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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
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms, 6 beds
22–27 Jun
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Oct
4.95 out of 5 average rating, 115 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
1–6 Jul
4.94 out of 5 average rating, 139 reviews
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
5–10 Jul
4.99 out of 5 average rating, 123 reviews
Guest favourite
Flat in Lockport
Bright Lockport Farmhouse: King Bed + Yard View
1 bedroom, 1 bed
20–25 Jun
4.98 out of 5 average rating, 43 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Jun – 2 Jul
4.96 out of 5 average rating, 156 reviews
Top guest favourite
Home in Chicago
Amazing Penthouse: Views, Hot Tub, Cold Plunge!
3 bedrooms, 8 beds
30 Jul – 4 Aug
4.94 out of 5 average rating, 400 reviews
Top guest favourite
Flat in Oak Park
Historic Hotspot: Downtown Oak Park w/parking spot
2 bedrooms, 2 queen beds
9–14 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
25–30 Oct
4.95 out of 5 average rating, 676 reviews
Top guest favourite
Flat in Chicago
Rustic Sanctuary
2 bedrooms, 2 queen beds
21–26 Jun
5.0 out of 5 average rating, 44 reviews
Place to stay in Chicago
10 minutes to Downtown near subway and bus m1
1 bedroom, 1 queen bed
13–18 Oct
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms, 3 queen beds
4–9 Oct
4.99 out of 5 average rating, 114 reviews
Featured hotel
Hotel in Chicago
Deluxe king room & rooftop bar with views
1 bedroom, 1 king bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Chicago
Sun-Soaked West Loop Penthouse/Private Rooftop/3BA
2 bedrooms, 4 beds
21–26 Jun
5.0 out of 5 average rating, 68 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
5–10 Jul
4.91 out of 5 average rating, 184 reviews