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4 Jul - 6 Jul
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25 Jul - 27 Jul
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Apartments in Westchester

Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.8 out of 10, Exceptional, (9)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Fridge, microwave, oven, stovetop

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

8.8 out of 10, Excellent, (26)
"Great location, cute place."
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Interior

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.2 out of 10, Very Good, (17)
"The property was excellent, for my stay "
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Serene 3-bedroom apartment in Chicago
Smart TV

Serene 3-bedroom apartment in Chicago

9.6 out of 10, Exceptional, (5)
Serene 3-bedroom apartment in Chicago
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (30)
"Fun 1br stay. Great for a getaway or weekend stay."
The price is SAR 544
SAR 1,223 total
includes taxes & fees
27 Jun - 28 Jun
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Spacious apartment in awesome Chicago with WiFi, AC
Terrace/patio

Spacious apartment in awesome Chicago with WiFi, AC

10.0 out of 10, Exceptional, (3)
"Very clean and considerate of the small necessities. Family friendly neighborhood and very close to many attractions. Also good communication with the host. Will be returning soon!! "
Spacious apartment in awesome Chicago with WiFi, AC
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (54)
"This property was clean, and the host provided clear instructions for access. I reached out to the host/owner and they were immediately responsive. Overall a great experience."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (22)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (26)
"Easy to find, slept like a baby. "
The price is SAR 503
SAR 1,218 total
includes taxes & fees
29 Jun - 30 Jun
2-bedroom apartment just 2 minutes drive to Wrigley Field
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (1)
"The location was perfect. It was clean and just as pictured. For a studio, it had plenty of room. "
The price is SAR 488
SAR 894 total
includes taxes & fees
8 Jul - 9 Jul
Relaxing Chicago Studio
Animal House Near Sox Stadium
Terrace/patio

Animal House Near Sox Stadium

9.6 out of 10, Exceptional, (4)
" Cute place. Ideal setup up for your pets. Great location."
Animal House Near Sox Stadium
10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT
Fridge, microwave, oven, stovetop

10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT

8.0 out of 10, Very Good, (17)
"Stayed over thanksgiving holiday. Little kitchen was perfect with all the tools needed. Rooms and beds were cozy and the location was perfect. "
10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT
Beautiful 1BR Home in Historic Hyde Park Near University of Chicago
Smart TV

Beautiful 1BR Home in Historic Hyde Park Near University of Chicago

10.0 out of 10, Exceptional, (1)
"This apartment is exactly as advertised. It is spacious for a one bedroom with a decent sized kitchen, a dining room table and a cozy living room area with a smart TV that allowed us to log in to all our different streaming services. The king-sized bed is quite comfortable. The apartment is in an older building with cast iron heaters, so if you aren't used to those, be warned they can be noisy, but they do keep the apartment toasty warm in the winter.The location is excellent. Only a block from...
Beautiful 1BR Home in Historic Hyde Park Near University of Chicago
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Food and drink

Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

2.0 star property
9.6 out of 10, Exceptional, (5)
"The apartment was what I needed for a few days stay while in town for the Chicago marathon. Convenient to public transportation to Downtown. Located in a beautiful historic neighborhood and close to grocery store and eateries. Host was very communicative and access was easy."
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
2 bedrooms, iron/ironing board, WiFi, bed sheets

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

8.8 out of 10, Excellent, (18)
"This is a very nice place to stay lo ation in convenient. Only issue is that its kinda noisy you can hear train and traffic. "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Comfort/Clean!: Free Parking 15 min ORD/Downtown3
Fridge, microwave, oven, stovetop

Comfort/Clean!: Free Parking 15 min ORD/Downtown3

8.6 out of 10, Excellent, (16)
"The place was clean and cozy. "
Comfort/Clean!: Free Parking 15 min ORD/Downtown3
Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
Private kitchen

Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago

10.0 out of 10, Exceptional, (2)
"My trip was the best place was nicè will book again"
Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Beach nearby

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

9.6 out of 10, Exceptional, (7)
"Very nice cozy little apartment. Contactless check in and the instructions provided were clear and simple. Parked in a Spot Hero lot about a quarter mile north of the apartment. There were plenty of spots left when we got there and left so that was cheap and convenient. We only stayed here to sleep after a concert so we didn't really use any amenities or anything so I can't speak to that. There were some reviews about thin walls but the neighbors apparently weren't home or are very quiet because...
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking
Smart TV, fireplace, books

4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking

9.4 out of 10, Exceptional, (10)
"Clean, cool sports memorabilia, great location!"
4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking
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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Frequently asked questions

What's it like to stay at an apartment in Westchester?
There are plenty of places to stay with in the larger Chicago area, with 5267 lodging choices including 2620 apartments. You might want to visit the area's shops and enjoy its restaurants. Discover top sights in the region such as Wrigley Field and Michigan Avenue.
Are you thinking about an apartment for your stay?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families who want the conveniences of home.
What can I expect from the weather in Westchester?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Westchester. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What should I see and do in Westchester?
Westchester is known for its restaurants and shops. Explore the area and family-friendly sights such as Galloping Ghost, or get out into nature at a spot like Millennium Park. You'll find favorite places to visit like Wrigley Field and Michigan Avenue in the larger area.
What's the best way to get to and around Westchester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) from the heart of the city. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.