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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Travelers Retreat in Old Town Chicago
1 bedroom, 2 beds, 1 private bathroom
22–27 Aug
,
4.99 out of 5 average rating, 141 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 125 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago
Modern 1-Bedroom w/ off-street parking space
4.93 out of 5 average rating, 136 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
4.99 out of 5 average rating, 96 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
Top guest favourite
Room in Chicago
Fresh and Sunny Bed & Bath by UofC
4.91 out of 5 average rating, 255 reviews, 1 queen bed, 1 bathroom
14–19 Aug
Guest favourite
Flat in Chicago
Modern Chicago 1BR | Near Lincoln Park & Loop
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Aug
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
9–14 Nov
Room in Chicago
New Quiet Clean Room 1 guest
1 double bed, 1 bathroom
25–30 Jul
Guest favourite
Flat in Oak Park
Bright Boho Haven free parking
4.86 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Sept
Top guest favourite
Guest suite in Chicago
Studio 15 Minutes From Ohare!
4.97 out of 5 average rating, 202 reviews, 1 bed, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Flat in Chicago
Next to Riot Fest, spacious garden apartment
4.92 out of 5 average rating, 218 reviews, 1 bedroom, 3 beds, 1 bathroom
31 Mar – 5 Apr
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
4.98 out of 5 average rating, 410 reviews, 2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
4.98 out of 5 average rating, 190 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Oct
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 143 reviews, 1 single bed, 1 bathroom
18–23 Aug
Guest favourite
Room in Oak Park
Walk to Train | Master Suite A Queen Bed Sleeps 2
4.97 out of 5 average rating, 39 reviews, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Room in Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
4.92 out of 5 average rating, 111 reviews, 1 single bed, 1 bathroom
19–24 Aug
Guest favourite
Room in Bridgeview
Comfortable Private Room with Easy Chicago Access
5.0 out of 5 average rating, 14 reviews, 1 queen bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest house in Chicago
Guesthouse | Near public transit and Lake front
4.91 out of 5 average rating, 123 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Sept
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 303 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug