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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Modern vintage chic steps from Wrigley: park free
3 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 271 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 96 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 123 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds, 2 bathrooms
15–20 Aug
New place to stay
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
9–14 Aug
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
4 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 83 reviews
Top guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds, 1 bathroom
13–18 Oct
4.98 out of 5 average rating, 105 reviews
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Chicago
Amazing Fun Condo, City view next to 606 Trail!
2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 88 reviews