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Search results; Over 1,000 homes in Chicago

Guest favourite
Townhouse in Chicago
Old Town/Lincoln Park Luxury Home Garage & Rooftop
4 bedrooms, 6 beds, 2.5 private bathrooms
4–9 Oct
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4.91 out of 5 average rating, 185 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 59 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
6–11 Sept
New place to stay
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
14–19 Oct
4.88 out of 5 average rating, 445 reviews
Superhost
Flat in Chicago
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Sports Fans Welcome and Family Friendly
3 bedrooms, 8 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 258 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
Skandi Retreat
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.96 out of 5 average rating, 90 reviews
Flat in Chicago
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed, Parking, Deck, Yard
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 98 reviews