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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
13–18 Sept
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4.97 out of 5 average rating, 147 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 38 reviews
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
22–27 Feb
5.0 out of 5 average rating, 39 reviews
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
26 Sept – 1 Oct
New place to stay
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 27 reviews
Flat in Chicago
Chic 4BR South Loop Urban Retreat Near McCormick
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 630 reviews
Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 580 reviews
Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
7–12 Nov
4.9 out of 5 average rating, 519 reviews
Top guest favourite
Flat in Chicago
Stylish 2BR stunner w/ unbeatable location
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 203 reviews
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds, 2 bathrooms
22–27 Oct
4.88 out of 5 average rating, 76 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 11 reviews
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds, 3.5 bathrooms
24–29 Sept
4.93 out of 5 average rating, 14 reviews