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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 1484 Apartments in Crestwood with updated reviews, rates, and availability.

1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (125)
"One of the best VRBOs I’ve been in! "
1F Chicago's Little italy Graystone nearDowntown
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (32)
"I didn’t realize when I booked this unit that I would have to carry my luggage up two flight of stairs. Unit is spacious, bathroom is a little tight the only issue I experienced was NOISE, first two nights it was the heater (I think) the last night I could hear foot steps from above and on the early morning of Monday it sounded like construction. Location is great if you want to be steps from high end shopping and restaurants. "
Chic & Historic Apartment Steps from Mag Mile
Remodeled West Loop Apartment Near United Center
Interior

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
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Point of interest

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (223)
"I’ve stayed at this host’s properties several times, and the places are all lovely and welcoming with lots of extra touches and conveniences!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Fridge, microwave, oven, stovetop

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (103)
"It was exactly as expected. Clean and easy check in and check out well supplied!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Luxurious HUGE Penthouse with 4000+ Games, Arcades
Smart TV, video games, foosball, books

Luxurious HUGE Penthouse with 4000+ Games, Arcades

10.0 out of 10, Exceptional, (1)
"The spot was wonderfuke management was responsive. The space was big and comfortable. Games were available. We did have to deal with missing players ok fusball table and pool may need new accessories but we still enjoyed our time there overall i would recomended. When i advised management of fusball table thry offered to send someone, so props to their respokse time."
Luxurious HUGE Penthouse with 4000+ Games, Arcades
Clarendon Hills Garden
Exterior

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
Cozy Apartment in Lincoln Park
Interior

Cozy Apartment in Lincoln Park

Cozy Apartment in Lincoln Park
Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN
Fridge, microwave, oven, stovetop

Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN

9.8 out of 10, Exceptional, (17)
"Host was very communicative, we were going to a convention(bunch of nerds) which meant we got up around 7, returned about midnight. Parking on the street has restrictions during the weekday(host explained them right away). Yep ... Great stay!"
Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN
Luxury Loft Collection 02 - Terrace - River North
TV, stereo, offices

Luxury Loft Collection 02 - Terrace - River North

10.0 out of 10, Exceptional, (14)
"This lot was a perfect spot to visit Chicago! The loft was beautiful and well kept and the location was perfect for our group. Everything was clean and very comfortable. We would definitely rent this property again!!"
Luxury Loft Collection 02 - Terrace - River North
Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover
Interior

Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover

8.8 out of 10, Excellent, (6)
"Getting into the townhome was horrible . Code to open the gate was not working and also the key to get into the back door didn’t work. It took over an hour for someone to come let us into the unit. No Toilet paper, battery low in the firearm. Alarmed beeped all night. Sink in the basement bathroom was plugged up . "
Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover
Cozy modern unit w/ easy access to downtown Chi
Exterior detail

Cozy modern unit w/ easy access to downtown Chi

9.4 out of 10, Exceptional, (38)
"Wesley was super easy to work with. The area is great; the space is great; no complaints at all.Thanks again!"
Cozy modern unit w/ easy access to downtown Chi
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (55)
"Quiet, fun place to stay. The apartment was clean, and exactly what we were looking for. Didn't see a single neighbor during our stay. There are a lot of stairs, just in case you overpack and have a gigantic suitcase. The beds were comfortable. One of the queen bedrooms does not have exterior windows, there's a window above the door, but that just made it the quietest room in the place. Very cute, we'll be back!"
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Beautiful Downtown 3BR with Free Parking
Smart TV, fireplace

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
Historic Oak Park Residence
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge

Historic Oak Park Residence

2.0 star property
9.6 out of 10, Exceptional, (7)
"A little difficult to find the driveway in the dark, but otherwise great. "
Historic Oak Park Residence
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Point of interest

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

9.6 out of 10, Exceptional, (77)
"Great place, great location!"
The price is AED 367
AED 779 total
includes taxes & fees
10 Mar - 11 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Chic Euro City Getaway- Close to Downtown
Smart TV

Chic Euro City Getaway- Close to Downtown

9.8 out of 10, Exceptional, (6)
"We absolutely loved the property!!! It had everything we needed and within a short drive from downtown. The host is super friendly and responsive. Overall, the best spot you will find in Chicago!!!"
Chic Euro City Getaway- Close to Downtown
Chic 2-bedroom in center of Lincoln Park/Depaul/Wrigley + Parking
Fridge, microwave, oven, stovetop

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
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (689)
"it was alright, $77 extra for parking, no breakfast included but it was like a little apartment. no fan for guests either. no phone for communication but u can text their number yet they take forever to respond. "
The price is AED 465
AED 654 total
includes taxes & fees
9 Mar - 10 Mar
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (442)
"Loved the app and process for checking-in and out. The property itself could use some TLC, there were lots of scuff marks and scratches in the walls due to prior tenants. Our unit could have used a painting. There also wasn't a space to get extra toiletries per the app, would take this out if it's not really an option. "
The price is AED 336
AED 394 total
includes taxes & fees
27 Mar - 28 Mar
Sonder South Wabash
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AED 493
AED 578 total
includes taxes & fees
5 Mar - 6 Mar
Found Chicago powered by Sonder
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 5054 lodging choices including 2558 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 top apartments in the area to choose from: Near Oak Park with all the comforts of home. 10 min ride to downtown Chicago: Located 14.8 mi/23.8 km away in Chicago. Free WiFi, separate dining areas, and Smart TVs are included. 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place: It’s situated in Chicago, 15.3 mi/24.5 km away. Includes free WiFi and Smart TVs. Remodeled West Loop Apartment Near United Center: Located 15.3 mi/24.7 km away in Chicago. Free WiFi, private balconies, and fireplaces are included. Access to a rooftop terrace is available on site. Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC: It’s located in Chicago, 15.1 mi/24.3 km from Crestwood. Includes free WiFi and Smart TVs.
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.