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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Guest suite in Chicago
Great location, private entry and patio!
1 bedroom, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.96 out of 5 average rating, 347 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
Top guest favourite
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
Peaceful garden unit with private entrance
3 bedrooms, 3 queen beds, 2 bathrooms
26–31 Jul
New place to stay
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Home in Chicago
1908 coach house with rooftop skyline views
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 19 reviews
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
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
Place to stay in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
New place to stay
Superhost
Home in Chicago
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
6 bedrooms, 11 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 13 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
Top guest favourite
Flat in Chicago
Eclectic decor in Pilsen’s art district
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 121 reviews
Place to stay in Chicago
Near McCormick Place and train station
1 bedroom, 1 bed, 2 bathrooms
4–9 Aug
New place to stay
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
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 157 reviews
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
Place to stay in Chicago
Halfway between O’Hare and downtown
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 3 reviews