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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
2 King Beds /Easy Downtown / Free Str Parking-Read
2 bedrooms, 4 beds, 1 private bathroom
9–14 Sept
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4.88 out of 5 average rating, 284 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Guest favourite
Room in Chicago
Lovely Front Room #1 in a New Renovated Apartment
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 349 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 568 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Guest suite in Chicago
Private Lincoln Square Garden Apt
4.92 out of 5 average rating, 490 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Nov
Top guest favourite
Apartment in Chicago
Bright, new 2BR in the heart of East Lakeview
4.99 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Chicago
2br/2ba, A+ location by Mag mile, views & spacious
4.93 out of 5 average rating, 369 reviews, 2 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Chicago
Rogers Park Penthouse
4.97 out of 5 average rating, 103 reviews, 1 bed, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Forest Park
Like a Treehouse!
5.0 out of 5 average rating, 374 reviews, 1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
4.98 out of 5 average rating, 157 reviews, 1 bedroom, 3 beds, 1 bathroom
17–22 Aug
Top guest favourite
Flat in Chicago
Beautiful, sunny 2nd floor 3BR/1BA w free parking
4.93 out of 5 average rating, 164 reviews, 3 bedrooms, 4 beds, 1 bathroom
24–29 Oct