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Search results; Over 1,000 homes in Chicago

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Guest favourite
Home in Chicago
H&H 1896 - Spacious, Fully Stocked, & Free Parking
6 bedrooms, 9 beds, 4 private bathrooms
20–25 Sept
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4.95 out of 5 average rating, 119 reviews
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Featured hotel
Hotel in Chicago
Deluxe double
1 bedroom, 2 double beds, 1 bathroom
24–29 Sept
4.92 out of 5 average rating, 62 reviews
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Featured hotel
Hotel in Chicago
Studio king
1 bedroom, 1 king bed, 1 bathroom
17–22 Sept
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, 34 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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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
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
4.95 out of 5 average rating, 175 reviews
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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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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
New place to stay
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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
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 128 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
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds, 1 bathroom
2–7 Oct
4.91 out of 5 average rating, 542 reviews
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Guest favourite
Flat in Chicago
Bright Apartment
1 bedroom, 2 beds, 1 bathroom
7–12 Dec
4.91 out of 5 average rating, 151 reviews
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Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Guest suite in Chicago
Logan Square Chicago 2BR cottage, close to it all!
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 130 reviews
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Featured hotel
Hotel in Rosemont
Accessible Deluxe King with Roll-In Shower
1 bedroom, 1 king bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews