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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Penthouse Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
30 Sept – 5 Oct
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4.78 out of 5 average rating, 240 reviews
Featured hotel
Hotel in Chicago
Junior two bedroom suite
2 bedrooms, 1 bathroom
18–23 Oct
Featured hotel
Hotel in Chicago
Level studio suite
1 bedroom, 1 bathroom
17–22 Sept
Featured hotel
Hotel in Chicago
Deluxe double
1 bedroom, 2 double beds, 1 bathroom
24–29 Sept
4.92 out of 5 average rating, 62 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 133 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 32 reviews
Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 61 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3 bathrooms
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
14–19 Nov
4.92 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Chicago
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds, 2 bathrooms
6–11 Jan
4.9 out of 5 average rating, 302 reviews
Guest favourite
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed, 1 bathroom
18–23 Nov
4.95 out of 5 average rating, 100 reviews
Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 262 reviews
Top guest favourite
Flat in Chicago
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Jan
4.97 out of 5 average rating, 87 reviews
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
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