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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 private bathrooms
19–24 Oct
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4.97 out of 5 average rating, 68 reviews
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Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 61 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
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
21–26 Sept
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 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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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Home in Wood Dale
Entire 3B/2B Home in Wood Dale-Near O'Hare Airport
3 bedrooms, 3 beds
4–9 Oct
New place to stay
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 110 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 175 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 3 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds
1–6 Nov
New place to stay
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Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
26–31 Oct
4.98 out of 5 average rating, 129 reviews
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Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 103 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
13–18 Dec
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds
22–27 Nov
4.94 out of 5 average rating, 476 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, 447 reviews