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Check prices for these dates

In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Condo Rentals in Westchester

Our top choices for Westchester condo rentals

Chic Urban Retreat Near Wrigley Field w/Parking
Exterior detail

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (34)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
Chic Urban Retreat Near Wrigley Field w/Parking
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Terrace/patio

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Gorgeous 3BR River North Condo - Free Parking
Fridge, microwave, oven, stovetop

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (21)
"House was very accommodating and well stocked for a family of 4 including two teenage children. Check in was easy and as described, and location was easy walking distance to restaurants and shopping. Would definitely stay here again when in Chicago!"
Gorgeous 3BR River North Condo - Free Parking
Elizabeth by Coast to Cactus | Chic Artists Loft
Interior

Elizabeth by Coast to Cactus | Chic Artists Loft

9.2 out of 10, Wonderful, (21)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (111)
"This property had all the comforts we needed and is in a great location. Would absolutely love to stay there again!"
Stunning 3 BR in prime Chicago location
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Fridge, microwave, oven, stovetop

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.6 out of 10, Exceptional, (44)
"It was a great place to stay and very spacious!"
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Fridge, microwave, oven, stovetop

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.6 out of 10, Exceptional, (38)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood
Fridge, microwave, oven, stovetop

Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood

8.6 out of 10, Excellent, (19)
"This place was clean and host was very nice"
Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood
Spacious & Comfortable 3 Bedrooms + Bonus Room
4 bedrooms, desk, iron/ironing board, free WiFi

Spacious & Comfortable 3 Bedrooms + Bonus Room

6.0 out of 10, (2)
"Property is very nice and as described in the listing. We enjoyed the space especially with a family of 5. Parking is snug but not a big deal, may be just our inexperience - but a good heads up!"
The price is SAR 766
SAR 2,137 total
includes taxes & fees
22 Sep - 23 Sep
Spacious & Comfortable 3 Bedrooms + Bonus Room
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

8.8 out of 10, Excellent, (13)
"I thought this place was so cute, loved the outset deck! Was spacious and the host was very nice and helpful when needed! Would stay again for sure! "
Modern Condo-Obama & University of Chicago Area
NEW LUXURY CONDO WITH PATIO DECK
Property grounds

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (179)
"Wonderful place to stay. We would stay there again. "
NEW LUXURY CONDO WITH PATIO DECK
Spacious, Clean and Steps from Wrigley Field!
Private kitchen

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (22)
"Great stay in Wrigleyville. Steps to the park and all the entertainment. Would definitely stay again. "
Spacious, Clean and Steps from Wrigley Field!
Chic Suite/Mins to L Train /Laundry/Free Parking
Fridge, microwave, oven, stovetop

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (52)
"Good location. "
Chic Suite/Mins to L Train /Laundry/Free Parking
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
Interior

MICH AVE #23 2bd/2ba Downtown, Museums w/ Views

9.8 out of 10, Exceptional, (24)
"It was perfect and everything as promised. "
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
The Exclusive- 7 Bed, 6 Bath Retreat
Smart TV, computer monitors

The Exclusive- 7 Bed, 6 Bath Retreat

9.6 out of 10, Exceptional, (19)
"This was exactly whatv we were looking for. Great location."
The Exclusive- 7 Bed, 6 Bath Retreat
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Fridge, microwave, oven, dishwasher

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

10.0 out of 10, Exceptional, (35)
"Wonderful location and home. Thanks to our hosts!"
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Dining

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Comfortable Condo in the Heart of Bronzeville by RedAwning
Fridge, microwave, oven, coffee/tea maker

Comfortable Condo in the Heart of Bronzeville by RedAwning

7.2 out of 10, Good, (5)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
Comfortable Condo in the Heart of Bronzeville by RedAwning
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"We had a great time and the property manager was very thoughtful. It was a very cute apartment and great location very close to Loyola."
Walking distance to restaurants, shops and Lake Michigan,
Luxuriant, Foodie, Culture,
Property grounds

Luxuriant, Foodie, Culture,

9.4 out of 10, Exceptional, (24)
"Perfect location, condo was amazing. Thank you very much!"
Luxuriant, Foodie, Culture,
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Everything just fantastic at the Palmer house! A must place to stay in Chicago!"
Rodney 1-night trip
Posted 3 days ago
Palmer House a Hilton Hotel

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