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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
4 bedrooms, 7 beds, 3 private bathrooms
7–12 Aug
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4.92 out of 5 average rating, 198 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 118 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
26–31 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
4.9 out of 5 average rating, 42 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 4 reviews