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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in West Loop
Clean & Best Location 2BR+2BA | Mapletree Suites
2 bedrooms, 3 beds, 2 private bathrooms
24–29 Jul
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4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Humboldt Park
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
Flat in Logan Square
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
9–14 Aug
Guest favourite
Room in Irving Park
Lovely Front Room 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
Room in West Side
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 521 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Superhost
Place to stay in South Side
Woodlawn Beauty: Room 2
4.5 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 348 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Apartment in Lake View
Bright, new 2BR in the heart of East Lakeview
4.99 out of 5 average rating, 128 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Chicago Loop
Upscale High-Rise Apt · Rooftop Pool + Views
4.97 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
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
Place to stay in Chicago
Guest room in Dunning, Chicago IL
New place to stay, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Guest favourite
Apartment in North Side
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