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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Downtown Chicago
Travelers Retreat in Old Town Chicago
1 bedroom, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.99 out of 5 average rating, 146 reviews
Featured hotel
Hotel in Downtown Chicago
Junior two bedroom suite
2 bedrooms
18–23 Oct
Featured hotel
Hotel in Downtown Chicago
Level studio suite
1 bedroom
17–22 Sept
Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds
24–29 Sept
4.92 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
2–7 Jan
4.97 out of 5 average rating, 87 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 133 reviews
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds
28 Nov – 3 Dec
4.97 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 262 reviews
Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
14–19 Nov
4.92 out of 5 average rating, 75 reviews