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Vacation Rentals in Chicago, IL

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All 203 Rentals in Chicago
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
Reviews (26) Make Inquiry
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
24 photos Details
Reviews (7) Make Inquiry
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3 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Reviews (7) Make Inquiry
Also consider
Charming, Peaceful, Vintage Apt on Lake Michigan
1 Bedroom, sleeps 4
$99 - $140 / night
Buckingham 3 Bedroom Townhome
3 Bedrooms, sleeps 8
$300 / night
Modern Wrigleyville 2 Bedroom Close To Red Line
2 Bedrooms, sleeps 6
$350 / night
PRIVATE 2-in-1 Bedroom(s)! Free Shuttle & Museums!
2 Bedrooms, sleeps 10
$99 / night
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The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
40 photos Details
Reviews (5) Make Inquiry
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1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (7) Make Inquiry
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
12 photos Details
Reviews (1) Make Inquiry
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3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (17) Make Inquiry
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The Loop
Studio, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Inquiry
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2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Inquiry
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3 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details
Reviews (32) Make Inquiry
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Inquiry
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Reviews (2) Make Inquiry
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3 Bedrooms, 1 Bathroom, Sleeps 5
22 photos Details
Reviews (11) Make Inquiry
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (1) Make Inquiry
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (7) Make Inquiry
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Near North Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
7 photos Details
Reviews (2) Make Inquiry
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Roscoe Village
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Reviews (3) Make Inquiry
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DePaul
4 Bedrooms, 1 Bathroom, Sleeps 9
Bookings
17 photos Details
Reviews (5) Make Inquiry
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
37 photos Details
Reviews (5) Make Inquiry
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West Town
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (7) Make Inquiry
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Inquiry
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Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
13 photos Details
Reviews (9) Make Inquiry
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Near North Side
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
Reviews (2) Make Inquiry
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Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (47) Make Inquiry
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
16 photos Details
Reviews (1) Make Inquiry
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Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
48 photos Details
Reviews (13) Make Inquiry
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Roscoe Village
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (2) Make Inquiry
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DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
14 photos Details
Reviews (1) Make Inquiry
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Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
12 photos Details
Reviews (5) Make Inquiry
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The Loop
Studio, 1 Bathroom, Sleeps 3
Bookings
13 photos Details
Reviews (2) Make Inquiry
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
6 photos Details
Reviews (2) Make Inquiry
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
26 photos Details
Reviews (4) Make Inquiry
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Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details
Reviews (11) Make Inquiry
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Bookings
22 photos Details
Reviews (4) Make Inquiry
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
14 photos Details
Reviews (7) Make Inquiry
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (1) Make Inquiry
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
7 photos Details
Reviews (1) Make Inquiry
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Inquiry
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West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
14 photos Details
Reviews (2) Make Inquiry
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
6 photos Details
Reviews (2) Make Inquiry
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  • Lakeview (20)
  • Lincoln Park (2)
  • Lincoln Square (1)
  • Near North Side (59)
  • Near South Side (0)
  • Northwest Side (18)
  • O'Hare (0)
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  • Rogers Park (5)
  • Roscoe Village (7)
  • Southwest Side (2)
  • The Loop (37)
  • University Village / Little Italy (0)
  • West Town (5)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (64)
  • Elder access (104)
  • Suitable for children (116)
  • Pet friendly (54)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (136)
  • Internet (128)
  • Other outdoor space (99)
  • Washer/Dryer (75)
  • Parking (61)
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Book Online(149)

Neighborhood

  • All (203)
  • DePaul (8)
  • East Side (0)
  • Gold Coast (15)
  • Hyde Park (0)
  • Lakeview (20)
  • Lincoln Park (2)
  • Lincoln Square (1)
  • Near North Side (59)
  • Near South Side (0)
  • Northwest Side (18)
  • O'Hare (0)
  • Pilsen (1)
  • Rogers Park (5)
  • Roscoe Village (7)
  • Southwest Side (2)
  • The Loop (37)
  • University Village / Little Italy (0)
  • West Town (5)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (64)
  • Elder access (104)
  • Suitable for children (116)
  • Pet friendly (54)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (136)
  • Internet (128)
  • Other outdoor space (99)
  • Washer/Dryer (75)
  • Parking (61)
  • View all amenities