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Far Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Far Southwest Side vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,259 reviews)
"The room and building were beautiful and located in a great place."
United States
Ryan
The price is NT$4,882
NT$6,679 total
includes taxes & fees
Aug 30 - Aug 31
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (516 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is NT$7,601
NT$9,720 total
includes taxes & fees
Aug 31 - Sep 1
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (13 reviews)
"Great location and super clean!"
United States
Erica
The price is NT$7,717
NT$11,094 total
includes taxes & fees
Sep 2 - Sep 3
Kasa Lake Shore Chicago
Living area

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.6 out of 10, Excellent, (49 reviews)
"would not recommend"
United States
heidi
The price is NT$7,112
NT$8,348 total
includes taxes & fees
Sep 8 - Sep 9
Wrigleyville Suites
Studio | Exterior

5. River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
River West, Second Floor Chicago by 747 Lofts
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

6. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$7,542
NT$12,216 total
includes taxes & fees
Aug 18 - Aug 19
Historic Oak Park Home
Apartment, Private Bathroom | Lounge

7. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NT$7,169
NT$11,788 total
includes taxes & fees
Aug 23 - Aug 24
At Home in Oak Park
House (3 Bedrooms) | Interior

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is NT$7,805
NT$15,314 total
includes taxes & fees
Aug 20 - Aug 21
Classic Forest Park Foursquare < 1 Mi to Blue Line
Interior

9. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Loved the space and location "
United States
Caroline
River West, Third Floor Chicago by 747 Lofts
Studio | Living area

10. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
Chicago Second Floor Studio by 747 Lofts
Studio | Living area

11. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is NT$4,291
NT$6,081 total
includes taxes & fees
Aug 23 - Aug 24
Ground Floor Studios in Chicago by 747 Lofts
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great place to stay , bar in hotel was very badly under staffed for everything going on in town that weekend. Would def stay here again!!"
Brian 1-night trip
Posted 1 hour ago
Hilton Chicago

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