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Our top choices for Southwest Side holiday rentals

1. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is £291
includes taxes & fees
16 Nov - 17 Nov
Spacious Apt | 4 Queen Beds | Free Parking

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (92 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is £176
includes taxes & fees
25 Nov - 26 Nov
Kasa Lake Shore Chicago

3. 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 £120
includes taxes & fees
15 Nov - 16 Nov
Hyde Park Trendy Studio Apartment in Good Spot

4. 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 £150
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is £104
includes taxes & fees
8 Dec - 9 Dec
Wrigleyville Suites

6. 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 £319
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking

7. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
"Great for extended stays."
United States
Jeff
The price is £169
includes taxes & fees
6 Dec - 7 Dec
Sentral Michigan Avenue

8. 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 £166
includes taxes & fees
16 Nov - 17 Nov
3BR Complete and Spacious Apartment in Ideal Spot

9. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is £169
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town

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 £162
includes taxes & fees
1 Dec - 2 Dec
Chic Suite/Mins to L Train /Laundry/Free Parking

11. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

12. 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.
Private Workspace • Sleeps 4 • Modern and Stylish

13. 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 £200
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

14. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is £131
includes taxes & fees
15 Nov - 16 Nov
Flexhome Wicker Park • Stylish 2BR • Sleeps 6

15. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is £99
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago

16. 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 £135
includes taxes & fees
17 Nov - 18 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

17. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is £279
includes taxes & fees
15 Nov - 16 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

18. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is £200
includes taxes & fees
17 Nov - 18 Nov
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

19. 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 £178
includes taxes & fees
7 Dec - 8 Dec
Chic Studio in the Heart of the Gold Coast

20. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (14 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is £122
includes taxes & fees
17 Nov - 18 Nov
1BR/1BA City Comfort
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

Everything you need to know about Southwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Side holiday rentals we have selected for you start as low as £56 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southwest Side rentals

At Expedia, we put the best Southwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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