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Far Southwest Side Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (1,354 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
The price is HK$1,438
HK$1,688 total
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (55 reviews)
"Location is perfect"
United States
Mary
The price is HK$1,405
HK$2,137 total
includes taxes & fees
5 Nov - 6 Nov
Kasa Lake Shore Chicago
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

3. 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 HK$1,122
HK$2,311 total
includes taxes & fees
2 Nov - 3 Nov
2BR Apt with 2 Baths & Laundry
Terrace/patio

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,504
HK$2,593 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

5. 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.
The price is HK$1,161
HK$2,407 total
includes taxes & fees
15 Oct - 16 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

6. 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.
The price is HK$796
HK$1,628 total
includes taxes & fees
26 Oct - 27 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (535 reviews)
"Location and facility was very nice"
United States
Brian
The price is HK$1,781
HK$2,284 total
includes taxes & fees
2 Nov - 3 Nov
Level Chicago – Old Town
Private kitchen

8. 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.
The price is HK$628
HK$1,743 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A bedroom with a bed, bedside lamp, wall-mounted mirror, and a rug.

9. 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
The price is HK$832
HK$1,896 total
includes taxes & fees
2 Nov - 3 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
Private kitchen

10. 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$5,354 total
includes taxes & fees
2 Nov - 3 Nov
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

11. 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.
The price is HK$531
HK$1,408 total
includes taxes & fees
19 Oct - 20 Oct
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A living room with a grey sofa, a white coffee table, and a grey rug.

12. 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 HK$847
HK$1,830 total
includes taxes & fees
2 Nov - 3 Nov
Small hidden Gem. Location!
A rooftop terrace with a fire pit, seating area, and a city skyline view.

13. 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 HK$1,821
HK$3,077 total
includes taxes & fees
19 Oct - 20 Oct
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

14. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$854
HK$1,849 total
includes taxes & fees
28 Oct - 29 Oct
The Oak Park Loft
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

15. 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.
The price is HK$600
HK$1,549 total
includes taxes & fees
12 Oct - 13 Oct
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

16. 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.
The price is HK$539
HK$1,424 total
includes taxes & fees
14 Oct - 15 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

17. 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.
The price is HK$552
HK$2,385 total
includes taxes & fees
27 Oct - 28 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (101 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is HK$494
HK$1,094 total
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A modern living room with a blue sofa, a patterned rug, and a television.

19. 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.
The price is HK$549
HK$1,709 total
includes taxes & fees
13 Oct - 14 Oct
Great Area Logan Square Apt Games Pets - Sleeps 5
A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

20. 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
The price is HK$897
HK$1,547 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
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 Wade

The Wade

10/10 Excellent
"The room was clean, the staff was helpful, and the views were top tier!"
Latoya 2-night trip
Posted less than an hour ago
The Wade

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