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Far Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Far Southwest Side vacation rentals

Private kitchen

1. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
$194 nightly
The price is $217
Oct 8 - Oct 9
Total with taxes and fees
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

2. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay "
United States
Harquesha S.
$168 nightly
The price is $179
Oct 13 - Oct 14
Total with taxes and fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (33 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.
$169 nightly
The price is $180
Oct 14 - Oct 15
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
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, (1,350 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
$184 nightly
The price is $216
Oct 26 - Oct 27
Total with taxes and fees
Sentral Michigan Avenue
A rooftop terrace with a brick wall, large windows, and a metal railing.

5. 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, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$213 nightly
The price is $256
Oct 5 - Oct 6
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

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.
$191 nightly
The price is $214
Oct 13 - Oct 14
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

7. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
$271 nightly
The price is $304
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

8. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
$183 nightly
The price is $195
Oct 5 - Oct 6
Total with taxes and fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A modern bedroom with a bed, a sofa, and a hanging plant.

9. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (100 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
$113 nightly
The price is $139
Oct 26 - Oct 27
Total with taxes and fees
Cozy studio in Andersonville Chicago
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

10. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
$229 nightly
The price is $271
Oct 5 - Oct 6
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

11. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (8 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$261 nightly
The price is $309
Oct 5 - Oct 6
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A rooftop terrace with a brick wall, large windows, and a metal railing.

12. 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, (29 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
$213 nightly
The price is $256
Oct 5 - Oct 6
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

13. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
$224 nightly
The price is $247
Oct 5 - Oct 6
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
$216 nightly
The price is $247
Nov 2 - Nov 3
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
Lake

15. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (49 reviews)
"Location is perfect"
United States
Mary
$238 nightly
The price is $283
Nov 4 - Nov 5
Total with taxes and fees
Kasa Lake Shore Chicago
A wooden deck with a railing, a staircase, and a window with a wreath.

16. 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, (35 reviews)
"I had a fun stay "
United States
Jusu K.
$183 nightly
The price is $205
Oct 12 - Oct 13
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

17. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
$440 nightly
The price is $536
Oct 5 - Oct 6
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

18. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"Great stay. Clean place. Happy to come back."
United States
David F.
$103 nightly
The price is $115
Oct 5 - Oct 6
Total with taxes and fees
Beautiful Rustic Cabin for Two!
A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

19. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
$185 nightly
The price is $197
Oct 6 - Oct 7
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

20. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$249 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"I loved my stay here ! i love how close we were to everything, transportation wise . and staff was very friendly and helpful"
Jessica 3-night trip
Posted 6 hours ago
The Chicago Hotel Collection - Magnificent Mile

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 $72 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

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