Search Apartments in Westchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 1855 Apartments in Westchester with updated reviews, rates, and availability.

Sonder Onterie
Terrace/patio

Sonder Onterie

3.5 star property
8.4 out of 10, Very Good, (13)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is AED 613
AED 720 total
includes taxes & fees
30 Apr - 1 May
Sonder Onterie
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
3 bedrooms, WiFi, bed sheets

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

9.2 out of 10, Wonderful, (76)
"The home made our stay in Chicago very easy. There is a lot to do nearby and easy to walk everywhere. The place is very nice and amenable."
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
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, (46)
"This property is very clean and very cozy. The location is great, except at night, I was able to hear the train and highway traffic. My husband wasn't bothered at all. We still liked it and suited our needs. The amenities were excellent. There's plenty of parking. "
Chic, Cozy home, by Blue Line Train Stop + Free parking
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
9.6 out of 10, Exceptional, (10)
"What a cosy quaint place! Everyone was friendly. "
The price is AED 364
AED 947 total
includes taxes & fees
21 Apr - 22 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
Charming Wrigleyville Home Close to the Cubs!
Microwave

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (18)
"Hardest part of the experience was finding the front door. After that, we had a wonderful experience. The shower was awesome. "
Charming Wrigleyville Home Close to the Cubs!
Walk to Wrigley Field/Monthly Discounts Available
Fridge, microwave, oven, stovetop

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (137)
"we had a family stay for Opening Day at Wrigley. Super location for Wrigley . Great Host. very good communicator "
Walk to Wrigley Field/Monthly Discounts Available
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (33)
"What an exceptional property! Perfect for a two-person getaway. It's right around the corner from shops and restaurants in the terrific Gold Coast neighborhood. Beautiful, modern decor with vintage building charm. It is very safe, quiet and comfortable - we got great sleep here. The host was communicative and everything was very easy. Definitely plan to come back to this gem!"
Chic & Historic Apartment Steps from Mag Mile
Remodeled West Loop Apartment Near United Center
Interior

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (34)
"Everything was nice and neat. They were super easy to communicate with. We had a little issue with the main building door keyless entry. Other than that everything was great."
Remodeled West Loop Apartment Near United Center
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Smart TV, DVD player, books, stereo

Stylish, Inviting 2-BR near Logan Square and Wrigley Field

10.0 out of 10, Exceptional, (47)
"Clean, safe, excellent "
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Cozy, Comfortable and Convenient apartment. Close to everything!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (57)
"My husband, daughter and I went to Chicago for a weekend getaway and this place was clean, cute and so close to transit. Great place for a small family to stay. "
The price is AED 441
AED 1,013 total
includes taxes & fees
20 Apr - 21 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Smart TV, fireplace, DVD player, books

The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

10.0 out of 10, Exceptional, (25)
"Hosts are very responsive. Super easy checkout. The rental has lots of space, is comfortable and is very clean. This was our second time staying there and we hope it will be available the next time we come to visit that area of Chicago!"
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Terrace/patio

Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

9.8 out of 10, Exceptional, (18)
"Very clean, loved all the thoughtful extras!"
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Property grounds

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

8.8 out of 10, Excellent, (8)
"Property was great. "
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Bright Garden Studio
Interior

Bright Garden Studio

9.0 out of 10, Wonderful, (21)
"Great Location"
The price is AED 360
AED 953 total
includes taxes & fees
21 Apr - 22 Apr
Bright Garden Studio
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (97)
"Just what we needed for our Beauty show convention in Rosemont. Great place, the host Jamie is awesome. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Dramatic, Spacious Wrigley Loft + Private Rooftop, Grill - Ranked GUEST FAVORITE
Fridge, microwave, oven, stovetop

Dramatic, Spacious Wrigley Loft + Private Rooftop, Grill - Ranked GUEST FAVORITE

10.0 out of 10, Exceptional, (87)
"Property and location were great! Very responsive to questions and check in and out were easy."
Dramatic, Spacious Wrigley Loft + Private Rooftop, Grill - Ranked GUEST FAVORITE
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Fridge, microwave, oven, stovetop

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

9.6 out of 10, Exceptional, (81)
"We enjoyed our stay. Ali was prompt and clear with communication. It was a little confusing when arriving but I feel it was due to our late arrival and it was difficult to see due to lighting. Overall the stay was good for a little getaway. Also the tenants in the building were friendly. "
The price is AED 444
AED 889 total
includes taxes & fees
20 Apr - 21 Apr
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (57)
"This was the second time we have stayed at this property. We like everything about it. Clean property, plenty of room, cool outlooks from the windows, all the amenities. And the neighborhood has plenty of restaurants, coffee shops, well located to other parts of town. And even a very convenient parking space. Highly recommend it. Lastly, the property manager is very responsive and friendly and helpful. "
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Interior

McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests

McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Animal House Near Sox Stadium
Terrace/patio

Animal House Near Sox Stadium

9.0 out of 10, Wonderful, (2)
"Stayed over Vday weekend— no complaints, space was nice and served my needs perfectly. Had lots of animal/pet related decor and gave the space a nice aesthetic. Owner was communicative and easy to work with! The space had nice amenities like towels, linens, projector, appliances, and etc. Neighborhood was very cute too, walking distance to a bunch of restaurants. "
Animal House Near Sox Stadium
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.
Don't see what you're looking for?
See all available properties in Westchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Westchester

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (727)
"Great family place to stay. "
The price is AED 403
AED 581 total
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue
Sonder South Wabash
36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (472)
"Good place"
The price is AED 429
AED 503 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (271)
"Very clean l, quiet and well thought out. Had everything we needed and the bed was super comfortable! Great having a 12 cup coffee pot! Parking was close and although not a lot of close options to restaurants or shopping, there were many more options within a 15-20 min walk. Would definitely stay here again!"
The price is AED 473
AED 555 total
includes taxes & fees
21 Apr - 22 Apr
Sonder Market Hall
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.

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 4929 lodging choices including 2490 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's the top apartment for a stay in Westchester?
Below you’ll find a top apartment in the area: Sonder Onterie: Situated in Chicago, 13.9 mi/22.4 km from the heart of Westchester.
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.