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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
ALOHA Tropical Penthouse in Wicker Park Sleeps 14
4 bedrooms, 7 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.9 out of 5 average rating, 216 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 100 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
29 Nov – 4 Dec
Top guest favourite
Apartment in Chicago
Great location. Free parking.
4.97 out of 5 average rating, 908 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Oct
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
4.97 out of 5 average rating, 494 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 303 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 83 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 341 reviews, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chicago
Greystone Haven & Suite - Lux & Lush in Logan
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
Top guest favourite
Flat in Forest Park
Walk to Oak Park from a Cozy, Sun-soaked Hideaway
4.96 out of 5 average rating, 240 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Room in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 17 reviews, 1 king bed, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 6 reviews, 1 king bed, 1 bathroom
9–14 Aug
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
4.95 out of 5 average rating, 685 reviews, 3 beds, 1 bathroom
13–18 Oct
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
4.98 out of 5 average rating, 107 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Oct