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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in West Loop
Spacious Downtown 3BR with Free Parking
3 bedrooms, 7 beds, 2 bathrooms
20–25 Nov
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4.92 out of 5 average rating, 167 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 74 reviews
Superhost
Flat in West Side
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
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
23–28 Sept
5.0 out of 5 average rating, 10 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 73 reviews
Guest favourite
Home in Beverly
Maison Blanc Noir ~ Chicago Mansion w/ King Beds
5 bedrooms, 8 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 27 reviews