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Search results; Over 1,000 homes in Chicago

Guest favourite
Loft in Chicago
Downtown Penthouse #5 | Vintage +gym & balcony
1 bedroom, 4 beds, 1.5 private bathrooms
29 Aug – 3 Sept
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4.76 out of 5 average rating, 259 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
12–17 Aug
4.9 out of 5 average rating, 126 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds
7–12 Sept
New place to stay
Place to stay in Chicago
Charming Room in Historic Ukrainian Village!
1 bedroom, 1 queen bed
6–11 Sept
New place to stay
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
15–20 Aug
4.87 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
20–25 Sept
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds
23–28 Oct
4.98 out of 5 average rating, 415 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Oak Park
A Quiet Stay While You Are Away Oak Park
2 bedrooms, 2 queen beds
1–6 Nov
4.95 out of 5 average rating, 205 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 55 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds
1–6 Nov
4.94 out of 5 average rating, 474 reviews
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Guest suite in Bensenville
Private, modern room near O’hare.
1 bedroom, 1 queen bed
22–27 Aug
New place to stay
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
16–21 Aug
4.87 out of 5 average rating, 15 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, 384 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 87 reviews