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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Guest suite in Chicago
2BR near McCormick, Obama Ctr, UChicago & Downtown
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
,
5.0 out of 5 average rating, 33 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 Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
New place to stay
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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, 47 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
4.98 out of 5 average rating, 170 reviews
Photo 1 of 29
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
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, 25 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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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, 34 reviews
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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 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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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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Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 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, 133 reviews
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Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 10 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