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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Boutique Garden Suite • Pilsen • 10 Min to Loop
1 bedroom, 1 bed, 1 private bathroom
1–6 Jul
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4.95 out of 5 average rating, 220 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds
23–28 Aug
New place to stay
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Chicago
Modern 4BR West Town Duplex | Best for LongStays
4 bedrooms, 6 beds
1–6 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
3–8 Jul
5.0 out of 5 average rating, 12 reviews
Home in Chicago
Designer Home | Steps to the Obama Center & Beach
5 bedrooms, 10 beds
1–6 Jul
New place to stay
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 8 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, 678 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds
1–6 Jul
New place to stay
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
5–10 Jul
5.0 out of 5 average rating, 15 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, 188 reviews
Guest house in Chicago
Upscale Wicker Park Retreat
4 bedrooms, 8 beds
12–17 Jul
New place to stay
Place to stay in Chicago
Happy Homes U&I – Quiet Basement Retreat
1 bedroom, 1 bed
1–6 Jul
New place to stay
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
21–26 Sept
4.98 out of 5 average rating, 129 reviews