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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds, 1 private bathroom
12–18 Oct
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4.94 out of 5 average rating, 249 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
27 Sept – 2 Oct
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
New place to stay
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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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
20–25 Sept
4.91 out of 5 average rating, 82 reviews
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Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 8 beds, 3.5 bathrooms
19–24 Sept
4.96 out of 5 average rating, 48 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Dec
New place to stay
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 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
Andersonville Living
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 499 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, 447 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, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 101 reviews
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Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 64 reviews
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Superhost
Home in Chicago
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Chicago
Warm and Welcoming 2BR Unit Walk to Dining and CTA
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
New place to stay