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Search results; Over 1,000 homes in Chicago

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Hotel in Chicago
Modern design with VU Skyward rooftop bar
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.73 out of 5 average rating, 273 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Jan
4.75 out of 5 average rating, 4 reviews
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 3 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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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorites xx
5 bedrooms, 8 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 151 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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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 4 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
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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Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Flat in Chicago
Relaxing 2BR Stay | Comfy Queen Bed + Fast WiFi
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.83 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 111 reviews
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Guest favourite
Home in Chicago
Lux Chicago SFH 6 Br house w/ Garage + Yard
6 bedrooms, 7 beds, 3.5 bathrooms
13–18 Oct
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Guest house in Oak Park
Entire Apartment in Oak Park, IL
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.84 out of 5 average rating, 100 reviews
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Top guest favourite
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
16–21 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.8 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Nov
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 5 reviews