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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
26–31 Oct
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4.98 out of 5 average rating, 307 reviews
Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
6–11 Dec
New place to stay
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 60 reviews
Superhost
Guest suite in Chicago
Patio + FirePit • Park Free • Near Train & Dogs OK
2 bedrooms, 2 queen beds
3–8 Oct
New place to stay
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 32 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 75 reviews
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.89 out of 5 average rating, 81 reviews
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
Top guest favourite
Home in Chicago
Family Home in Bucktown | Parking | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
27 Nov – 2 Dec
4.95 out of 5 average rating, 197 reviews
Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds
13–18 Dec
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
19–24 Oct
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds
28 Oct – 2 Nov
4.95 out of 5 average rating, 273 reviews