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Search results; Over 1,000 homes in Chicago

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Townhouse in Chicago
Vital Urban: Spa Inspired Retreat
2 bedrooms, 3 beds, 2.5 private bathrooms
23–28 Oct
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4.75 out of 5 average rating, 36 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
8–13 Nov
4.9 out of 5 average rating, 126 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
4.96 out of 5 average rating, 93 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 135 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Jan
4.75 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
7–12 Nov
4.9 out of 5 average rating, 530 reviews
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Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 65 reviews
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Guest favourite
Rooms in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 26 reviews
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Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in Oak Park
Oak Park Space+Style Duplex Parking+Walk to Train
3 bedrooms, 6 beds, 2.5 bathrooms
3–8 Dec
5.0 out of 5 average rating, 104 reviews
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Room in Chicago
Brown Stone Walkup in the Best Location Chill/Safe
1 bed, 1 bathroom
13–18 Oct
New place to stay
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 171 reviews
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Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
13–18 Oct
4.91 out of 5 average rating, 82 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 363 reviews
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Top guest favourite
Flat in Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds, 6 bathrooms
8–13 Nov
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 263 reviews