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Search results; Over 1,000 homes in Chicago

Superhost
Loft in Chicago
West Town Traveler's Lodge
2 bedrooms, 2 beds, 1 private bathroom
19–24 Sept
,
4.86 out of 5 average rating, 680 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 168 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, 29 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, 525 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
8–13 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
12–17 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 23 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
7–12 Sept
New place to stay
Top guest favourite
Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 62 reviews
Flat in Chicago
Bright & Cozy 1 Bdrm • Free Parking
1 bedroom, 2 beds
18–23 Oct
4.6 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
9–14 Nov
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 108 reviews