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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Luxurious River North 3BR/2BA- Free Onsite Parking
3 bedrooms, 5 beds, 2 private bathrooms
26–31 Jul
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4.99 out of 5 average rating, 167 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
4–9 Jul
4.95 out of 5 average rating, 41 reviews
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
5–10 Jul
4.98 out of 5 average rating, 81 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 3 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
New place to stay
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
4 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Home in Chicago
Modern 3BR Near Obama Center, UChicago & McCormick
3 bedrooms, 3 queen beds
14–19 Jul
New place to stay
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
15–20 Aug
4.95 out of 5 average rating, 64 reviews
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Guest favourite
Home in Norridge
Modern Ranch | 5 Min to O'Hare, 25 to Chicago
3 bedrooms, 3 beds
18–23 Jul
4.92 out of 5 average rating, 13 reviews