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Search results; Over 1,000 homes in Chicago

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Guest favourite
Apartment in Chicago
MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Oct
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4.89 out of 5 average rating, 194 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 111 reviews
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Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
13–18 Dec
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest suite in Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed
15–20 Nov
4.96 out of 5 average rating, 417 reviews
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
7–12 Jan
4.99 out of 5 average rating, 118 reviews
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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed
2–7 Nov
4.94 out of 5 average rating, 177 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 363 reviews
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Home in Wood Dale
Entire 3B/2B Home in Wood Dale-Near O'Hare Airport
3 bedrooms, 3 beds
4–9 Oct
New place to stay
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Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds
2–7 Nov
4.94 out of 5 average rating, 500 reviews
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Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed
9–14 Nov
4.92 out of 5 average rating, 544 reviews
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Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds
13–18 Dec
4.96 out of 5 average rating, 608 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Chicago
Chic 2BR Gem with Fireplace
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 165 reviews
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Guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
21–26 Nov
4.95 out of 5 average rating, 318 reviews
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Top guest favourite
Flat in Chicago
Your Logan Square Oasis with Lush Outdoor Haven!
2 bedrooms, 2 king beds
1–6 Nov
5.0 out of 5 average rating, 38 reviews