicago Theatre

4BR Old Town Chicago Loft | Walk to Wells St From US $1,077
         

10.0 (120 Reviews)
Apartment
4BR Old Town Chicago Loft | Walk to Wells St
  • 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 $174
         

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10.0 (508 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 $300
         

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 $260
         

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9.8 (202 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 $546
         

10.0 (409 Reviews)
Apartment
52nd Floor MagMile Penthouse Views Fireplace Pool
  • Air Conditioner
  • Parking
  • Pool

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Mccomick Place/China town getaway From US $338
         

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New
Apartment
Mccomick Place/China town getaway
  • Parking
  • Pet Friendly
  • Child Friendly

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Villa D' Citta From US $269
         

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9.4 (118 Reviews)
Bed & Breakfast
Villa D' Citta
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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51st Floor MagMile Penthouse Views Balcony Pool From US $494
         

10.0 (228 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 $335
         

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 $355
         

10.0 (341 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 $1,464
         

10.0 (309 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 $312
         

10.0 (288 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 $675
         

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 $1,215
         

10.0 (213 Reviews)
Apartment
2-Story Penthouse Views, Fireplace, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

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2-Story Penthouse -Views, Fireplace, Pool, Gym From US $1,233
         

10.0 (201 Reviews)
Apartment
2-Story Penthouse -Views, Fireplace, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

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Magic Factory Loft 2West From US $647
         

10.0 (199 Reviews)
Apartment
Magic Factory Loft 2West
  • Air Conditioner
  • Parking
  • TV

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1F Chicago's Little italy Graystone nearDowntown From US $380
         

10.0 (179 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 $1,196
         

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 $1,194
         

10.0 (96 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 $1,376
         

10.0 (75 Reviews)
Apartment
Large 4BR/3BA Safe Old Town Location Walk Everywhere
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Historic Coach House Wicker Park From US $426
         

10.0 (70 Reviews)
House
Private Historic Coach House Wicker Park
  • Air Conditioner
  • Parking
  • TV

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52nd Floor Penthouse with Skyline Views and Pool From US $513
         

10.0 (65 Reviews)
Apartment
52nd Floor Penthouse with Skyline Views and Pool
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises 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 Chicago Theatre.

Weather in Chicago Theatre

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

December - February
High 52°F       Low 19°F
March - May
High 73°F       Low 33°F
June - August
High 86°F       Low 57°F
September - November
High 81°F       Low 31°F

Top Attractions Around Chicago Theatre, IL

Selloffcruises offers a large selection of top attractions around Chicago Theatre. Research things to do on your vacation before you visit Chicago Theatre.


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 Riverwalk Field Museum of Natural History University of Chicago Brookfield Zoo Northwestern University John Hancock Center Lincoln Park Zoo Water Tower Place

Chicago Theatre Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Chicago Theatre?

Currently, the total number of properties listed in 2026 is over 4285 in the Chicago Theatre area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chicago Theatre.