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Jul 11 - Jul 13
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Aug 1 - Aug 3
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Aug 29 - Aug 31

Browse Select Homewood Condo Rentals

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

8.0 out of 10, Very good, (8)
"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
Gorgeous N. Kenwood/Hyde Park
Fridge, microwave, oven, stovetop

Gorgeous N. Kenwood/Hyde Park

2.0 star property
9.6 out of 10, Exceptional, (5)
"Unit was very nice and spacious. Communication with owner throughout my stay was excellent. I will definitely consider this unit again my next trip to Chicago."
Gorgeous N. Kenwood/Hyde Park
Chic 2-bedroom Condo near McCormick Pl with Parking Spot
Fridge, microwave, oven, stovetop

Chic 2-bedroom Condo near McCormick Pl with Parking Spot

10.0 out of 10, Exceptional, (1)
"Perfect apartment to go to the convention center, our walk to the event was closer than our friends who stayed in the Marriott and walked via the bridges. "
Chic 2-bedroom Condo near McCormick Pl with Parking Spot
Bronzeville Manor walking distance to hospitals
Interior

Bronzeville Manor walking distance to hospitals

10.0 out of 10, Exceptional, (15)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
Terrace/patio

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

7.0 out of 10, Good, (4)
"We stayed for 4 days for the ACDC concert. It was a cute little place. People all around were friendly. A big suggestion when you arrive. Go to the side door not the front door. We had a very friendly maintenance man named Berto! Only a few issues to note. The pillows were terrible! Not alot around to walk to but there was a few grocery stores. "
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
Luxury Stay on UChicago Campus 11 min walk to hospitals
Exterior

Luxury Stay on UChicago Campus 11 min walk to hospitals

10.0 out of 10, Exceptional, (5)
"Our family stay was wonderful! The property was great, the owners were available and courteous. "
Luxury Stay on UChicago Campus 11 min walk to hospitals
Lovely 2 Bedroom Condo With Pool
Exterior

Lovely 2 Bedroom Condo With Pool

Lovely 2 Bedroom Condo With Pool
The Chic Urban Oasis Near the Lake!
Beach

The Chic Urban Oasis Near the Lake!

7.6 out of 10, Good, (4)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
1-bedroom condo next to Chicago Midway International Airport
Fridge, microwave, oven, stovetop

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (4)
"super nice place!"
1-bedroom condo next to Chicago Midway International Airport
4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Fridge, microwave, oven, stovetop

4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (12)
"Everything was as advertised and super convenient for our group if 8. Highly recommended VRBO! "
4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

8.8 out of 10, Excellent, (11)
"Great place!"
Modern Condo-Obama & University of Chicago Area
A luxury vintage condo close to lakefront and minutes from downtown!
Fridge, microwave, oven, stovetop

A luxury vintage condo close to lakefront and minutes from downtown!

A luxury vintage condo close to lakefront and minutes from downtown!
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Property grounds

♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!

10.0 out of 10, Exceptional, (17)
"Loved our stay! The property was beautiful, with comfortable furnishings that made us feel right at home. Everything was clean and well-maintained. We’ll definitely rent again!"
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Spacious two bedroom condo with a cozy feel!
Interior

Spacious two bedroom condo with a cozy feel!

8.4 out of 10, Very good, (5)
"Very nice amenities. Comfortable beds."
Spacious two bedroom condo with a cozy feel!
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Fridge, microwave, oven, stovetop

Spacious 2 bedroom 2 bath 10 Minutes to Down Town

9.8 out of 10, Exceptional, (19)
"Awesome place"
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Gorgeous Parisian Retreat on University of Chicago Campus
Interior

Gorgeous Parisian Retreat on University of Chicago Campus

Gorgeous Parisian Retreat on University of Chicago Campus
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Fridge, microwave, oven, stovetop

The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!

9.0 out of 10, Wonderful, (6)
"Rough start getting into the place but once we got over anything we needed i would use this place again"
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Wonderful Three Bedroom Condo in Woodlawn
Private kitchen

Wonderful Three Bedroom Condo in Woodlawn

Wonderful Three Bedroom Condo in Woodlawn
420 zen environment surrounded by boho chic decor~Luv Happii House.
Fridge, microwave, oven, stovetop

420 zen environment surrounded by boho chic decor~Luv Happii House.

10.0 out of 10, Exceptional, (2)
"Very clean and cute inside. Smelt AMAZING. Not a bad location and the area was quiet."
420 zen environment surrounded by boho chic decor~Luv Happii House.
Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private parking
Fridge, microwave, oven, stovetop

Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private parking

Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private 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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Frequently asked questions

Why book your condo in Homewood with Expedia?
Booking a condo in Homewood is as easy as clicking on your travel dates and choosing an option that meets your requirements. Looking for something budget friendly or upmarket, or a stay that also features a pool and free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect pad.
How can I find cheap condos in Homewood?
Expedia can help you easily locate cheap condos in Homewood. To lock in your special stay in a few quick clicks, simply use the filter tool to refine your search results by budget, star rating and amenities.
What is there to do in Homewood near my condo?
If you'd like to discover the best of Homewood, make tracks to Ravisloe Country Club. It's a hit with locals and travelers alike.