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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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

Sonder Onterie
Miscellaneous

Sonder Onterie

3.5 star property
8.4 out of 10, Very Good, (15)
"Nice quiet stay. The rooms are beautiful!"
The price is AED 507
AED 595 total
includes taxes & fees
26 May - 27 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, (80)
"Nice property, enjoyed the stay."
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, (50)
"Just as described and fit our needs perfectly. Super clean"
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, (14)
"Great time and location. "
The price is AED 364
AED 959 total
includes taxes & fees
19 May - 20 May
2-bedroom apartment just 2 minutes drive to Wrigley Field
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (19)
"This place was perfect for us, and right where we needed it to be. "
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, (141)
"Clean and great location "
Walk to Wrigley Field/Monthly Discounts Available
Remodeled West Loop Apartment Near United Center
Interior

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (37)
"Overall a great place that was super convenient, comfortable, and exactly what we were looking for!"
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, (48)
"Great neighborhood and communicative host! Would stay again"
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Cozy, Comfortable and Convenient apartment. Close to everything!
Smart TV, books

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (59)
"Amazing place and clean"
The price is AED 441
AED 1,009 total
includes taxes & fees
20 May - 21 May
Cozy, Comfortable and Convenient apartment. Close to everything!
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Fridge, microwave, oven, stovetop

Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay at Toby's place. The property is as listed, very accommodating, everything we needed was provided! The host was very responsive within minutes of contacting. The place was very clean and well kept! The bed is very comfortable however if sleeping with a partner you will feel their every move. Parking can be difficult if you stay out late! If you can't find a spot on belle plaine try whipple. Would definitely stay here again. "
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
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, (26)
"Great stay and location!"
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!

9.4 out of 10, Exceptional, (20)
"Really nice space for an extended stay. Clean and thoughtfully decorated. Has all of the amenities you need."
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, (9)
"This lovely apartment was a great location for our family. Close to shops and restaurants. Easy walk to the Red Line train. The place was well stocked with bedding and the mattresses were quite comfy. We enjoyed cooking and hanging out in the living area. "
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
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (22)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AED 316
AED 901 total
includes taxes & fees
19 May - 20 May
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, (98)
"We had a great stay here in December. Communication was great and the property owner was very nice and helpful! Would definitely recommend this location. We will definitely return on our next trip if it’s available. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Dramatic, Spacious Wrigley Loft + Private Rooftop, Grill - Ranked GUEST FAVORITE
Smart TV, fireplace, DVD player, foosball

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

10.0 out of 10, Exceptional, (87)
"Had a great stay, close to train, close to great food! Wonderful host!"
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, (82)
"Would definitely stay again!"
The price is AED 415
AED 857 total
includes taxes & fees
27 May - 28 May
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, (60)
"Fantastic location in Old Town. Very spacious rental, check-in was easy, would definitely stay again and recommend!! "
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

9.4 out of 10, Exceptional, (3)
"We had a very nice time with no issues! We would absolutely stay here again."
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.
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Other property types in Westchester

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (753)
"we enjoyed the stay"
The price is AED 465
AED 654 total
includes taxes & fees
27 May - 28 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (506)
"Great stay "
The price is AED 409
AED 480 total
includes taxes & fees
27 May - 28 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (281)
"Cool location"
The price is AED 461
AED 541 total
includes taxes & fees
27 May - 28 May
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 4980 lodging choices including 2435 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.