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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Ukrainian Village 3BR/3BA • Private Patio, Parking
3 bedrooms, 4 beds, 3 private bathrooms
17–22 Aug
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4.98 out of 5 average rating, 120 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
2–7 Aug
New place to stay
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
15–20 Nov
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
16–21 Aug
4.92 out of 5 average rating, 524 reviews
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 27 reviews
Flat in Chicago
Sunny Logan Square home-away-from-home
2 bedrooms, 2 beds
1–6 Nov
New place to stay
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
7–12 Sept
4.97 out of 5 average rating, 494 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
20–25 Sept
New place to stay
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 303 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 126 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 83 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
16–21 Aug
4.93 out of 5 average rating, 341 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from this Newly Remodeled Gem
2 bedrooms, 3 beds
7–12 Sept
4.99 out of 5 average rating, 274 reviews