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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Gamers Getaway 20 minutes from downtown
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Jul
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4.85 out of 5 average rating, 155 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 17 beds, 3.5 bathrooms
3–8 Jul
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
New place to stay
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 337 reviews
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.97 out of 5 average rating, 78 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Home in Chicago
Blonde Beauty Cozy Home Near Downtown Attractions
4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
3 bedrooms, 1 bathroom
24–29 Jul
4.94 out of 5 average rating, 163 reviews
Guest favourite
Flat in Chicago
Cozy Urban View Retreat Near Downtown - Sleeps 7
2 bedrooms, 4 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 140 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Chicago
Gold Coast Home|Rooftop |PoolTable |Parking |Views
4 bedrooms, 6 beds, 4.5 bathrooms
5–10 Jul
4.89 out of 5 average rating, 63 reviews