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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Chicago River House – GIANT wall projector!
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Sept
,
4.96 out of 5 average rating, 206 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 27 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
9–14 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 56 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, 525 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
27 Nov – 2 Dec
4.95 out of 5 average rating, 685 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 319 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Aug
4.93 out of 5 average rating, 107 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
8–13 Aug
New place to stay
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds
19–24 Oct
4.98 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
3–8 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from this Newly Remodeled Gem
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 274 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Chicago
An elegant Chicago Northside Getaway
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 374 reviews
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, 305 reviews
Guest favourite
Room in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 18 reviews