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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Loop
Fulton Market Loft | Rooftop Fire Pit | Parking
3 bedrooms, 3 beds, 2.5 private bathrooms
22–27 Aug
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4.96 out of 5 average rating, 281 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
27 Sept – 2 Oct
4.91 out of 5 average rating, 58 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in West Side
Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
2 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 476 reviews
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 348 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Room in West Side
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
9–14 Aug
4.77 out of 5 average rating, 568 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Apartment in Lake View
Bright, new 2BR in the heart of East Lakeview
2 bedrooms, 3 beds
23–28 Aug
4.99 out of 5 average rating, 128 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 54 reviews
Guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
12–17 Jul
4.91 out of 5 average rating, 106 reviews
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
7–12 Sept
4.95 out of 5 average rating, 65 reviews