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Search results; Over 1,000 homes in Chicago

Guest suite in Chicago
Comfy/Private Entry & Bath/Free Parking - Win Win!
1 bedroom, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.8 out of 5 average rating, 358 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.95 out of 5 average rating, 104 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 25 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds, 2 bathrooms
17–22 Sept
New place to stay
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 494 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 111 reviews
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
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
15–20 Aug
4.91 out of 5 average rating, 111 reviews
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
10–15 Nov
4.96 out of 5 average rating, 317 reviews