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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
19–24 Jul
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4.97 out of 5 average rating, 136 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, 116 reviews
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
30 Jun – 5 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 230 reviews
Flat in Chicago
Cozy Apartment in Pilsen | 2BR 2B | 15 Min to Town
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Guest favourite
Apartment in Chicago
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jun
4.97 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Parking & Walkability
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 81 reviews
Guest favourite
Flat in Chicago
4 Bedroom Penthouse Loft in Heart of Wicker Park
4 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 6 reviews
Home in Chicago
Comfortable welcoming stay for business or leisure
3 bedrooms, 4 beds, 1 bathroom
26 Jun – 1 Jul
New place to stay
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Luxe Wrigley Estate: Pool Table + Parking + Patio
4 bedrooms, 7 beds, 2 bathrooms
22–27 Jun
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Jun – 3 Jul
4.99 out of 5 average rating, 299 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 123 reviews