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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Featured Condo Rentals in Crestwood

NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (167)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Classic Lincoln Park 2 bedroom condo- parking included
Outdoor dining

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (70)
"We had a great stay at the rental. Stacy was an amazing host. We would definitely stay there again. "
Classic Lincoln Park 2 bedroom condo- parking included
Guild #1 | Gold Coast Mag Mile Best Location
Interior

Guild #1 | Gold Coast Mag Mile Best Location

9.8 out of 10, Exceptional, (46)
"My friend and our kids rented this place for a long weekend in Chicago. The property is great, in a fabulous location, and the owners are so kind and easy to get in touch with."
Guild #1 | Gold Coast Mag Mile Best Location
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
Smart TV, books

MICH AVE #23 2bd/2ba Downtown, Museums w/ Views

10.0 out of 10, Exceptional, (17)
"We thoroughly enjoyed our stay here. The condo was clean, the beds were comfortable and everything we needed was available. The owners were very communicative, friendly and helpful. The view was amazing, especially at sunset. "
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
Entire 2 bedroom with Office & Deck!
Property grounds

Entire 2 bedroom with Office & Deck!

9.2 out of 10, Wonderful, (11)
"Good stay"
Entire 2 bedroom with Office & Deck!
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Fridge, microwave, oven, stovetop

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

9.0 out of 10, Wonderful, (29)
"It was nice"
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Gorgeous 3BR River North Condo - Free Parking
Fridge, microwave, oven, stovetop

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (18)
"This spacious condo was perfect for our family of 7. Having a parking spot was a huge help and the location was incredibly convenient for use of public transport throughout our stay. We'd definitely stay there again!"
Gorgeous 3BR River North Condo - Free Parking
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
Property grounds

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

9.6 out of 10, Exceptional, (26)
"Everything was good and it was in a great location. Renters were kind and frequently checked in. "
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
Downtown Mich Ave #7| Park View Penthouse +gym
Property grounds

Downtown Mich Ave #7| Park View Penthouse +gym

10.0 out of 10, Exceptional, (5)
"Great location...host quick response..."
Downtown Mich Ave #7| Park View Penthouse +gym
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
Smart TV, books

MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba

10.0 out of 10, Exceptional, (24)
"This apartment was perfect for our stay in Chicago. It was close to everything we wanted to see and had access to bunches of restaurants and such within walking distance."
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (183)
"A perfect place to stay. The rooftop bar has the BEST views of the city, especially around sunset. I would definitely stay here again! "
NEW LUXURY PENTHOUSE CONDO
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
TV

Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover

9.6 out of 10, Exceptional, (22)
"The flat was super spacious and very cute! Walkable to everything that you would need. The location is fantastic as far as access to dining and the lakefront I will definitely be saving this one to visit regularly!"
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Exterior

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

7.8 out of 10, Good, (7)
"Needed a spot in Chicago in a pinch, I was able to get it. Street side parking and transportation ease was at my fingertips. Two days of convenience was all that was needed. It was delivered."
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Chicago Condo: Near Lincoln Park & DePaul!
Fridge, microwave, stovetop, coffee/tea maker

Chicago Condo: Near Lincoln Park & DePaul!

9.8 out of 10, Exceptional, (11)
"You can't beat the location, the street is lovely and quiet and close to public transit, Lincoln Park, shopping, etc. The condo is small but well appointed and clean. (There wasn't soap/shampoos so pack accordingly : )). Overall a lovely place in a great location. "
Chicago Condo: Near Lincoln Park & DePaul!
Gorgeous N. Kenwood/Hyde Park
Fridge, microwave, oven, stovetop

Gorgeous N. Kenwood/Hyde Park

2.0 star property
10.0 out of 10, Exceptional, (3)
"We absolutely loved the apartment! It was huge with plenty of room for our two kids and ourselves. The property owner made sure we had a pack and play and bassinet for our youngest which made traveling by plane so much easier. The place was clean and the neighborhood was great. Right near everything we needed without being stuck downtown. Even with street parking we never had to worry about getting a spot close if not right in front of the gate. Check in and check out was a breeze and we weren’t...
Gorgeous N. Kenwood/Hyde Park
Luxuriant, Foodie, Culture,
Property grounds

Luxuriant, Foodie, Culture,

9.2 out of 10, Wonderful, (20)
"Really enjoyed the property!! It was nice and clean and smelled great!!! I would definitely stay here again!! Nice and spacious as well!"
Luxuriant, Foodie, Culture,
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover
Fridge, microwave, oven, dishwasher

Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

9.4 out of 10, Exceptional, (9)
"Our stay was wonderful. We had everything that we needed and more! It was very spacious and clean. "
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Smart TV, books

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

10.0 out of 10, Exceptional, (20)
"Very clean and comfortable experience with very responsive hosts ! Would recommend "
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Smart TV

Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba

10.0 out of 10, Exceptional, (35)
"The property was exactly as described. It’s in a great location close to the museum campus. Bedrooms were spacious with comfortable beds and excellent closet space. Kitchen was well stocked with everything we needed. it was perfect for our trip and we would consider staying again."
Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Bucktown Private Condo
Fridge, microwave, oven, stovetop

Bucktown Private Condo

9.8 out of 10, Exceptional, (9)
"Great location… quiet, safe, with plenty of restaurants in the area. Would definitely recommend."
Bucktown Private Condo
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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Frequently asked questions

What is there to do in Crestwood near my condo?
The most practical travel accessory is a well-planned to-do list. Hollywood Park is a wonderful spot to start your adventures in Crestwood.