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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Apartments in Crestwood

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
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
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
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
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
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 342
SAR 1,121 total
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5
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
Stylish 4BR South Loop Home

Stylish 4BR South Loop Home

Greater Grand Crossing
10.0 out of 10, Exceptional, (2)
"Very happy with stay. Good communication from property host. "
United States
Nicole E.
The price is SAR 353
SAR 1,358 total
includes taxes & fees
9 Dec - 10 Dec
Stylish 4BR South Loop Home
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
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
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is SAR 218
SAR 1,260 total
includes taxes & fees
9 Dec - 10 Dec
Spacious 3-bedroom apartment near downtown, FREE PARKING
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
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
Iron/ironing board, travel crib, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago

Hyde Park
10.0 out of 10, Exceptional, (1)
The price is SAR 225
SAR 582 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Charm Studio Apt in Chicago
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave

Hyde Park
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is SAR 236
SAR 693 total
includes taxes & fees
9 Dec - 10 Dec
Explore Hyde Park: 2BR Apt on Blackstone Ave
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 510
SAR 1,336 total
includes taxes & fees
14 Dec - 15 Dec
River North Rooftop With In and Out Parking 1
Interior
Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt

Hyde Park
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is SAR 236
SAR 689 total
includes taxes & fees
9 Dec - 10 Dec
Sleek & Functional 2-Bedroom Apt
Dining
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is SAR 225
SAR 582 total
includes taxes & fees
9 Dec - 10 Dec
Studio Unit | Chic + Prime Location
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 Crestwood Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"the bathroom is so dark"
Audrey 1-night trip
Posted 4 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What's it like to stay at an apartment in Crestwood?
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. Make time to visit the region's favorite sights like Soldier Field.
How do you know if an apartment is the right choice for you?
Offering a kitchen for convenient meals, an apartment usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, but also for families who want the conveniences of home.
What can I expect from the weather during my trip to Crestwood?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Crestwood. 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. Average annual precipitation for Crestwood is 47 inches.
What should I see in Crestwood?
Crestwood is known for its restaurants and shops. Explore the area and cultural attractions such as Moraine Valley Community College Fine and Performing Arts Center, or visit a family-friendly sight such as Hollywood Park. In the larger area, you'll find Soldier Field and Trinity Christian College.
What's the best way to get to and around Crestwood?
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 8.8 mi (14.2 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 23.2 mi (37.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.