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Search resultsOver 1,000 homes

Condo in Little Italy
Private hot tub - King bed suite - Free parking
2 beds
May 7 – 12
$183 per night
Superhost
Apartment in Little Italy
UIC / Little Italy - Charming 1 Bed 1 Bath Apt.
2 beds
Jun 30 – Jul 6
$199 per night
Superhost
Private room in Little Italy
Incredible Little Italy location!
1 king bed
Aug 18 – 24
$63 per night
Apartment in Little Italy
UIC / Little Italy - Lovely 1 Bed 1 Bath Apt.
2 beds
May 14 – 19
$104 per night
Apartment in Little Italy
Modern Chic Apt Close to Downtown Chicago FREE PKG
4 double beds
Apr 8 – 13
$268 per night
Superhost
Apartment in Little Italy
UIC / Little Italy - Unique & Private 1 Bedroom
2 beds
Apr 1 – 6
$154 per night
Superhost
Private room in Little Italy
Private room(s) at a great home in Little Italy .
1 queen bed
May 20 – 26
$99 per night
Superhost
Guesthouse in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 queen beds
May 28 – Jun 2
$173 per night
Plus
Private room in Pilsen Historic District
Private room/south loop*
1 bed
Apr 1 – 6
$40 per night, originally $50
Apartment in West Loop
Sonder Market Hall | Studio Apartment w/ City View
Apr 1 – 6
$119 per night
Apartment in Little Italy
UIC / Little Italy - Adorable 2 Bed 1 Bath Apt.
2 beds
May 14 – 19
$117 per night
Home in Little Italy
Great City Views + Free Parking
3 queen beds
Apr 1 – 6
$161 per night
Private room in Little Italy
Private room in apartment in Fantastic location
1 queen bed
Apr 2 – 8
$60 per night
Private room in Little Italy
ChicagoRiver Double Room (+Complimentary BIKES)
1 double bed
Apr 22 – 27
$66 per night
Superhost
Private room in Humboldt Park
Chic PRVT Room w/ Full Bathroom | Logan Square
1 double bed
Apr 9 – 14
$36 per night
Superhost
Apartment in Pilsen Historic District
Perfect for a Hip and Romantic Getaway
1 bed
Apr 1 – 6
$97 per night
Superhost
Apartment in West Loop
2BR/2BA Furnished Apartment in Chicago
2 queen beds
Apr 9 – 14
$95 per night
Private room in Englewood
Amazing 1 bed room near downtown Unit 2 room #2
1 bed
Apr 1 – 6
$28 per night
Superhost