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Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Southwest Side vacation rentals

A living room with a grey sofa, two chairs, a coffee table, and a small side table.

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
$223 nightly
The price is $249
Nov 10 - Nov 11
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A living room with a sectional sofa, two armchairs, a coffee table, and artwork on the walls.

2. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
$312 nightly
The price is $383
Nov 2 - Nov 3
Total with taxes and fees
Spacious Apt | 4 Queen Beds | Free Parking
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

3. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (22 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,398 reviews)
"10/10 2nd time staying here!"
United States
Rosa
$135 nightly
The price is $159
Nov 22 - Nov 23
Total with taxes and fees
Sentral Michigan Avenue
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (80 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
$229 nightly
The price is $272
Nov 2 - Nov 3
Total with taxes and fees
Kasa Lake Shore Chicago
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

6. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
$137 nightly
The price is $151
Nov 12 - Nov 13
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a blue sofa, a patterned rug, and a television.

7. 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.
$181 nightly
The price is $202
Nov 10 - Nov 11
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A table with a book titled "MANIFEST & EXECUTE," a cup of coffee, a bowl of raspberries, a small potted plant, and a vase with white flowers.

8. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
2BR Fitness Pad • Private Gym • Sleeps 7
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. 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.
$206 nightly
The price is $248
Nov 2 - Nov 3
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

10. 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.
$217 nightly
The price is $256
Nov 2 - Nov 3
Total with taxes and fees
Private Workspace • Sleeps 4 • Modern and Stylish
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

11. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (72 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
$206 nightly
The price is $212
Nov 8 - Nov 9
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a tiled backsplash.

12. 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, (74 reviews)
"Easy access to the Green Line."
United States
Michael
$196 nightly
The price is $224
Nov 10 - Nov 11
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

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.
$294 nightly
The price is $353
Nov 8 - Nov 9
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

14. 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
$297 nightly
The price is $367
Nov 2 - Nov 3
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

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
$226 nightly
The price is $247
Nov 9 - Nov 10
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

16. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (49 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
$138 nightly
The price is $162
Nov 2 - Nov 3
Total with taxes and fees
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

17. 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.
$108 nightly
The price is $133
Nov 2 - Nov 3
Total with taxes and fees
Cozy studio in Andersonville Chicago
A modern living room with a sofa, a TV, and a dining area with stools.

18. 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, (24 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
$203 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A modern building with a brick facade, large windows, and a central entrance area.

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.
$213 nightly
The price is $243
Nov 2 - Nov 3
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

20. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
$236 nightly
The price is $270
Nov 2 - Nov 3
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
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

Arlo Chicago

Arlo Chicago

10/10 Excellent
"Excellent location! Friendly and helpful staff :-) Get rid of the urban fee—nickel and dimming customers. That was a Covid tax—not happy about paying for internet"
Michael 3-night trip
Posted less than an hour ago
Arlo Chicago

Find out more about Southwest Side

Everything you need to know about Southwest Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southwest Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southwest Side rentals

At Expedia, we put the best Southwest Side vacation 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 vacation.

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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