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Search results; Over 1,000 homes in Chicago

Apartment in Lincoln Park
Modern Luxury In Old Town - Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
10–15 Sept
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4.77 out of 5 average rating, 272 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Home in Edgewater
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Room in Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed
16–21 Aug
New place to stay
Apartment in Wicker Park
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
Flat in Irving Park
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
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Humboldt Park
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 Bridgeport
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 West Rogers Park
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
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
Superhost
Home in Portage Park
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds
8–13 Aug
New place to stay
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 58 reviews
Guest favourite
Flat in South Side
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
Top guest favourite
Home in Logan Square
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
16–21 Aug
4.97 out of 5 average rating, 494 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews