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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Beautiful Hollywood-Ridge Suite in Edgewater
1 bedroom, 1 bed, 1 private bathroom
6–11 Nov
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4.97 out of 5 average rating, 235 reviews
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Featured hotel
Hotel in Chicago
Sports Illustrated Resorts Chicago, Studio king
1 bedroom, 1 king bed, 1 bathroom
12–17 Oct
New place to stay
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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, 37 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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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, 136 reviews
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Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Oct
New place to stay
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
2–7 Jan
4.94 out of 5 average rating, 263 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, 4 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 Oak Park
Oak Park Space+Style Duplex Parking+Walk to Train
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 104 reviews
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Top guest favourite
Flat in Oak Park
Treetop Oasis Spacious & Modern King Bed + Parking
2 bedrooms, 4 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 102 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
22–27 Oct
4.91 out of 5 average rating, 543 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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Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
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Top guest favourite
Flat in Chicago
Charming, Spacious 3BR Lakeview Apt Near Transit
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 462 reviews
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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
4.97 out of 5 average rating, 172 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, 1 bathroom
23–28 Oct
4.88 out of 5 average rating, 450 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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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