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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
Division St Designer Home In Heart of Wicker Park
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 294 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
15–20 Nov
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
26–31 Jul
4.95 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 67 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 125 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 83 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Home in Chicago
Elegant HP Row House | Gourmet Kitchen & Deck
3 bedrooms, 4 beds
20–25 Jul
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
15–20 Aug
New place to stay
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 34 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
20–25 Sept
4.95 out of 5 average rating, 19 reviews
Superhost
Flat in Chicago
Renovated 2BR in Prime L. | Sleeps 6 |Pet Friendly
2 bedrooms, 3 beds
2–7 Aug
New place to stay
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
14–19 Sept
4.97 out of 5 average rating, 67 reviews