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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
King Sleep Number Bed – No Cleaning Fee
1 bedroom, 1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.96 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Chicago
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Jan
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Chicago
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 254 reviews
Superhost
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
28 Nov – 3 Dec
4.96 out of 5 average rating, 312 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 29 reviews
Room in Elmhurst
Close to Oakbrook and O’Hare + Bistro. Pool. Gym.
2 double beds, 1 bathroom
19–24 Sept
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 66 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Apartment in Chicago
The Cozy Suite
2 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.86 out of 5 average rating, 69 reviews