Photo by by Midway Intl Airport

Search Vacation Homes in Southwest Side

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Southwest Side

Vacation Home in Richton Park

2.0 star property
9.0 out of 10, Wonderful, (13)
"Awesome stay!"
United States
Patrick J.
The price is ¥16,867
¥48,620 total
includes taxes & fees
Nov 30 - Dec 1
Spacious 3br home near Chicago, fenced yard for pets

Vacation Home in Robertsdale

2.0 star property
10.0 out of 10, Exceptional, (13)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
The price is ¥22,349
¥31,154 total
includes taxes & fees
Dec 1 - Dec 2
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Vacation Home in Worth

9.6 out of 10, Exceptional, (53)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is ¥24,208
¥51,697 total
includes taxes & fees
Dec 1 - Dec 2
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (12)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is ¥18,976
¥69,820 total
includes taxes & fees
Dec 1 - Dec 2
Vintage Urban Retreat

Vacation Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is ¥10,883
¥43,468 total
includes taxes & fees
Dec 10 - Dec 11
Getaway Near ORD With Great Local Amenities

Vacation Home in Lockport

10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
United States
Rachel
The price is ¥27,332
¥59,346 total
includes taxes & fees
Dec 1 - Dec 2
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Vacation Home in Willow Springs

8.8 out of 10, Excellent, (15)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
The price is ¥28,112
¥62,153 total
includes taxes & fees
Dec 1 - Dec 2
Coziest estate home 20 minutes to downtown

Vacation Home in La Grange Highlands

10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is ¥13,119
¥39,431 total
includes taxes & fees
Dec 1 - Dec 2
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in Belmont Cragin

2.0 star property
The price is ¥14,837
¥85,880 total
includes taxes & fees
Dec 2 - Dec 3
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Maywood

7.8 out of 10, Good, (13)
"Very nice place "
United States
Elliot H.
The price is ¥23,193
¥37,844 total
includes taxes & fees
Nov 30 - Dec 1
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Gary

8.6 out of 10, Excellent, (17)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
The price is ¥25,178
¥69,861 total
includes taxes & fees
Dec 2 - Dec 3
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Vacation Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is ¥26,551
¥48,166 total
includes taxes & fees
Dec 8 - Dec 9
✽ Charming Cottage ✽ close to College/Town/Station

Vacation Home in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is ¥33,173
¥77,033 total
includes taxes & fees
Nov 30 - Dec 1
Enamored in Elmhurst

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ¥25,685
¥78,069 total
includes taxes & fees
Dec 2 - Dec 3
Modern Victorian Vibes ❤️ | Character & Charm

Vacation Home in Wood Dale

10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
The price is ¥27,992
¥61,468 total
includes taxes & fees
Nov 30 - Dec 1
Wonderful in Wood Dale, right by O’Hare airport!

Vacation Home in Homewood

2.0 star property
The price is ¥22,506
¥63,212 total
includes taxes & fees
Nov 30 - Dec 1
Modern Stylish Comfort Near Casino and Hwy

Vacation Home in Burbank

9.4 out of 10, Exceptional, (6)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is ¥28,737
¥72,191 total
includes taxes & fees
Dec 4 - Dec 5
Modern 4BR Retreat Near MDW | LCP Collection

Vacation Home in Forest Park

2.0 star property
The price is ¥22,021
¥64,889 total
includes taxes & fees
Dec 4 - Dec 5
Classic Forest Park Foursquare < 1 Mi to Blue Line

Vacation Home in Skokie

10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
The price is ¥44,871
¥102,344 total
includes taxes & fees
Dec 1 - Dec 2
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Vacation Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
The price is ¥25,301
¥53,131 total
includes taxes & fees
Dec 10 - Dec 11
Cozy Home by O'Hare + EV Plug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Southwest Side Vacation Homes information

Number of reviews
291
Accommodation
346 Vacation Homes
Lowest Price
¥31,154
Highest Price
¥102,344

Explore a world of travel with Expedia