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Compare 56 Condo Rentals in Homewood with updated reviews, rates, and availability.

Modern Condo-Obama & University of Chicago Area
Dining

Modern Condo-Obama & University of Chicago Area

9.0 out of 10, Wonderful, (2)
"Nice place. Small, but good for our purposes. Communication with the owner was real easy. "
Modern Condo-Obama & University of Chicago Area
The Chic Urban Oasis Near the Lake!
Interior

The Chic Urban Oasis Near the Lake!

10.0 out of 10, Exceptional, (1)
"Loved the place - stayed for the Air Show and we were close enough to get everywhere quickly!"
The Chic Urban Oasis Near the Lake!
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Bathroom

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

10.0 out of 10, Exceptional, (15)
"Have stayed here multiple times. We always have a good experience. It would have been very helpful to have kitchen towels. I do most of my own cooking & hand wash the dishes."
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Living area

Spacious 2 bedroom 2 bath 10 Minutes to Down Town

9.8 out of 10, Exceptional, (19)
"Loved the split bedroom arrangements. Property clean, kitchen great for cooking and chilling. We had a rainy day… great place to hang out. Neighbors were very kind and helpful."
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
Dining

Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!

10.0 out of 10, Exceptional, (2)
"11 family members in Chicago for a wedding. Enough beds for everyone in the two condos located one above the other. Very convenient."
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Open living room features vaulted ceilings and hardwood floors.

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

10.0 out of 10, Exceptional, (15)
"Our host was amazing. Every question was answered within minutes. The condo itself is fantastic. The massage chair was a great bonus. Wonderful place to stay especially if you are going to the McCormick Convention Center. A five minute drive. Would stay here again. "
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Experience Elegance at Paramount
Living area

Experience Elegance at Paramount

10.0 out of 10, Exceptional, (2)
"Host was super helpful and accommodation was what I needed for a work trip."
Experience Elegance at Paramount
Comfortable Condo in the Heart of Bronzeville by RedAwning
"Furniture","Indoors","Living Room","Table","Home Decor"

Comfortable Condo in the Heart of Bronzeville by RedAwning

5.0 out of 10, (2)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is AED 451
AED 1,546 total
includes taxes & fees
16 Jan - 17 Jan
Comfortable Condo in the Heart of Bronzeville by RedAwning
1-bedroom condo next to Chicago Midway International Airport
Living area

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (1)
"I was very pleased wirh my stay. The unit we stayed in was spacious, clean and had very modern amenities. They host was outstanding! Very prompt in returning any messages. Definitely recommend this property. "
1-bedroom condo next to Chicago Midway International Airport
4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Room

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

9.6 out of 10, Exceptional, (11)
"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
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Interior

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

6.6 out of 10, (4)
"The property was exactly as pictured. Once we mastered the front gate, the rest of the trip was a breeze! It’s an ideal rental for two or three people."
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Spacious two bedroom condo with a cozy feel!
Living Space

Spacious two bedroom condo with a cozy feel!

8.0 out of 10, Very Good, (4)
"Very nice amenities. Comfortable beds."
Spacious two bedroom condo with a cozy feel!
4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Bedroom #1 with full size bed and sofa bed, Roku TV and in-suite bathroom

4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

9.0 out of 10, Wonderful, (11)
"We enjoyed the apartment. It was clean, had enough bath towels and soaps . The beds were comfortable and the bed linens were comfortable. Each bedroom having their own bathroom was a real bonus. the CTA stop was a fairly short walk. Their we re a lot of places to eat that were within walking distance., The kitchen needed more supplies such as dish towels, mixing bowl and spatula. Enjoyed the stay, would stay again if the need arises."
4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Historic Washington-Hyde Park Greystone
Interior

Historic Washington-Hyde Park Greystone

10.0 out of 10, Exceptional, (3)
"The apartment was very nice, well decorated and equipped, thoroughly cleaned and easy to access. Will definitely stay there again if I'm in the area!"
Historic Washington-Hyde Park Greystone
Lovely 2 Bedroom Condo With Pool
Exterior

Lovely 2 Bedroom Condo With Pool

Lovely 2 Bedroom Condo With Pool
420 zen environment surrounded by boho chic decor~Luv Happii House.
Living area

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

10.0 out of 10, Exceptional, (1)
"My stay at the Luv Happy House was the perfect getaway for my birthday. The house looks exactly like it is listed which is so beautiful! I loved everything about this place nd the host was very responsive, even when i called her at 11:00pm because I had a hard time finding the place. She directed me until i got there, I will definitely stay here again."
420 zen environment surrounded by boho chic decor~Luv Happii House.
Trendy apt near McCormick Place & Wintrust Arena
Room

Trendy apt near McCormick Place & Wintrust Arena

6.0 out of 10, (2)
"It met our needs"
Trendy apt near McCormick Place & Wintrust Arena
A luxury vintage condo close to lakefront and minutes from downtown!
Living Room

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

A luxury vintage condo close to lakefront and minutes from downtown!
Luxury Stay on UChicago Campus 11 min walk to hospitals
Living room

Luxury Stay on UChicago Campus 11 min walk to hospitals

10.0 out of 10, Exceptional, (2)
"The condo was excellent. Would definitely rent again. Check in was easy and location great. Thank you. "
Luxury Stay on UChicago Campus 11 min walk to hospitals
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
Living area

Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.

Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage 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 Homewood

Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!
Living area

Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!

9.8 out of 10, Exceptional, (7)
"Clean & Convenient "
Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!
Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE
Interior

Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE

9.6 out of 10, Exceptional, (9)
"House was perfect for myself and coworker for the fabtech event fully stocked kitchen was nice for cooking then hot tub just topped the cake. Very clean place!"
Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE
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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