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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Modern+Spacious Inn Little Italy Near W Loop W/PKG
4 bedrooms, 4 beds, 2 private bathrooms
1–6 Nov
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4.99 out of 5 average rating, 335 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 98 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 125 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 83 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
4.89 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Superhost
Flat in Chicago
Renovated 2BR in Prime L. | Sleeps 6 |Pet Friendly
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
20–25 Sept
Top guest favourite
Apartment in Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4.97 out of 5 average rating, 34 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Nov
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 5 reviews, 1 king bed, 1 bathroom
10–15 Aug