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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Great location, private entry and patio!
1 bedroom, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.96 out of 5 average rating, 353 reviews
Superhost
Flat in Chicago
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds
16–21 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
12–17 Aug
4.91 out of 5 average rating, 118 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds
17–22 Aug
New place to stay
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
23–28 Aug
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Flat in Chicago
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds
10–15 Sept
New place to stay
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 356 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, 39 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Room in Chicago
Rogers Park Penthouse
1 bed
26–31 Oct
4.97 out of 5 average rating, 107 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
16–21 Aug
4.91 out of 5 average rating, 43 reviews