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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Luxe, Private Suite w/Own Entrance-2023 Renovated
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
,
4.94 out of 5 average rating, 433 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Superhost
Home in Chicago
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds
8–13 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
16–21 Aug
New place to stay
Guest favourite
Room in Chicago
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
1 queen bed
28 Sept – 3 Oct
4.94 out of 5 average rating, 52 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 24 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
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, 24 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Post-Punk & Industrial Museum Apt - 4BR Bridgeport
4 bedrooms, 5 beds
8–13 Aug
5.0 out of 5 average rating, 29 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
16–21 Aug
4.97 out of 5 average rating, 494 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds
11–16 Dec
4.94 out of 5 average rating, 577 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 118 reviews