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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Studio 15 Minutes From Ohare!
Studio, 1 bed, 1 private bathroom
1–6 Nov
,
4.97 out of 5 average rating, 203 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 126 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
7–12 Aug
New place to stay
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
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
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 439 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
10–15 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
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 13 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, 68 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
1–6 Nov
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
9–14 Aug
4.91 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
26–31 Dec
4.99 out of 5 average rating, 108 reviews
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
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds
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
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews