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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
1 bedroom, 2 beds, 1 private bathroom
4–9 Jul
,
4.97 out of 5 average rating, 331 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms8 beds, 3 bathrooms,
23–28 Aug
4.91 out of 5 average rating, 117 reviews
Home in Chicago
Newly Renovated Home 4BD/3BTH with garage!
4 bedrooms5 beds, 3 bathrooms,
28 Jun – 3 Jul
New place to stay
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms3 beds, 1 bathroom,
28 Jun – 3 Jul
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms3 beds, 1.5 bathrooms,
12–17 Oct
4.95 out of 5 average rating, 112 reviews
Top guest favourite
Place to stay in Berwyn
room in family home
1 bedroom1 bed, 1 bathroom,
1–6 Dec
5.0 out of 5 average rating, 9 reviews
Home in Chicago
5BR Logan Sq | Sleeps 10 | Outdoor, Parking, Games
5 bedrooms5 queen beds, 2 bathrooms,
7–12 Jun
New place to stay
Top guest favourite
Place to stay in Chicago
Private, dog-friendly room near downtown Chicago
1 bedroom1 sofa bed, 1 bathroom,
29 Jun – 4 Jul
5.0 out of 5 average rating, 23 reviews
Home in Chicago
Steps to Lake & Beach! Multi-Level Oakland Haven
4 bedrooms5 beds, 4.5 bathrooms,
29 Jun – 4 Jul
New place to stay
Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms2 queen beds, 1 bathroom,
15–20 Nov
4.99 out of 5 average rating, 937 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms3 beds, 1 bathroom,
5–10 Jul
4.99 out of 5 average rating, 342 reviews
Top guest favourite
Home in Oak Park
Grove Flat
2 bedrooms2 beds, 1 bathroom,
15–20 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom1 king bed, 1 bathroom,
20–25 Oct
5.0 out of 5 average rating, 46 reviews
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
1 bedroom1 bed, 2 bathrooms,
17–22 Jun
New place to stay
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms4 beds, 2 bathrooms,
29 Aug – 3 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Chicago
The Logan Greystone
3 bedrooms3 beds, 1 bathroom,
30 Aug – 4 Sept
4.98 out of 5 average rating, 60 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms2 beds, 2 bathrooms,
9–14 Aug
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms2 queen beds, 1 bathroom,
18–23 Jul
4.97 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Chicago
Coach House in Historic Old Town Chicago
1 bedroom2 beds, 1 bathroom,
14–19 Jun
4.96 out of 5 average rating, 126 reviews