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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 568 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
4.98 out of 5 average rating, 186 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 349 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
Elegant Modern-Luxury Condo in Popular West Town
4.95 out of 5 average rating, 247 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
Place to stay in Chicago
Guest room in Dunning, Chicago IL
New place to stay, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 234 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
4.93 out of 5 average rating, 120 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
4.95 out of 5 average rating, 260 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Chicago
Top Floor Escape | Modern Amenities | Lush Garden
4.97 out of 5 average rating, 493 reviews, 2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 88 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul