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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Cozy Andersonville Cabin
1 bedroom, 2 beds, 1 private bathroom
3–8 Feb
,
4.98 out of 5 average rating, 169 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
16–21 Aug
4.9 out of 5 average rating, 128 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
16–21 Aug
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
14–19 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
14–19 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
1–6 Nov
4.99 out of 5 average rating, 137 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 18 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds
7–12 Sept
New place to stay
Superhost
Flat in Chicago
Luxury Penthouse Collection PH2 - Fulton Market
1 bedroom, 2 beds
1–6 Sept
New place to stay
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews