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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, 301 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 queen beds
22–27 Aug
New place to stay
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 beds
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 queen bed
22–27 Jul
4.97 out of 5 average rating, 93 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 queen beds
26–31 Jul
New place to stay
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5 beds
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Room in Chicago
Stay with Nick
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
27 Nov – 2 Dec
4.95 out of 5 average rating, 681 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
3 beds
16–21 Aug
4.88 out of 5 average rating, 434 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 beds
26–31 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Room in Chicago
Stay with Charles
Historic North Park home
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
3 beds
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
4 beds
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
5 beds
21–26 Sept
4.9 out of 5 average rating, 505 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 beds
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Place to stay in Chicago
J33. Next to downtown private room in shared apt
1 bed
19–24 Jul
New place to stay
Guest favourite
Room in Chicago
Stay with Atakan
Private Room & Shared Bathroom | Work Desk
15–20 Aug
4.91 out of 5 average rating, 32 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
3 queen beds
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
15 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews