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Far Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Far Southwest Side vacation rentals

A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

1. 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, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is ￥15,217
￥37,321 total
includes taxes & fees
Oct 26 - Oct 27
Chic Suite/Mins to L Train /Laundry/Free Parking
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

2. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is ￥13,116
￥18,230 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Rustic Cabin for Two!
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, (1,375 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥22,629
￥26,564 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

4. 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.
The price is ￥10,087
￥26,104 total
includes taxes & fees
Nov 16 - Nov 17
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

5. 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
The price is ￥17,540
￥40,229 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
A wooden deck with a railing, a staircase, and a window with a wreath.

6. 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)
"Highly recommend this property. It’s located on a quiet clean nice residential street. And the home itself is wonderful: good furnishings, comfortable, three good bedrooms, clean well appointed bathroom, great backyard. I’d stay here anytime I’m in the area."
United States
Ruth Ann G.
The price is ￥22,613
￥32,938 total
includes taxes & fees
Oct 19 - Oct 20
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

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, (23 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 ￥17,382
￥42,011 total
includes taxes & fees
Oct 26 - Oct 27
3BR Complete and Spacious Apartment in Ideal Spot
Private kitchen

8. 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
The price is ￥29,234
￥83,067 total
includes taxes & fees
Nov 2 - Nov 3
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

9. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 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.
The price is ￥8,343
￥45,348 total
includes taxes & fees
Nov 2 - Nov 3
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.

10. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.0 out of 10, Wonderful, (9 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is ￥16,826
￥57,077 total
includes taxes & fees
Oct 28 - Oct 29
Sleeps 7 • Huge Projector • Designated Workspace
Lake

11. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (71 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥24,043
￥36,484 total
includes taxes & fees
Nov 1 - Nov 2
Kasa Lake Shore Chicago
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

12. 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.
The price is ￥17,066
￥46,853 total
includes taxes & fees
Oct 26 - Oct 27
Cozy, Comfortable and Convenient apartment. Close to everything!
A living room with a grey sofa, a white coffee table, and a grey rug.

13. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (25 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
The price is ￥16,782
￥36,885 total
includes taxes & fees
Oct 29 - Oct 30
Small hidden Gem. Location!
A modern bedroom with a bed, a sofa, and a hanging plant.

14. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (104 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 ￥9,955
￥22,034 total
includes taxes & fees
Nov 2 - Nov 3
Cozy studio in Andersonville Chicago
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

15. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
The price is ￥16,200
￥33,528 total
includes taxes & fees
Nov 2 - Nov 3
Chic Urban Retreat Near Wrigley Field w/Parking
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
The price is ￥11,125
￥62,483 total
includes taxes & fees
Oct 19 - Oct 20
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A rooftop terrace with a fire pit, seating area, and a city skyline view.

17. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is ￥17,208
￥37,414 total
includes taxes & fees
Nov 4 - Nov 5
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

18. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveler
The price is ￥11,502
￥12,725 total
includes taxes & fees
Oct 30 - Oct 31
2 Full Beds | Non-Smoking, Kitchen
A glass elevator with a city view.

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 ￥21,333
￥46,131 total
includes taxes & fees
Oct 27 - Oct 28
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"The hotel was great. The location, room, price, and the restaurant onsite. However there was a protest at 6am one of the days I stayed, right in front and under my room. It makes me not want to stay there again. It was brutal at 6am to hear screaming, chanting, and the bullhorn. It went on for over an hour and it was exhausting. The hotel needed to do something different."
Tenneal 2-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

Find out more about Far Southwest Side

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