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Compare 1302 Apartments in Crestwood with updated reviews, rates, and availability.

1F Chicago's Little italy Graystone nearDowntown
Enjoy the Linden trees from the sunny bay window.
1F Chicago's Little italy Graystone nearDowntown
10.0 out of 10, Exceptional, (118)
"Great location walking distance of restaurants and some nightlife. Good neighborhood very safe college kids walking the streets not occasion. Are you really lazy lots of amenities more than usual in places like this and enjoyed our state would stay there again"
1F Chicago's Little italy Graystone nearDowntown
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Open Concept Living Room
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (211)
"Enough room for 2 kids and parents qith room to spare"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Clarendon Hills Garden
Room
Clarendon Hills Garden
10.0 out of 10, Exceptional, (2)
"Very clean for being in the basement. Great for the price we got it at! Felt very safe in it's location within a beautiful neighborhood with sidewalks. Walked to the market apx 15 min walk there. There were a TON of LOUD cicadas which was a little eek but I believe that only happens every 17 years? Would of been nice to have a wall separating unit stays instead of just a door. Wasn't sure if someone could come down stairs from the upstairs that wasn't part of our rental. over all though we had a...
The price is AED 184
AED 425 total
includes taxes & fees
23 Nov - 24 Nov
Clarendon Hills Garden
Cozy modern unit w/ easy access to downtown Chi
Living area
Cozy modern unit w/ easy access to downtown Chi
9.4 out of 10, Exceptional, (34)
"Clean, exactly as described and reasonably priced. Also a great location to access public transit & lots of restaurants nearby. Had a great stay!"
Cozy modern unit w/ easy access to downtown Chi
Chic & Historic Apartment Steps from Mag Mile
Living area
Chic & Historic Apartment Steps from Mag Mile
9.8 out of 10, Exceptional, (26)
"Very nice neighborhood, walking distance to Michigan Avenue, great food options, place has everything you need, I’ll stay there again, "
Chic & Historic Apartment Steps from Mag Mile
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Living area
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
9.6 out of 10, Exceptional, (12)
"It was a perfect place for a quick overnight trip."
The price is AED 228
AED 373 total
includes taxes & fees
4 Dec - 5 Dec
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Beautiful Unit CHI in Prime River North - 3
Living Room / Dining Room with Fully stocked kitchen
Beautiful Unit CHI in Prime River North - 3
10.0 out of 10, Exceptional, (13)
"This property is in a great location to many restaurants and bars. There is even a bumping nightclub across the street if that is your scene. It's also large enough to sleep many at a decent price."
Beautiful Unit CHI in Prime River North - 3
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Bright, open-concept living space and kitchen
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
8.0 out of 10, Very Good, (10)
"10 min walk from nearest train station"
Prime Location - Close to Public Transit, Little Italy, the Medical District and UIC by AllSet Turnover
Oak Park Queen
Interior
Oak Park Queen
9.2 out of 10, Wonderful, (9)
"I was mostly confused about how to go about checking in so i had to call. We were told we would get an email soon telling us everything we needed to know which is fine, but we didnt know that till almost check in time. A minor inconvenience but not serious. Loved the area!"
The price is AED 496
AED 950 total
includes taxes & fees
25 Nov - 26 Nov
Oak Park Queen
Sunny Coach House in Historic Oak Park
Living area
Sunny Coach House in Historic Oak Park
9.8 out of 10, Exceptional, (47)
"Hosts were great place check on easy! Would stay again."
Sunny Coach House in Historic Oak Park
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Living room offers comfortable chair, loveseat and a sofa that turns into a bed.
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
9.6 out of 10, Exceptional, (70)
"Booked this place for my family who visited for my wedding. Everything was clean and just as described. The location was super easy to find and instructions were clear. Good location close to Downtown Oak Park and close enough to talk to the train station if needed. Ali was very nice and available via message. Thank you so much!!"
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse B - Sleeps 11
8.8 out of 10, Excellent, (19)
"Grear trip. Great property. Secure building. Very spaciuos. Wish we couldve stayed longer. "
Breathtaking Downtown Penthouse B - Sleeps 11
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Living area
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
9.4 out of 10, Exceptional, (3)
"This rough around the edges property was on par for a budget trip. The neighborhood has a lot of good restaurants within walking distance and it's a short walk to public transportation if you're looking to explore the city. The host was quick to reply to any and all questions/concerns. The only negative would be the living room had animal hair on the rug and couch which stirred up allergies. "
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Luxury Loft Collection 703 - Terrace - River North
Luxury Loft Collection 703 - Terrace - River North
2.0 star property
9.4 out of 10, Exceptional, (3)
"Great location close to public transportation, shopping and restaurants. Very clean and well-equipped, especially with linens and towels. Helpful people working the front door."
Luxury Loft Collection 703 - Terrace - River North
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking
Private kitchen
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking
2.0 star property
7.4 out of 10, Good, (6)
"Affordable, easy to travel around, great communication, and lovely neighborhood. "
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking
The Oak Park Loft
Room
The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at Oak Park. The host was very accommodating,giving us good places to eat. The place was very clean. I'd would go there again."
The price is AED 532
AED 947 total
includes taxes & fees
16 Dec - 17 Dec
The Oak Park Loft
Beautiful Unit CHI in Prime River North - 2
Beautiful Unit CHI in Prime River North - 2
9.0 out of 10, Wonderful, (10)
"Had a great stay, Dan was very responsive. Would stay here again."
Beautiful Unit CHI in Prime River North - 2
Stay in “STYLE” Apartment, close to CHI downtown
Interior
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (69)
"Clean space. Neighborhood felt safe. Beds are super hard though so not ideal for everyone. Also the blinds in the bedrooms don’t block out light very well so be prepared to be up when the sun is up if you stay here"
Stay in “STYLE” Apartment, close to CHI downtown
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
forrestville home
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (66)
"Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay"
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Brownstone, 2 entire units Gold Coast
Living Room with pullout couch (denim colored couch)
Brownstone, 2 entire units Gold Coast
8.8 out of 10, Excellent, (6)
"Overall our experience was positive! The location can't be beat and was what made this such a great college friends reunion (we met almost 20 years ago!). We had 10 women and fit fairly well, though didn't attempt two on the top bunk because the mattress went higher than the railing and the ceiling fan was close. We had a hard time at the beginning getting the air conditioner going, but Dan helped us out and we got it figured out. The kitchens weren't as well-appointed as we expected, but I...
Brownstone, 2 entire units Gold Coast
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
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is AED 396
AED 573 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (208)
"My stay at Sonder was an absolute delight! The property is very clean and the view and vibe was very cozy and perfect! The manager Jess went above and beyond helping out with questions and took great care of me! I will definitely be coming back! "
The price is AED 206
AED 242 total
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AED 443
AED 520 total
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
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 4498 lodging choices including 2136 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?
Listed below are some of the more popular apartments in the area to choose from: Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place: It’s situated in Chicago, 15.3 mi/24.5 km away. Includes free WiFi and Smart TVs. Stay in “STYLE” Apartment, close to CHI downtown: 16.6 mi/26.7 km away in Chicago. Amenities include Smart TVs. Cozy modern unit w/ easy access to downtown Chi: It’s located in Oak Park, 14.9 mi/24 km from Crestwood. Includes free WiFi and private patios.
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.