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Featured Cottages in Far Southwest Side

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Stroll through a charming neighborhood with a mix of two-story and single-story homes, each with its own unique character.

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Cozy Westmont Home: Walk to Metra Station!
Relax in a cozy Adirondack chair arrangement around a fire pit on this outdoor deck.

Cozy Westmont Home: Walk to Metra Station!

3.0 star property
2.0 out of 10, (1)
"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...
Cozy Westmont Home: Walk to Metra Station!
4 Mi to Lake Michigan: East Chicago Home w/ Grill
Residential property with a brick building and a side extension, set amidst a grassy yard with a paved driveway.

4 Mi to Lake Michigan: East Chicago Home w/ Grill

3.0 star property
4 Mi to Lake Michigan: East Chicago Home w/ Grill
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Interior

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Front of property

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So cozy. Feels like staying in a guest house with the whole place to yourself! "
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Stunning two-story home with a garage, front entrance, and beautifully manicured yard.

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

3.0 star property
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Set amidst a serene yard with a large tree and a blue fence, this house features a gabled roof and a chimney.

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
3 Mi to Hard Rock Casino: Charming Home in Gary!
Interior

3 Mi to Hard Rock Casino: Charming Home in Gary!

3.0 star property
3 Mi to Hard Rock Casino: Charming Home in Gary!
Gary Vacation Rental ~ 5 Mi to Lake Michigan!
Stunning two-story house with a central entrance, flanked by windows and a small chimney.

Gary Vacation Rental ~ 5 Mi to Lake Michigan!

3.0 star property
Gary Vacation Rental ~ 5 Mi to Lake Michigan!
Spacious Family Glenwood Estates Home w/ Hot Tub!
Interior

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
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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Top Far Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Clean. Friendly staff. Great Location"
Wendy 1-night trip
Posted 13 hours ago
InterContinental Chicago Magnificent Mile by IHG