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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
19–24 Jul
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4.97 out of 5 average rating, 135 reviews
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 246 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 433 reviews
Home in Chicago
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms, 10 beds, 3.5 bathrooms
27 Jun – 2 Jul
New place to stay
Top guest favourite
Flat in Chicago
Historic oasis in the middle of everything.
3 bedrooms, 4 beds, 1 bathroom
21–26 Jun
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Place to stay in Chicago
Twin Bed | Near Train Station | McCormick Pl
1 bedroom, 1 bed, 2 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Flat in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
1 bedroom, 3 queen beds, 1 bathroom
21–26 Jun
4.98 out of 5 average rating, 155 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, 108 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
1–6 Jul
4.94 out of 5 average rating, 139 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
14–19 Mar
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Place to stay in Berwyn
room in family home
1 bedroom, 1 bed, 1 bathroom
1–6 Dec
5.0 out of 5 average rating, 11 reviews
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
New place to stay
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, 79 reviews