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Search results; Over 1,000 homes in Chicago

Guest favourite
Loft in Chicago
Huge Downtown Penthouse #4 | Park, Museums +gym
1 bedroom, 4 beds, 1.5 private bathrooms
7–12 Sept
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4.8 out of 5 average rating, 278 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.87 out of 5 average rating, 15 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
4.95 out of 5 average rating, 127 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
Skyline Views • Rooftop • Free EV Garage Parking
2 bedrooms, 8 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 65 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
16–21 Aug
New place to stay
Superhost
Flat in Chicago
The Horizon | 3BR PH, 63rd Fl, Top Sky Deck
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Flat in Chicago
5 Minutes to Wrigley + Sauna + Games Free Parking
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
New place to stay
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 119 reviews