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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms4 beds, 3 bathrooms,
5–10 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms3 beds, 1 bathroom,
8–13 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms3 beds, 2 bathrooms,
3–8 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Oak Park
Treetop Oasis With Parking Walkable To Town+Train
2 bedrooms4 beds, 1 bathroom,
28 Jun – 3 Jul
4.97 out of 5 average rating, 79 reviews
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms3 queen beds, 1 bathroom,
21–26 Jun
New place to stay
Superhost
Flat in Chicago
Stunning Apt, walk to NEU, “The Bernard”
4 bedrooms3 beds, 1 bathroom,
26–31 Jul
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms2 beds, 2 bathrooms,
27 Jun – 2 Jul
4.95 out of 5 average rating, 155 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms3 beds, 2 bathrooms,
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms3 queen beds, 1.5 bathrooms,
28 Jun – 3 Jul
4.99 out of 5 average rating, 299 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms2 bathrooms,
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom1 bunk bed, 1 bathroom,
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms8 beds, 3 bathrooms,
23–28 Aug
4.9 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms2 queen beds, 1 bathroom,
9–14 Aug
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms3 beds, 2 bathrooms,
24–29 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom1 king bed, 1 bathroom,
20–25 Oct
5.0 out of 5 average rating, 50 reviews
Flat in Chicago
Garden Retreat Pilsen Chicago Apartment
2 bedrooms3 beds, 2 bathrooms,
29 Jun – 4 Jul
5.0 out of 5 average rating, 3 reviews
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms6 beds, 2 bathrooms,
21–26 Jun
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms3 beds, 1.5 bathrooms,
12–17 Jul
5.0 out of 5 average rating, 12 reviews