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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Ravenswood Guest House Annex
1 bedroom, 3 beds, 1 bathroom
23–28 Oct
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4.93 out of 5 average rating, 494 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
New place to stay, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 524 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Flat in Chicago
Sunny Logan Square home-away-from-home
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
5.0 out of 5 average rating, 88 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 303 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
4.97 out of 5 average rating, 494 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 83 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 126 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
4.93 out of 5 average rating, 340 reviews, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
5.0 out of 5 average rating, 37 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Jan
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug