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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 beds, 1.5 private bathrooms
20–25 Sept
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4.99 out of 5 average rating, 303 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
18–23 Jan
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
1–6 Aug
4.95 out of 5 average rating, 100 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 908 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
11–16 Aug
New place to stay
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
2 bedrooms, 2 queen beds
2–7 Aug
4.95 out of 5 average rating, 111 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
13–18 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
14–19 Sept
4.97 out of 5 average rating, 494 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
17–22 Sept
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
3–8 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 12 reviews