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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Luxurious River North 3BR/2BA- Free Onsite Parking
3 bedrooms, 5 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.99 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
16–21 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
4–9 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
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
4.96 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 305 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Dec
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 342 reviews, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.91 out of 5 average rating, 111 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 126 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
4.94 out of 5 average rating, 252 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Oct