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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Ukrainian Village 3BR/3BA • Private Patio, Parking
3 bedrooms, 4 beds, 3 private bathrooms
17–22 Aug
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4.98 out of 5 average rating, 120 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
4.95 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
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
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
4.98 out of 5 average rating, 410 reviews, 2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4.8 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 3 bathrooms
9–14 Nov
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
15–20 Aug
Guest favourite
Flat in Chicago
Cozy Square Stay | Quiet & Private
4.9 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 316 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 6 reviews, 1 king bed, 1 bathroom
10–15 Aug
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
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
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
4.92 out of 5 average rating, 523 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
The Avondale Garden Unit
4.87 out of 5 average rating, 375 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
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
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
4.98 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 125 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Room in Chicago
Private Room Near Hyde Park & Beach
New place to stay, 1 queen bed, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
4.92 out of 5 average rating, 249 reviews, 3 bedrooms, 5 beds, 1 bathroom
23–28 Aug