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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
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Browse Select Southwest Side Cottages

“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)
"The property was much bigger than we expected to it, the back and front patio were wonderful."
“The cottage” 2 bedrooms cozy and private home
Des Plaines Vacation Rental w/ Spacious Backyard!
House (3 Bedrooms) | Interior

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
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!
2 Mi to Northwestern: Updated Home w/ Game Room!
House (3 Bedrooms) | 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!
Cozy Westmont Home: Walk to Metra Station!
House (2 Bedrooms) | Front of property

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
House (3 Bedrooms) | 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!
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Nice and very clean. Friendly and helpful staff. Very close to bus stop (bus 20) takes you to Magnificent Mile, The Bean…and bus 8 took us right to Rate field for a White Sox game. Just blocks down from Randolph Ave… lots of fun outdoor eateries!! Only recommendation- don’t take a room next to elevator because you’ll hear it go up and down ALL night long."
Betty 3-night trip
Posted 8 hours ago
Crowne Plaza Chicago West Loop by IHG