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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Bronzeville Beauty: Modern Style + Historic Charm
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.94 out of 5 average rating, 233 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
20–25 Sept
4.92 out of 5 average rating, 38 reviews
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.95 out of 5 average rating, 44 reviews
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
26 Sept – 1 Oct
New place to stay
Guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds
25–30 Oct
4.96 out of 5 average rating, 135 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 519 reviews
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
9–14 Nov
4.97 out of 5 average rating, 630 reviews
Flat in Chicago
Chic 4BR South Loop Urban Retreat Near McCormick
4 bedrooms, 5 beds
8–13 Sept
New place to stay
Guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds
7–12 Sept
4.94 out of 5 average rating, 580 reviews
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.88 out of 5 average rating, 76 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 72 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
20–25 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews