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1 Aug - 3 Aug
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Featured Cottages in Southwest Side and around

Des Plaines Vacation Rental w/ Spacious Backyard!
Outdoor dining

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
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!
“The cottage” 2 bedrooms cozy and private home
Property grounds

“The cottage” 2 bedrooms cozy and private home

9.4 out of 10, Exceptional, (8)
"We were at this location for 13 days while visiting family. It was just what we needed for our stay. Clean and functional, enough amenities for a long stay "
“The cottage” 2 bedrooms cozy and private home
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!
2 Mi to Northwestern: Updated Home w/ Game Room!
Interior

2 Mi to Northwestern: Updated Home w/ Game Room!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This recently remodeled home was perfect for our family trip. It was immaculate, comfortable, spacious and well appointed. "
2 Mi to Northwestern: Updated Home w/ Game Room!
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
Exterior

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

3.0 star property
Home w/ Yard & Patio ~ 30 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!
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 Southwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"The hotel was great,the staff were friendly and the area felt safe. Had lots of fun. Thanks. Highly recommended "
Anonymous traveller 3-night trip
Posted 12 hours ago
Embassy Suites by Hilton Chicago Downtown River North