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  • Showing 1-50 of 300+
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Additional fees apply. Taxes may be added.
Excellent! 4.5/5
(67 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #690239vb
67
Viewed 140 times in the last 48 hours
Excellent! 4.7/5
(48 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #445608vb
48
Viewed 66 times in the last 48 hours
Wonderful! 4.8/5
(102 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
Apartment #578762vb
102
Viewed 64 times in the last 48 hours
Wonderful! 4.9/5
(73 reviews)
avg/night
  • 4 BR
  • 4 BA
  • Sleeps 12
Condo #679790vb
73
Viewed 100 times in the last 48 hours
Wonderful! 4.9/5
(32 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
Townhome #3917584
32
Viewed 42 times in the last 48 hours
Excellent! 4.4/5
(14 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Multiple rentals Apartment #4261388
14
Viewed 27 times in the last 48 hours
Wonderful! 4.9/5
(36 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #3790035
36
Viewed 81 times in the last 48 hours
Wonderful! 4.8/5
(53 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #290256vb
53
Viewed 95 times in the last 48 hours
Excellent! 4.7/5
(107 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Condo #222038
107
Viewed 83 times in the last 48 hours
Wonderful! 4.9/5
(55 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
Apartment #3768288
55
Viewed 46 times in the last 48 hours
Wonderful! 4.8/5
(27 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #3795191
27
Viewed 59 times in the last 48 hours
Wonderful! 4.8/5
(48 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #265424vb
48
Viewed 136 times in the last 48 hours
Wonderful! 4.9/5
(32 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #735859vb
32
Viewed 28 times in the last 48 hours
Excellent! 4.4/5
(14 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #836457vb
14
Viewed 29 times in the last 48 hours
Exceptional! 5/5
(32 reviews)
avg/night
  • 1 BR
  • 2 BA
  • Sleeps 2
Apartment #864022vb
32
Viewed 29 times in the last 48 hours
Excellent! 4.7/5
(41 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #3751630
41
Viewed 51 times in the last 48 hours
Excellent! 4.5/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #622632vb
31
Viewed 60 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #4172462
9
Viewed 26 times in the last 48 hours
Exceptional! 5/5
(64 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
Apartment #627209vb
64
Viewed 49 times in the last 48 hours
Excellent! 4.7/5
(22 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #4146480
22
Viewed 24 times in the last 48 hours
Wonderful! 4.9/5
(24 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #894129vb
24
Viewed 90 times in the last 48 hours
Excellent! 4.6/5
(44 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Apartment #3833362
44
Viewed 25 times in the last 48 hours
Wonderful! 4.9/5
(72 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358005
72
Viewed 42 times in the last 48 hours
Excellent! 4.7/5
(45 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
Apartment #3645846
45
Viewed 49 times in the last 48 hours
Wonderful! 4.8/5
(71 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 6
Apartment #301852vb
71
Viewed 22 times in the last 48 hours
Excellent! 4.6/5
(12 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #4172463
12
Viewed 53 times in the last 48 hours
Wonderful! 4.8/5
(55 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #296798
55
Viewed 35 times in the last 48 hours
Wonderful! 4.9/5
(18 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #695418vb
18
Viewed 20 times in the last 48 hours
Wonderful! 4.8/5
(25 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #870495vb
25
Viewed 38 times in the last 48 hours
Wonderful! 4.9/5
(52 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358013
52
Viewed 62 times in the last 48 hours
Excellent! 4.5/5
(82 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 10
Condo #400905vb
82
Viewed 50 times in the last 48 hours
Wonderful! 4.9/5
(62 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3720918
62
Viewed 57 times in the last 48 hours
Excellent! 4.7/5
(42 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 5
Apartment #600158vb
42
Viewed 16 times in the last 48 hours
Excellent! 4.3/5
(14 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #4280611
14
Viewed 22 times in the last 48 hours
Excellent! 4.5/5
(24 reviews)
avg/night
  • Studio
  • 1 BA
  • Sleeps 2
Apartment #742485vb
24
Viewed 28 times in the last 48 hours
Wonderful! 4.9/5
(47 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #939473
47
Viewed 41 times in the last 48 hours
Wonderful! 4.9/5
(14 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #780506vb
14
Viewed 27 times in the last 48 hours
Wonderful! 4.9/5
(17 reviews)
avg/night
  • Studio
  • 1 BA
  • Sleeps 2
Condo #844695vb
17
Viewed 24 times in the last 48 hours
Exceptional! 5/5
(26 reviews)
avg/night
  • 1 BR
  • Sleeps 4
Apartment #870614vb
26
Viewed 23 times in the last 48 hours
Very Good! 4.2/5
(21 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 5
Apartment #870916vb
21
Viewed 25 times in the last 48 hours
Wonderful! 4.9/5
(76 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Apartment #358020
76
Viewed 29 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3645759
7
Viewed 29 times in the last 48 hours
Exceptional! 5/5
(15 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #871091vb
15
Viewed 5 times in the last 48 hours
Wonderful! 4.9/5
(65 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #374687
65
Viewed 39 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 3
Apartment #895525vb
8
Viewed 45 times in the last 48 hours
Excellent! 4.6/5
(19 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #871119vb
19
Viewed 19 times in the last 48 hours
Wonderful! 4.9/5
(26 reviews)
avg/night
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 12
House #840552vb
26
Viewed 96 times in the last 48 hours
Wonderful! 4.9/5
(29 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Apartment #856957vb
29
Viewed 25 times in the last 48 hours
Exceptional! 5/5
(22 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #3627370
22
Viewed 34 times in the last 48 hours
Wonderful! 4.9/5
(12 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 6
Apartment #903748vb
12
Viewed 42 times in the last 48 hours
  • 1 - 50 of 300+

Vacation Rentals in Chicago, Illinois (300+)