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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
The Lakefront Lookout (Rooftop Deck • Gym)
2 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
,
4.81 out of 5 average rating, 232 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
15–20 Nov
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 377 reviews
Flat in Chicago
Sunny Logan Square home-away-from-home
2 bedrooms, 2 beds
1–6 Nov
New place to stay
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 55 reviews
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
21–26 Aug
4.94 out of 5 average rating, 16 reviews
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
2 bedrooms, 2 beds
7–12 Sept
4.97 out of 5 average rating, 494 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
15–20 Aug
New place to stay
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
Cozy Square Stay | Quiet & Private
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.81 out of 5 average rating, 21 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 303 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed
16–21 Aug
4.92 out of 5 average rating, 524 reviews
Top guest favourite
Guest suite in Chicago
Studio 15 Minutes From Ohare!
1 queen bed
23–28 Aug
4.97 out of 5 average rating, 202 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
The Logan Square Guest House (Free Parking!)
2 bedrooms, 2 queen beds
9–14 Aug
4.99 out of 5 average rating, 94 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay