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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Downtown Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
13–18 Sept
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4.97 out of 5 average rating, 147 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
4.95 out of 5 average rating, 110 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 130 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Apartment in Lincoln Park
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 920 reviews
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
28 Nov – 3 Dec
4.94 out of 5 average rating, 258 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 312 reviews
Superhost
Flat in West Side
Bright Boutique Designer Unit in Vibrant Pilsen
1 bedroom, 1 single bed, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Apartment in Lincoln Park
1750 sq. ft. Pets OK | full Kitchen | Workspace
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 105 reviews
Guest favourite
Flat in West Town
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds, 2 bathrooms
1–6 Nov
4.9 out of 5 average rating, 299 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds, 2 bathrooms
15–20 Nov
4.97 out of 5 average rating, 208 reviews