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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds, 1 private bathroom
3–8 Nov
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4.96 out of 5 average rating, 144 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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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, 529 reviews
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Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 44 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Dec
New place to stay
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Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 61 reviews
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
New place to stay
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Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 128 reviews
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
New place to stay
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
4.95 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 499 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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Guest favourite
Apartment in Chicago
Lincoln Square Gem!
2 bedrooms, 2 queen beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 509 reviews
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Top guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.91 out of 5 average rating, 542 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Flat in Chicago
Modern 2 BR 1 Bathroom in Logan Square/Avondale
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay