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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Edgewater
Ravenswood Guest House Annex
1 bedroom, 3 beds, 1 bathroom
15–20 Oct
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4.93 out of 5 average rating, 490 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.98 out of 5 average rating, 80 reviews
Superhost
Home in Ukrainian Village
Cozy Luxury Escape Amazing location private home
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
New place to stay
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
4.95 out of 5 average rating, 107 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Home in West Town
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
3–8 Jul
New place to stay
Top guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 17 beds, 3.5 bathrooms
3–8 Jul
4.95 out of 5 average rating, 41 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds, 3.5 bathrooms
3–8 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 64 reviews
Apartment in Wicker Park
Luxury Oasis in the Heart of the City w Roof Deck
3 bedrooms, 3 beds, 3 bathrooms
5–10 Jul
New place to stay