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Far Southwest Side Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Far Southwest Side holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,384 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,124
HK$1,319 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

2. 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, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is HK$636
HK$1,867 total
includes taxes & fees
28 Oct - 29 Oct
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Dining

3. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.2 out of 10, Wonderful, (22 reviews)
"Great little place not far from downtown. Clean apartment and a comfortable bed. Daughter slept on the couch and said it wasn't too bad. Everything worked as expected with no issues. Can hear people walking up the steps from time to time but overall pretty quiet. Took some time to find a parking spot but not the host's fault. Overall a great experience and would stay again."
United States
Garrett C.
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

4. 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 HK$720
HK$1,822 total
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

5. 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 HK$848
HK$2,327 total
includes taxes & fees
26 Oct - 27 Oct
Cozy, Comfortable and Convenient apartment. Close to everything!
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

6. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is HK$1,169
HK$2,396 total
includes taxes & fees
8 Nov - 9 Nov
2BR Apt with 2 Baths & Laundry
Lake

7. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
The price is HK$1,405
HK$2,063 total
includes taxes & fees
10 Nov - 11 Nov
Kasa Lake Shore Chicago
A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

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, (23 reviews)
The price is HK$934
HK$2,179 total
includes taxes & fees
26 Oct - 27 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A living room with a grey sofa, a white coffee table, and a grey rug.

9. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (26 reviews)
The price is HK$763
HK$1,748 total
includes taxes & fees
1 Nov - 2 Nov
Small hidden Gem. Location!
A modern living room with a blue sofa, a patterned rug, and a television.

10. 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)
The price is HK$487
HK$1,611 total
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
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, (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 HK$805
HK$1,656 total
includes taxes & fees
3 Nov - 4 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
Private kitchen

12. 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 traveller
The price is HK$2,354
HK$5,423 total
includes taxes & fees
5 Nov - 6 Nov
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A wooden deck with a railing, a staircase, and a window with a wreath.

13. 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.
The price is HK$1,123
HK$1,636 total
includes taxes & fees
22 Oct - 23 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A rooftop terrace with a brick wall, large windows, and a metal railing.

14. 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.
The price is HK$499
HK$2,028 total
includes taxes & fees
22 Oct - 23 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

15. 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, (30 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is HK$565
HK$2,107 total
includes taxes & fees
25 Oct - 26 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

16. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
South Loop
8.4 out of 10, Very good, (14 reviews)
The price is HK$1,217
HK$3,479 total
includes taxes & fees
26 Oct - 27 Oct
Smart Simple and Spacious 4BR Apt
A modern living room with teal sofas, a coffee table, and a TV.

17. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is HK$1,020
HK$1,259 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
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)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is HK$651
HK$905 total
includes taxes & fees
31 Oct - 1 Nov
Beautiful Rustic Cabin for Two!
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

19. 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.
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

20. 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.
The price is HK$649
HK$2,567 total
includes taxes & fees
22 Oct - 23 Oct
2BR Fitness Pad • Private Gym • Sleeps 7
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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