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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Chicago River House – GIANT wall projector!
2 bedrooms, 2 beds, 2 private bathrooms
17–22 Aug
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4.96 out of 5 average rating, 205 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 100 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
Chic & Cozy Boho Vibe in Heart of Logan Square
4.96 out of 5 average rating, 76 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 341 reviews, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 303 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Guest favourite
Room in Chicago
Private Room & Shared Bathroom | Work Desk
4.91 out of 5 average rating, 33 reviews, 1 double bed, 2 bathrooms
15–20 Aug
Flat in Chicago
Sunny Logan Square home-away-from-home
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
4.97 out of 5 average rating, 494 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Chicago
Modern 1 BR Near the L, Beach - Bright and Sunny!
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
4.99 out of 5 average rating, 356 reviews, 3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Home in Chicago
Big house in the BEST Location!
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Sept
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
4.95 out of 5 average rating, 685 reviews, 3 beds, 1 bathroom
27 Nov – 2 Dec