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Compare 1402 Apartments in Crestwood with updated reviews, rates, and availability.

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (119)
"John had the apartment well stocked with coffee, teas, candy, towels, toiletries, and warm robes. Bed were comfy with nice bedding. We would stay here again!! "
1F Chicago's Little italy Graystone nearDowntown

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

10.0 out of 10, Exceptional, (216)
"What a beautiful apartment...and the Christmas decorations were so lovely."
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

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

10.0 out of 10, Exceptional, (267)
"Clean, comfortable and communication was great. Would recommend. "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

9.6 out of 10, Exceptional, (14)
"Host was extremely accomodating. We needed extended early and late check in / out. We worked together to make that happen. Greqt host / perect in and out"
The price is AED 220
AED 365 total
includes taxes & fees
12 Jan - 13 January 2025
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Beautiful Unit CHI in Prime River North - 3

9.8 out of 10, Exceptional, (15)
"Nice place, everything as advertised. Host was very accommodating, we will definitely book again when in area. "
Beautiful Unit CHI in Prime River North - 3

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile

Cozy 2- bedroom w/ patio mins from Midway Airport

9.8 out of 10, Exceptional, (9)
"The owner definitely pays attention to details. It had towels laid out in these cute little baskets a well stocked kitchen in terms of tools and the decor was very charming. The only reason I didn't give 5 stars is because it is an older building so the water pressure in the shower was low, there's no dishwasher and it is a 2 flat and the upstairs unit controlled the heat and we were on the first floor."
Cozy 2- bedroom w/ patio mins from Midway Airport

The Vibe Headquarters

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean and cozy! Home away from home!"
The Vibe Headquarters

Luxury Loft Collection 02 - Terrace - River North

10.0 out of 10, Exceptional, (11)
"We loved our stay. Close to everything. New unit. Plenty of space. Balcony was a bonus! Definitely recommend."
Luxury Loft Collection 02 - Terrace - River North

Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

8.8 out of 10, Excellent, (15)
"Enjoyed our stay, great location, we will stay there again on our next trip to Chicago"
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

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

10.0 out of 10, Exceptional, (102)
"We came to town for a hockey weekend and will absolutely book with them again when we come back. Everything was exactly as pictured or described. Cozy beds, plenty of blankets, pillows, towels, etc. Quiet neighborhood on a beautiful street, and a great location to call home while commuting to and from the rinks. "
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

Lovely 4 Bedroom Spot located in Charming Old Town

10.0 out of 10, Exceptional, (23)
"The apartment was AMAZING! Even better than the photos. All the furnishings were of the finest quality, including the bed linens and towels. The mattresses were exceptionally comfortable. The kitchen was also well stocked with every type of culinary tool, plenty of glasses of every variety. We were a family of 13 and we had plenty of room. The bean bag chairs were a big hit for all ages. We loved the neighborhood. We have some members with food allergies and there were several places they...
Lovely 4 Bedroom Spot located in Charming Old Town

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

Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

10.0 out of 10, Exceptional, (2)
"Great amenities, beautiful views, and very clean. Parking included. "
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

Charming 2-bedroom apartment in Oak Park with WiFi access

10.0 out of 10, Exceptional, (1)
"Very nice place! The only thing i didn't like was the lack of curtains on the dining room windows. "
Charming 2-bedroom apartment in Oak Park with WiFi access

Lux Loop Retreat: Amazing Views, Free Parking

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved this property. It's a corner unit and very private. And quiet. The views during the day are very nice...but at night with all the lights of the city...spectacular! Did I mention the garage is heated? This property is highly recommended. We hope to stay there again someday!"
Lux Loop Retreat: Amazing Views, Free Parking

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (72)
"This is the 3rd time I’ve booked this Ukrainian Village apartment. It’s comfortable and has everything needed for visits into the city. "
Stay in “STYLE” Apartment, close to CHI downtown

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
The price is AED 493
AED 903 total
includes taxes & fees
9 Jan - 10 January 2025
Historic Oak Park Residence

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

9.6 out of 10, Exceptional, (73)
"The home was charming and modest. The apartment was very spacious and quiet, which we loved. Check in and check out was a very easy process and all of the home's instructions, including parking, were easy to understand and follow. The host was super responsive and very friendly. Also, the neighborhood is amazing! "
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Entire Below Level Studio w/ Private Sauna

10.0 out of 10, Exceptional, (28)
"this apartment was super comfy and was super convenient; it made my trip super easy"
Entire Below Level Studio w/ Private Sauna
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, (629)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AED 403
AED 581 total
includes taxes & fees
29 Dec - 30 Dec
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"Great stay "
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is AED 456
AED 535 total
includes taxes & fees
15 Jan - 16 January 2025
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 4905 lodging choices including 2431 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: 1F Chicago’s Little italy Graystone nearDowntown: It’s situated in Chicago, 15.3 mi/24.6 km away. Includes free WiFi and Smart TVs. Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place: 15.3 mi/24.5 km away in Chicago. Free WiFi and Smart TVs are included.
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.