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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Stone Mansion Sleeps 10-20 Free parking & TV
4 bedrooms, 9 beds, 2 private bathrooms
15–20 Nov
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4.92 out of 5 average rating, 290 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 12 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
1–6 Oct
4.91 out of 5 average rating, 82 reviews
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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
25–30 Oct
5.0 out of 5 average rating, 7 reviews
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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, 35 reviews
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Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 65 reviews
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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
19–24 Oct
4.96 out of 5 average rating, 93 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
8–13 Nov
4.95 out of 5 average rating, 111 reviews
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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, 529 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
1–6 Nov
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
23–28 Oct
4.88 out of 5 average rating, 450 reviews
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Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
15–20 Nov
4.99 out of 5 average rating, 363 reviews
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Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
18–23 Oct
4.93 out of 5 average rating, 249 reviews
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds
1–6 Oct
New place to stay
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Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
20–25 Oct
4.91 out of 5 average rating, 278 reviews