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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
South Loop 3BD 2BA Condo with Balcony and Parking
3 bedrooms, 3 beds, 2 private bathrooms
26 Sept – 1 Oct
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4.93 out of 5 average rating, 237 reviews
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
Top guest favourite
Flat in Forest Park
Like a Treehouse!
5.0 out of 5 average rating, 377 reviews, 1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
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
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 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
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
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
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 4 reviews, 1 king bed, 1 bathroom
9–14 Aug
Guest favourite
Flat in Chicago
Cozy Square Stay | Quiet & Private
4.81 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 1 bathroom
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
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
Top guest favourite
Guest suite in Chicago
Studio 15 Minutes From Ohare!
4.97 out of 5 average rating, 202 reviews, 1 bed, 1 bathroom
23–28 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
The Logan Square Guest House (Free Parking!)
4.99 out of 5 average rating, 94 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
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