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Southwest Side Vacation Rentals

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Our top choices for Southwest Side vacation rentals

1. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is CA $89
CA $322 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

2. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is CA $180
CA $517 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Apt | 4 Queen Beds | Free Parking

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,408 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is CA $180
CA $211 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue

4. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is CA $92
CA $213 total
includes taxes & fees
Nov 12 - Nov 13
Hyde Park Trendy Studio Apartment in Good Spot

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (85 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is CA $215
CA $339 total
includes taxes & fees
Nov 22 - Nov 23
Kasa Lake Shore Chicago

6. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is CA $85
CA $261 total
includes taxes & fees
Nov 9 - Nov 10
Great Area Logan Square Apt Games Pets - Sleeps 5

7. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (25 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is CA $99
CA $268 total
includes taxes & fees
Nov 9 - Nov 10
3BR Complete and Spacious Apartment in Ideal Spot

8. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is CA $106
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

9. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is CA $101
CA $249 total
includes taxes & fees
Nov 16 - Nov 17
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

10. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is CA $122
CA $302 total
includes taxes & fees
Nov 17 - Nov 18
Chic Suite/Mins to L Train /Laundry/Free Parking

11. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $106
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

12. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is CA $145
CA $614 total
includes taxes & fees
Nov 11 - Nov 12
Chic Urban Retreat Near Wrigley Field w/Parking

13. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is CA $126
CA $441 total
includes taxes & fees
Nov 21 - Nov 22
Private Workspace • Sleeps 4 • Modern and Stylish

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is CA $243
CA $320 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town

15. Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
The price is CA $100
CA $299 total
includes taxes & fees
Nov 16 - Nov 17
Chic Studio in the Heart of the Gold Coast

16. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (50 reviews)
"Clean room"
United States
Michael
The price is CA $208
CA $244 total
includes taxes & fees
Nov 10 - Nov 11
Wrigleyville Suites

17. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (13 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is CA $93
CA $217 total
includes taxes & fees
Nov 9 - Nov 10
1BR/1BA City Comfort

18. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is CA $219
CA $271 total
includes taxes & fees
Nov 10 - Nov 11
LIVN Millennium Park Downtown Chicago 1 BR

19. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is CA $130
CA $318 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

20. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is CA $140
CA $450 total
includes taxes & fees
Nov 9 - Nov 10
Sleeps 7 • Huge Projector • Designated Workspace
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

Find out more about Southwest Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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