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Search results; Over 1,000 homes in Chicago

Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 private bathroom
21–26 Nov
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4.96 out of 5 average rating, 597 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, 126 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
15–20 Aug
4.87 out of 5 average rating, 15 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Guest favourite
Room in Chicago
ChicagoChinatownCenterB
1 single bed
25–30 Oct
4.93 out of 5 average rating, 59 reviews
Guest favourite
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed
16–21 Aug
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 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, 18 reviews
Top 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
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
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
1–6 Nov
4.99 out of 5 average rating, 137 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
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
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 6 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
6–11 Sept
New place to stay
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