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Compare 1522 Apartments in Crestwood with updated reviews, rates, and availability.

Sonder Onterie

3.5 star property
9.4 out of 10, Exceptional, (10)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is AED 395
AED 464 total
includes taxes & fees
8 Apr - 9 Apr
Sonder Onterie

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

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

Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

8.8 out of 10, Excellent, (27)
"We are visiting from the United Kingdom and was very happy with this property. Perfect size for our needs, the property was clean and catered with all our needs, the host was very prompt on our requests.Thank you "
Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago

Cozy, Comfortable and Convenient apartment. Close to everything!

9.8 out of 10, Exceptional, (56)
"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 1,005 total
includes taxes & fees
6 Apr - 7 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!

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

10.0 out of 10, Exceptional, (23)
"This was the perfect place to stay for a four day visit to Chicago. The host was super responsive and the apartment is stunning with beautiful original artwork and every convenience you could possibly need. As a frequent Chicago visitor I will definitely rent this space again!"
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

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 441
AED 872 total
includes taxes & fees
15 Apr - 16 Apr
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

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

10.0 out of 10, Exceptional, (56)
"This unit served our family of five well for a few days get away in the city. The hot water went out while we were there but the owner communicated and responded timely. It was a bit dusty, as if it hadn't been occupied in some time, but otherwise it was fine. Can't beat the location and Old Town is awesome."
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

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

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

Cozy 2 Bedroom 1 Bath. Centrally located with shared porch

8.0 out of 10, Very Good, (7)
"If you looking for basic accommodations in an BnB in Chicago, this rental is definitely both. Apartment 2R is cute on the surface. A kitchen, sm. appliances, two bedrooms with LOTS of beds, a decently sized living room, good fridge, safe sleepy neighborhood. SPECIAL NOTE: DO NOT PARK on Archer overnight . YOU WILL BE TOWED. It is quite a long trek to get to the impound lot and at least a 175 fine; it took seven hours off our stay in Chicago. lesson learned the hard wayThe more you look, you...
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch

Beautiful Downtown 3BR with Free Parking

9.4 out of 10, Exceptional, (16)
"Great location with parking! Easy to walk to restaurants/bars. Location location location! "
Beautiful Downtown 3BR with Free Parking

Clean and Comfy Updated Apt in Convenient Location

10.0 out of 10, Exceptional, (19)
"This house is perfect for any visitor. More than enough was available at my fingertips to keep me more than satisfied! Nothing but praises for this property. Walking distance to little nick nacks and what not. Great property, great parking, great area, great owner. 0 Complaints. "
Clean and Comfy Updated Apt in Convenient Location

Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!

9.8 out of 10, Exceptional, (83)
"7 minute walk from Metra, about 15 minutes from downtown Chicago. There is NO hot tub, though. It's listed in the amenities but I asked and the owner was honest in telling me there wasn't one. Great communica"
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!

Clarendon Hills Garden

9.6 out of 10, Exceptional, (5)
"It did the job for me at $100 a night less than the hotel that my seminars were. It is a very old house so don't expect perfection. It was clean and that is what mattered to me."
Clarendon Hills Garden

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (283)
"great price with parking in a GREAT neighborhood. We were not bothered by the music from the bar. that may be worse in the summer, but zero issue for us in March.people we were visiting all could not believe what a great deal it is.The candy jar was a very nice touch. zero problems and the owner (John) was excellent to work with."
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking

2.0 star property
7.6 out of 10, Good, (9)
"Great place overall, location was superb and the place itself was nice. The train from the Armitage stop is super loud though in case that bothers someone. The back rooms behind the second bedroom are so spooky lol but otherwise the place is cute and cozy!"
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking

Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6

10.0 out of 10, Exceptional, (7)
"Wonderful apartment with plenty of space for 3 of us on a work-related trip to Oak Park. Comfortable over a range of temperatures, nice kitchen facilities, excellent laundry, spotlessly clean. Quiet with the windows closed, beautiful deck in the back we used the first (warm) day we were there. Nice one parking space on premise. Only minor issues were top (third) floor location/walk up when toting groceries and TV was a bit difficult to use. Would love to stay there again!"
Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6

4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking

9.4 out of 10, Exceptional, (10)
"Clean, cool sports memorabilia, great location!"
4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking

Luxury Loft Collection 703 - Terrace - River North

2.0 star property
9.8 out of 10, Exceptional, (7)
"We had an amazing stay at this VRBO in Chicago! The location was perfect - right in the heart of everything, making it easy to explore the city. The space itself was exactly what we needed for our group of 8, offering plenty of room for everyone. The floor to ceiling windows provided stunning views, which were an absolute highlight of our stay.A special shout out to the front desk, who provided impeccable service and made us feel at home. The host was also incredibly responsive and...
Luxury Loft Collection 703 - Terrace - River North
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 Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (719)
"I like the view of this place, had a good few of the park and could see Michigan lake in the distance. Pretty cool that it had a wash and dryer, was not expecting that when we came. Like that it’s in walking distance from the museums, made traveling easy. Employees were also very helpful. "
The price is AED 465
AED 654 total
includes taxes & fees
13 Apr - 14 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (463)
"Great!"
The price is AED 404
AED 474 total
includes taxes & fees
6 Apr - 7 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (269)
"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 461
AED 541 total
includes taxes & fees
6 Apr - 7 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 Crestwood?
There are plenty of places to stay with in the larger Chicago area, with 4937 lodging choices including 2461 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?
Here’s a top apartment in the area to consider: Sonder Onterie: Situated in Chicago, 17.5 mi/28.2 km from the heart of Crestwood.
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.