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Holiday Rentals in Chicago, IL

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All 179 Rentals in Chicago
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From
$184
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$441
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
From
$166
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details
Reviews (32) Make Enquiry
Also consider
Historic, Chicago
1 Bedroom, sleeps 2
$188 - $222 / night
Big studio with a queen bed. New build August 2013
1 Bedroom, sleeps 2
$72 - $88 / night
Sunny Urban Outpost in Logan Square
2 Bedrooms, sleeps 4
$134 / night
Beautiful 2 bed room apartment
2 Bedrooms, sleeps 4
$88 - $110 / night
From
$335
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Enquiry
From
$400
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
15 photos Details
Reviews (15) Make Enquiry
From
$229
Per Night
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (1) Make Enquiry
From
$558
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
24 photos Details
Reviews (7) Make Enquiry
From
$195
Per Night
Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
48 photos Details
Reviews (13) Make Enquiry
Get the List
From
$195
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 5
22 photos Details
Reviews (11) Make Enquiry
From
$279
Per Night
Roscoe Village
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (2) Make Enquiry
From
$362
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
23 photos Details
Reviews (12) Make Enquiry
From
$335
Per Night
Roscoe Village
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Reviews (3) Make Enquiry
From
$613
Per Night
Near North Side
2 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
13 photos Details
Reviews (3) Make Enquiry
From
$296
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
9 photos Details
Reviews (1) Make Enquiry
From
$558
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
26 photos Details
Reviews (16) Make Enquiry
From
$390
Per Night
Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (47) Make Enquiry
From
$178
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Enquiry
From
$201
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (18) Make Enquiry
From
$95
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details
Reviews (26) Make Enquiry
From
$149
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (7) Make Enquiry
From
$217
Per Night
Rogers Park
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (4) Make Enquiry
From
$167
Per Night
DePaul
4 Bedrooms, 1 Bathroom, Sleeps 9
Bookings
17 photos Details
Reviews (5) Make Enquiry
From
$697
Per Night
Near North Side
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
Reviews (2) Make Enquiry
From
$167
Per Night
DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
14 photos Details
Reviews (1) Make Enquiry
From
$335
Per Night
Near North Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
7 photos Details
Reviews (2) Make Enquiry
From
$167
Per Night
The Loop
Studio, 1 Bathroom, Sleeps 3
Bookings
13 photos Details
Reviews (2) Make Enquiry
From
$89
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$112
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Bookings
22 photos Details
Reviews (4) Make Enquiry
From
$220
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
7 photos Details
Reviews (1) Make Enquiry
From
$99
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (1) Make Enquiry
From
$279
Per Night
Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
20 photos Details
Reviews (11) Make Enquiry
From
$100
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
6 photos Details
Reviews (2) Make Enquiry
From
$279
Per Night
West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
14 photos Details
Reviews (2) Make Enquiry
From
$195
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
19 photos Details
Reviews (3) Make Enquiry
From
$195
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
Bookings
13 photos Details
Reviews (1) Make Enquiry
From
$117
Per Night
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Reviews (7) Make Enquiry
From
$340
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
12 photos Details
Reviews (6) Make Enquiry
From
$167
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
Bookings
15 photos Details
Reviews (2) Make Enquiry
From
$128
Per Night
Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
23 photos Details
Reviews (3) Make Enquiry
From
$84
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
10 photos Details
Reviews (2) Make Enquiry
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Neighbourhood

  • All (179)
  • DePaul (10)
  • East Side (0)
  • Gold Coast (11)
  • Hyde Park (0)
  • Lakeview (21)
  • Lincoln Park (1)
  • Lincoln Square (1)
  • Near North Side (45)
  • Near South Side (0)
  • Northwest Side (22)
  • O'Hare (0)
  • Pilsen (1)
  • Rogers Park (6)
  • Roscoe Village (8)
  • Southwest Side (2)
  • The Loop (26)
  • University Village / Little Italy (0)
  • West Town (3)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighbourhoods

Suitability

  • Wheelchair access (43)
  • Elder access (81)
  • Suitable for children (95)
  • Pet friendly (35)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (127)
  • Internet (122)
  • Other outdoor space (91)
  • Washer/Dryer (81)
  • Parking (58)
  • View all amenities