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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Superhost
Flat in Chicago
The Lakefront Lookout (Rooftop Deck • Gym)
2 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
,
4.81 out of 5 average rating, 232 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
Newly renovated near Millennium Park
1 bedroom, 1 queen bed, 1 bathroom
22–27 Jul
4.97 out of 5 average rating, 93 reviews
Home in Franklin Park
Full, fun cozy house!
2 bedrooms, 4 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 5 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds, 2 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Home in Brookfield
Sunlit mid-century brick ranch, tree-lined street
4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Chicago
Minimal duplex with free private parking
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Guest favourite
Home in Chicago
Historic bungalow with free parking near Hyde Park
2 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
6 bedrooms, 11 beds, 3 bathrooms
26–31 Jul
Place to stay in Chicago
Central spot near downtown with workspace
1 bedroom, 1 queen bed, 2 bathrooms
13–18 Aug
New place to stay
Guest favourite
Place to stay in Chicago
En suite near UChicago, 3-min to CTA
1 bedroom, 1 king bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Room in Chicago
Near UofC with patio and free parking
1 double bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 182 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
1 bedroom, 1 bed, 2 bathrooms
4–9 Aug
New place to stay
Top guest favourite
Flat in Chicago
Sun-filled top floor near 606 trail
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.77 out of 5 average rating, 569 reviews
Top guest favourite
Flat in Chicago
Massive roof deck in Bronzeville
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Flat in Chicago
Apartment near McCormick w/ gym & workspace
1 bedroom, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 6 reviews