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Pet Friendly Holiday Rentals in Chicago

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From
$214
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
19 photos Details
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From
$267
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
39 photos Details
Reviews (1) Make Enquiry
From
$321
Per Night
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
26 photos Details
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From
$321
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
19 photos Details
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From
$149
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
14 photos Details
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From
$159
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
10 photos Details
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From
$321
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details
Reviews (6) Make Enquiry
From
$70
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
14 photos Details
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Get the List
From
$91
Per Night
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
15 photos Details
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From
$2,855
Per Month
The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
40 photos Details
Reviews (5) Make Enquiry
From
$209
Per Night
Rogers Park
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
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From
$144
Per Night
Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
28 photos Details
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From
$170
Per Night
Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
30 photos Details
Reviews (5) Make Enquiry
From
$422
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
From
$176
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
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From
$160
Per Night
DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
14 photos Details
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From
$214
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
11 photos Details
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From
$134
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
16 photos Details
Reviews (1) Make Enquiry
From
$95
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (1) Make Enquiry
From
$213
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Enquiry
From
$267
Per Night
West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
14 photos Details
Reviews (2) Make Enquiry
From
$107
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 3
9 photos Details
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From
$315
Per Night
Lincoln Square
4 Bedrooms, 4 Bathrooms, Sleeps 8
17 photos Details
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From
$428
Per Night
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
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From
$267
Per Night
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
33 photos Details
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From
$214
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
4 photos Details
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From
$170
Per Night
Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
8 photos Details
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From
$267
Per Night
West Town
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
12 photos Details
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From
$321
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
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From
$642
Per Night
Lakeview
5 Bedrooms, 2 Bathrooms, Sleeps 16
24 photos Details
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From
$1,067
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
$267
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
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From
$267
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
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From
$374
Per Night
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
27 photos Details
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From
$454
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details
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From
$320
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
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From
$320
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Bookings
39 photos Details
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From
$241
Per Night
1 Bedroom, 1 Bathroom, Sleeps 5
20 photos Details
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From
$214
Per Night
West Town
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
10 photos Details
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From
$267
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Bookings
28 photos Details
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From
$213
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
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From
$321
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
31 photos Details
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From
$294
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$209
Per Night
The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
23 photos Details
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From
$428
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 5
32 photos Details
Make Enquiry
From
$321
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
28 photos Details
Make Enquiry
From
$213
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
9 photos Details
Make Enquiry
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Neighbourhood

  • All (53)
  • DePaul (4)
  • East Side (0)
  • Gold Coast (2)
  • Hyde Park (0)
  • Lakeview (1)
  • Lincoln Park (0)
  • Lincoln Square (1)
  • Near North Side (19)
  • Near South Side (0)
  • Northwest Side (4)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (4)
  • Roscoe Village (0)
  • Southwest Side (0)
  • The Loop (12)
  • University Village / Little Italy (0)
  • West Town (3)
  • Wicker Park / Bucktown (0)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (29)
  • Elder access (34)
  • Suitable for children (47)
  • Pet friendly (53)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (33)
  • Internet (32)
  • Other outdoor space (28)
  • Washer/Dryer (23)
  • Parking (20)
  • View all amenities