Photo by by Midway Intl Airport
Southwest Side Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Southwest Side vacation rentals
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
Rachel
The price is ￥16,529
￥48,118 total
includes taxes & fees
Jun 9 - Jun 10
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
Yiu S.
The price is ￥17,800
￥44,735 total
includes taxes & fees
Jun 15 - Jun 16
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | ArcadeBrighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
Jessica H.
The price is ￥11,586
￥41,667 total
includes taxes & fees
Jun 2 - Jun 3
9.2 out of 10, Wonderful, (1,175 reviews)
"Spacious apartment with stunning view. A great stay!!"
Tina
The price is ￥41,746
￥53,672 total
includes taxes & fees
Jun 14 - Jun 15
9.0 out of 10, Wonderful, (481 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Lissa
The price is ￥49,605
￥62,152 total
includes taxes & fees
May 27 - May 28
3BR Luxury Suite w/Gym and Balcony
3BR Luxury Suite w/Gym and BalconyDowntown Chicago
9.4 out of 10, Exceptional, (28 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
shayna j.
The price is ￥185,789
￥302,022 total
includes taxes & fees
Jun 18 - Jun 19
9.6 out of 10, Exceptional, (193 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
Suyash
The price is ￥28,747
￥46,804 total
includes taxes & fees
May 27 - May 28
River North Rooftop With In and Out Parking 1
River North Rooftop With In and Out Parking 1Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
lucas c.
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Southwest Side Hotel Reviews
Hilton Chicago/Magnificent Mile Suites
8/10 Good
Find out more about Southwest Side
Search for holiday rentals in Southwest Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Southwest Side using one of the methods below:
- View our selection of featured holiday rentals in Southwest Side
- Use the map to find apartments and other holiday homes in the Southwest Side neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Southwest Side while they last
Look no further and take a look at our great range of rental properties in Southwest Side!
Explore a world of travel with Expedia
- Apartments in Southwest Side
- Vacation Homes in Southwest Side
- Condo Rentals in Southwest Side
- Motels in Southwest Side
- Aparthotels in Southwest Side
- B&B in Southwest Side
- Hostels in Southwest Side
- Guest Houses in Southwest Side
- Resorts in Southwest Side
- Cottages in Southwest Side
- Farmstay in Southwest Side
