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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Travelers Retreat in Old Town Chicago
1 bedroom, 2 beds, 1 private bathroom
22–27 Aug
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4.99 out of 5 average rating, 143 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
7–12 Sept
New place to stay
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
20–25 Sept
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.89 out of 5 average rating, 136 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
16–21 Feb
5.0 out of 5 average rating, 39 reviews
Flat in Forest Park
Family-Friendly Apt for 4 w/Parking, Near City+MDW
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 105 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.88 out of 5 average rating, 441 reviews
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 22 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Room in Chicago
Private bdr | Free garage parking | No fees
1 queen bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
24–29 Nov
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 36 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 95 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 310 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.95 out of 5 average rating, 87 reviews