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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Apartments in Westchester

4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is SAR 345
SAR 1,126 total
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
West Loop Living – Bright 1BR
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is SAR 297
SAR 773 total
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
Sun-Drenched 1BR Apartment
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is SAR 259
SAR 621 total
includes taxes & fees
1 Jan - 2 January 2026
Gold Coast Living: Modern Studio Unit
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
The One: A 1BR Stay That Feels Like Home
Interior
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is SAR 760
SAR 1,579 total
includes taxes & fees
11 Dec - 12 Dec
Your Chicago get Away
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is SAR 514
SAR 1,345 total
includes taxes & fees
14 Dec - 15 Dec
River North Rooftop With In and Out Parking 1
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is SAR 687
SAR 1,568 total
includes taxes & fees
19 Dec - 20 Dec
South Loop Rooftop With In and Out Parking 3
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
The price is SAR 225
SAR 582 total
includes taxes & fees
9 Dec - 10 Dec
Modern Studio Near UChicago
Living area
Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6

2.0 star property
Downtown Chicago
The price is SAR 608
SAR 1,477 total
includes taxes & fees
22 Dec - 23 Dec
Downtown Chicago Stay with Free In & Out Parking 6
TV, offices
Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is SAR 488
SAR 1,314 total
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is SAR 236
SAR 632 total
includes taxes & fees
4 Jan - 5 January 2026
Sleek 1BR Apt w/ Laundry
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is SAR 570
SAR 1,424 total
includes taxes & fees
18 Dec - 19 Dec
Modern West Loop Gem-City Views & Prime Location 3
Fridge, microwave, oven, stovetop
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is SAR 225
SAR 771 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Downtown Chicago
The price is SAR 236
SAR 632 total
includes taxes & fees
1 Jan - 2 January 2026
Complete 1BR Home Sum
Interior
Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment

Hyde Park
9.0 out of 10, Wonderful, (6)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
The price is SAR 225
SAR 619 total
includes taxes & fees
9 Dec - 10 Dec
Chic Retreat: Cozy 1BR Apartment
TV, offices
Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago

Hyde Park
10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is SAR 225
SAR 619 total
includes taxes & fees
10 Dec - 11 Dec
Bright & Cozy 1BR Near UChicago
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"What a fantastic hotel. The staff were absolutely lovely, so friendly and helpful. We had breakfast there each morning and it was delicious, so much choice. The communal areas were relaxed, vibrant and comfortable. Our room was very comfortable and provided everything we needed. Location was brilliant everything was on our doorstep "
priscilla jane norwood 3-night trip
Posted 7 hours ago
citizenM Chicago Downtown

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 5567 lodging choices including 1713 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.