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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
La Casita Norte
1 bedroom, 2 beds, 1 private bathroom
24–29 Oct
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4.94 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
8–13 Nov
4.9 out of 5 average rating, 126 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
8–13 Nov
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 76 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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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 Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 530 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 135 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, 4 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
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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Top guest favourite
Flat in Chicago
Charming, Spacious 3BR Lakeview Apt Near Transit
3 bedrooms, 3 beds
8–13 Nov
4.97 out of 5 average rating, 460 reviews
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Top guest favourite
Flat in Oak Park
Oak Park Space+Style Duplex Parking+Walk to Train
3 bedrooms, 5 beds
3–8 Dec
5.0 out of 5 average rating, 104 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
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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Guest favourite
Guest house in Oak Park
Entire Apartment in Oak Park, IL
3 bedrooms, 4 beds
25–30 Oct
4.84 out of 5 average rating, 100 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews