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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
28 Sept – 3 Oct
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5.0 out of 5 average rating, 68 reviews
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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 46 reviews
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Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
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Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 28 reviews
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Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
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Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
6–11 Sept
4.88 out of 5 average rating, 146 reviews
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Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
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Flat in Oak Park
Curated & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 97 reviews
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Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.88 out of 5 average rating, 78 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
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Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 61 reviews
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Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
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Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
8–13 Nov
4.99 out of 5 average rating, 361 reviews
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Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
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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