Search Apartments in Crestwood

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Crestwood apartments

TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"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 AED 415
AED 848 total
includes taxes & fees
9 Mar - 10 Mar
Sun-Drenched 1BR Apartment
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AED 716
AED 1,657 total
includes taxes & fees
18 Mar - 19 Mar
River North Rooftop With In and Out Parking 3
TV, offices

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (22 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
United States
Cassidy L.
The price is AED 317
AED 1,357 total
includes taxes & fees
8 Mar - 9 Mar
3BR Luxury Suite w/Gym and Balcony
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AED 415
AED 848 total
includes taxes & fees
10 Mar - 11 Mar
Modern Comfort: 1BR Unit w/ Laundry
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is AED 415
AED 806 total
includes taxes & fees
8 Mar - 9 Mar
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AED 415
AED 852 total
includes taxes & fees
8 Mar - 9 Mar
West Loop Living – Bright 1BR
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 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AED 415
AED 848 total
includes taxes & fees
10 Mar - 11 Mar
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
Chicago-Themed 1BR in a Central Spot near Downtown
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is AED 2,567
AED 4,487 total
includes taxes & fees
11 Mar - 12 Mar
Spacious 4BR Central Apartment w/ Skyline Views
Interior

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

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is AED 506
AED 1,079 total
includes taxes & fees
8 Mar - 9 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very Good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is AED 397
AED 913 total
includes taxes & fees
8 Mar - 9 Mar
Your Perfect 2BR Home
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very Good, (32 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is AED 327
AED 816 total
includes taxes & fees
16 Mar - 17 Mar
Oak Park Queen
Interior

Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking
Oak Park
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is AED 643
AED 1,425 total
includes taxes & fees
3 Apr - 4 Apr
Spacious, lovely 2bed 1bath with free parking
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is AED 397
AED 1,081 total
includes taxes & fees
17 Mar - 18 Mar
Cozy, Comfortable and Convenient apartment. Close to everything!
2 bedrooms, iron/ironing board, travel crib, WiFi

2BR Cozy & Functional Unit

2BR Cozy & Functional Unit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
2BR Cozy & Functional Unit
Terrace/patio

Chicago 2BR, Private Deck w/ Fire Pit, and Free Street Parking

Chicago 2BR, Private Deck w/ Fire Pit, and Free Street Parking
West Town
10.0 out of 10, Exceptional, (2 reviews)
"I wish I could give this place more stars. The host was very welcoming and responsive. The property was clean and very welcoming. I would recommend anyone to stay at this location. Very good hosts "
United States
Alexander O.
Chicago 2BR, Private Deck w/ Fire Pit, and Free Street Parking
TV

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (1 review)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
The price is AED 290
AED 992 total
includes taxes & fees
16 Mar - 17 Mar
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Interior

King Studio. Free Breakfast. Indoor Pool. Gym.

King Studio. Free Breakfast. Indoor Pool. Gym.
Schererville
The price is AED 477
AED 616 total
includes taxes & fees
8 Mar - 9 Mar
King Studio. Free Breakfast. Indoor Pool. Gym.
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crestwood Hotel Reviews

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent
"Yes"
Vickie 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Chicago - Magnificent Mile

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 5640 lodging choices including 1640 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's a favorite apartment for my stay in Crestwood?
Below are some of the more popular apartments in the area to choose from: Urban Farm Fun with Goats 10 Minutes To Downtown!: Located in Chicago, 15.8 mi/25.5 km from the heart of Crestwood. Includes Smart TVs. Access to onsite laundry facilities is available on site. 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place: Located 15.3 mi/24.5 km away in Chicago. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Historic and Unique Brownstone in Gold Coast - 3: 17.9 mi/28.8 km away in Chicago.
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.

Explore a world of travel with Expedia