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Far 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 Far Southwest Side vacation rentals

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

1. 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
$160 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
$211 nightly
The price is $251
Nov 4 - Nov 5
Total with taxes and fees
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,393 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 blue sofa, a patterned rug, and a television.

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.
$192 nightly
The price is $215
Nov 10 - Nov 11
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

5. 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
$195 nightly
The price is $223
Nov 11 - Nov 12
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

6. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
$232 nightly
The price is $274
Nov 5 - Nov 6
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

7. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
$640 nightly
The price is $711
Nov 9 - Nov 10
Total with taxes and fees
Vibrant House, Walk to Train, Game Room
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.
$256 nightly
The price is $303
Nov 1 - Nov 2
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
A neatly made bed with a black headboard, two fluffy pillows, and a stack of towels.

9. Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
$236 nightly
The price is $263
Nov 10 - Nov 11
Total with taxes and fees
Bright & Spacious 2BR– Prime Hyde Park Location
A rooftop terrace with a brick wall, large windows, and a metal railing.

10. 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.
$226 nightly
The price is $272
Nov 1 - Nov 2
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

11. 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.
$151 nightly
The price is $186
Nov 2 - Nov 3
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A wooden deck with a railing, a staircase, and a window with a wreath.

12. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (36 reviews)
"I had a fun stay "
United States
Jusu K.
$184 nightly
The price is $206
Nov 1 - Nov 2
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

13. 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.
$260 nightly
The price is $298
Nov 2 - Nov 3
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

14. 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
$205 nightly
The price is $211
Nov 5 - Nov 6
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern building with a brick facade, large windows, and a central entrance area.

15. 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.
$234 nightly
The price is $268
Nov 3 - Nov 4
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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.

16. 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
$308 nightly
The price is $380
Nov 1 - Nov 2
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A rooftop terrace with a brick wall, large windows, and a metal railing.

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

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.4 out of 10, Exceptional, (31 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
$223 nightly
The price is $268
Nov 4 - Nov 5
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Private kitchen

18. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (5 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveler
$497 nightly
The price is $613
Nov 2 - Nov 3
Total with taxes and fees
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A modern bedroom with a bed, a sofa, and a hanging plant.

19. 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.
$113 nightly
The price is $139
Nov 3 - Nov 4
Total with taxes and fees
Cozy studio in Andersonville Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

20. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (48 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
$165 nightly
The price is $194
Nov 2 - Nov 3
Total with taxes and fees
Wrigleyville Suites
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 Far Southwest Side Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Excelente hotel, con vista maravillosa y súper céntrico"
Estefany 6-night trip
Posted less than an hour ago
LondonHouse Chicago, Curio Collection by Hilton

Find out more about Far Southwest Side

Everything you need to know about Far 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 Far 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 Far Southwest Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Far Southwest Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Far 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 Far 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 $139 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 Far Southwest Side rentals

At Expedia, we put the best Far 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 Far 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 Far 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 Far 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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