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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
A space crafted for comfort and intentional stays.
1 bedroom, 1 bed, 1 private bathroom
4–9 Aug
,
4.95 out of 5 average rating, 220 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 96 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 122 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
6 bedrooms, 11 beds, 3 bathrooms
26–31 Jul
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 435 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Place to stay in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
4.89 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Chicago
The Nest | Luxe Garden Unit Near Downtown
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
5.0 out of 5 average rating, 7 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
4.99 out of 5 average rating, 103 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Flat in Chicago
Apartment near McCormick w/ gym & workspace
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug