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Search results; Over 1,000 homes in Chicago

Superhost
Loft in Chicago
Spacious Downtown Penthouse | vintage, balcony&gym
1 bedroom, 4 beds, 1.5 private bathrooms
10–15 Aug
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4.71 out of 5 average rating, 224 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jan
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.95 out of 5 average rating, 100 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
Top guest favourite
Apartment in Chicago
Great location. Free parking.
4.97 out of 5 average rating, 908 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Oct
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 305 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Dec
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Chicago
Fulton House #1 (2bd/ 1ba)
4.95 out of 5 average rating, 111 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
30 Aug – 4 Sept