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Search results; Over 1,000 homes in Chicago

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Featured hotel
Hotel in Chicago
Sports Illustrated Resorts Chicago, Studio king
1 bedroom, 1 king bed
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
8–13 Nov
5.0 out of 5 average rating, 37 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, 136 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
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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Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
16–21 Oct
New place to stay
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Top guest favourite
Flat in Oak Park
Oak Park Space+Style Duplex Parking+Walk to Train
3 bedrooms, 6 beds
1–6 Oct
5.0 out of 5 average rating, 104 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, 4 reviews
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
2–7 Jan
4.94 out of 5 average rating, 263 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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Top guest favourite
Flat in Oak Park
Treetop Oasis Spacious & Modern King Bed + Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 102 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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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, 462 reviews
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Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
4–9 Oct
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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
22–27 Oct
4.91 out of 5 average rating, 543 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, 171 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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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 4 reviews