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Search results; Over 1,000 homes in Chicago

Photo 1 of 29
Top guest favourite
Apartment in Chicago
Entire condo steps from lake, dining + shopping
3 bedrooms, 4 beds, 1 private bathroom
2–7 Nov
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5.0 out of 5 average rating, 60 reviews
Photo 1 of 29
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, 34 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
Photo 1 of 28
Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 529 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
12–17 Oct
4.91 out of 5 average rating, 542 reviews
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
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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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Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
26–31 Oct
4.99 out of 5 average rating, 364 reviews
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Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
26–31 Oct
4.98 out of 5 average rating, 128 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
16–21 Nov
4.95 out of 5 average rating, 175 reviews
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds
20–25 Oct
New place to stay
Photo 1 of 29
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Photo 1 of 29
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
1–6 Feb
5.0 out of 5 average rating, 42 reviews
Photo 1 of 29
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 101 reviews
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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
Photo 1 of 29
Top guest favourite
Guest suite in Chicago
Private Suite w/ offstreet pkg, at Logan Sq Blu Ln
1 bedroom, 2 beds
25–30 Oct
4.96 out of 5 average rating, 364 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds
1–6 Nov
New place to stay
Photo 1 of 29
Top guest favourite
Apartment in Chicago
Lincoln Square Gem!
2 bedrooms, 2 queen beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 509 reviews