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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Bold Ukrainian Village 2 Bedroom w/Garage Parking
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
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4.86 out of 5 average rating, 324 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
16–21 Aug
4.9 out of 5 average rating, 129 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
16–21 Aug
4.87 out of 5 average rating, 15 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
1–6 Jan
4.95 out of 5 average rating, 127 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds
7–12 Sept
New place to stay
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, 18 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
16–21 Aug
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Flat in Chicago
The Horizon | 3BR PH, 63rd Fl, Top Sky Deck
3 bedrooms, 4 beds
16–21 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
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
14–19 Dec
4.99 out of 5 average rating, 108 reviews