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Vacation Rentals in Chicago, IL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 194 Rentals in Chicago
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From
$260
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Near North Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
7 photos Details
Reviews (2) Make Inquiry
From
$195
Per Night
Rogers Park
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (4) Make Inquiry
Also consider
Penthouse At The Lex...massive Skyline Views!!
2 Bedrooms, sleeps 6
$300 / night
Music Suite - Quiet, Trendy Two Bedroom Apartment
2 Bedrooms, sleeps 5
$225 - $275 / night
Nice 1 BR in Lincoln Park, Chicago
1 Bedroom, sleeps 3
$74 - $140 / night
PRIVATE 2-in-1 Bedroom(s)! Free Shuttle & Museums!
2 Bedrooms, sleeps 10
$99 / night
From
$500
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (6) Make Inquiry
From
$359
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
15 photos Details
Reviews (15) Make Inquiry
From
$625
Per Night
Near North Side
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
Reviews (2) Make Inquiry
From
$395
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Inquiry
From
$135
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
37 photos Details
Reviews (4) Make Inquiry
Get the List
From
$265
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Roscoe Village
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Reviews (3) Make Inquiry
From
$350
Per Night
Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
Reviews (47) Make Inquiry
From
$175
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 5
22 photos Details
Reviews (11) Make Inquiry
From
$150
Per Night
DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
14 photos Details
Reviews (1) Make Inquiry
From
$550
Per Night
Near North Side
2 Bedrooms, 3 Bathrooms, Sleeps 8
13 photos Details
Reviews (3) Make Inquiry
From
$300
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Inquiry
From
$205
Per Night
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (1) Make Inquiry
From
$159
Per Night
Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 5
30 photos Details
Reviews (5) Make Inquiry
From
$125
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details
Reviews (1) Make Inquiry
From
$150
Per Night
DePaul
4 Bedrooms, 1 Bathroom, Sleeps 9
17 photos Details
Reviews (5) Make Inquiry
From
$205
Per Night
Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (9) Make Inquiry
From
$190
Per Night
Southwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 6
51 photos Details
Reviews (28) Make Inquiry
From
$120
Per Night
West Town
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (6) Make Inquiry
From
$190
Per Night
Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
48 photos Details
Reviews (13) Make Inquiry
From
$300
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Reviews (7) Make Inquiry
From
$250
Per Night
Roscoe Village
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (2) Make Inquiry
From
$165
Per Night
DePaul
2 Bedrooms, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (2) Make Inquiry
From
$150
Per Night
The Loop
Studio, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (1) Make Inquiry
From
$80
Per Night
Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
6 photos Details
Reviews (2) Make Inquiry
From
$250
Per Night
Northwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (11) Make Inquiry
From
$100
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
22 photos Details
Reviews (4) Make Inquiry
From
$89
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (1) Make Inquiry
From
$200
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
7 photos Details
Reviews (1) Make Inquiry
From
$85
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (23) Make Inquiry
From
$129
Per Night
Southwest Side
4 Bedrooms, 4 Bathrooms, Sleeps 10
9 photos Details
Reviews (6) Make Inquiry
From
$199
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
13 photos Details
Reviews (1) Make Inquiry
From
$139
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
14 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (3) Make Inquiry
From
$90
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
6 photos Details
Reviews (2) Make Inquiry
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Book Online(145)
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Neighborhood

  • All (194)
  • DePaul (8)
  • East Side (0)
  • Gold Coast (15)
  • Hyde Park (0)
  • Lakeview (19)
  • Lincoln Park (2)
  • Lincoln Square (0)
  • Near North Side (59)
  • Near South Side (0)
  • Northwest Side (18)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (4)
  • Roscoe Village (7)
  • Southwest Side (3)
  • The Loop (35)
  • University Village / Little Italy (0)
  • West Town (4)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (64)
  • Elder access (104)
  • Suitable for children (116)
  • Pet friendly (53)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (131)
  • Internet (123)
  • Other outdoor space (97)
  • Washer/Dryer (75)
  • Parking (68)
  • View all amenities
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Book Online(145)

Neighborhood

  • All (194)
  • DePaul (8)
  • East Side (0)
  • Gold Coast (15)
  • Hyde Park (0)
  • Lakeview (19)
  • Lincoln Park (2)
  • Lincoln Square (0)
  • Near North Side (59)
  • Near South Side (0)
  • Northwest Side (18)
  • O'Hare (0)
  • Pilsen (0)
  • Rogers Park (4)
  • Roscoe Village (7)
  • Southwest Side (3)
  • The Loop (35)
  • University Village / Little Italy (0)
  • West Town (4)
  • Wicker Park / Bucktown (3)
Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (64)
  • Elder access (104)
  • Suitable for children (116)
  • Pet friendly (53)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (131)
  • Internet (123)
  • Other outdoor space (97)
  • Washer/Dryer (75)
  • Parking (68)
  • View all amenities