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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds, 2 private bathrooms
2–7 Nov
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4.88 out of 5 average rating, 489 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 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
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 168 reviews
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, 188 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds, 3.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 138 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 99 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 5 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, 83 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 82 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 32 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