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Check prices for these dates

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25 Jul - 27 Jul
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1 Aug - 3 Aug
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15 Aug - 17 Aug
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12 Sept - 14 Sept

Browse Select Far Southwest Side Cottages

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
House (3 Bedrooms) | Interior

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!
Interior

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
Interior

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!
House (4 Bedrooms) | 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!
House (3 Bedrooms) | 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
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
House (3 Bedrooms) | Interior

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!
House (3 Bedrooms) | 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!
Exterior

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!
House (4 Bedrooms) | 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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Roomy suites, excellent breakfast, friendly staff, walking distance to shopping and sites. Lots of restaurant options as well. "
Tracy Van 2-night trip
Posted 9 hours ago
Embassy Suites by Hilton Chicago Downtown River North