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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
4–9 Oct
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4.97 out of 5 average rating, 150 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
30 Oct – 4 Nov
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
15–20 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
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, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 7 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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Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
8–13 Nov
4.95 out of 5 average rating, 111 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
25–30 Oct
5.0 out of 5 average rating, 3 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 bathroom
1–6 Oct
4.91 out of 5 average rating, 82 reviews
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Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.93 out of 5 average rating, 249 reviews
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Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 34 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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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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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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Top guest favourite
Flat in Oak Park
Oak Park Space+Style Duplex Parking+Walk to Train
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 103 reviews
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Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed, 1 bathroom
20–25 Oct
4.91 out of 5 average rating, 278 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, 64 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, 92 reviews