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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Stylish Studio in Historic Logan Square
1 bedroom, 1 bed, 1 private bathroom
21–26 Oct
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4.97 out of 5 average rating, 356 reviews
Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
1–6 Nov
New place to stay
Top guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
19–24 Oct
4.98 out of 5 average rating, 189 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 60 reviews
Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 reviews
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
19–24 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 41 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 75 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
11–16 Jan
4.95 out of 5 average rating, 132 reviews
Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 527 reviews
Guest favourite
Flat in Chicago
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds
4–9 Oct
4.9 out of 5 average rating, 302 reviews
Top guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds
3–8 Nov
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
28 Oct – 2 Nov
4.95 out of 5 average rating, 273 reviews