Far Southwest Side Vacation Rentals

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Our top choices for Far Southwest Side vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,094 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ¥17,097
¥24,646 total
includes taxes & fees
Mar 3 - Mar 4
Sentral Michigan Avenue

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ¥19,830
¥38,013 total
includes taxes & fees
Mar 18 - Mar 19
Sleek 1BR Apartment w/ In-unit Laundry

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is ¥17,618
¥36,168 total
includes taxes & fees
Mar 1 - Mar 2
West Loop Living – Bright 1BR

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ¥17,618
¥34,226 total
includes taxes & fees
Mar 1 - Mar 2
Chic Studio in the Heart of the Gold Coast

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ¥17,644
¥35,452 total
includes taxes & fees
Mar 8 - Mar 9
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ¥17,618
¥36,168 total
includes taxes & fees
Mar 1 - Mar 2
Modern Comfort: 1BR Unit w/ Laundry

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is ¥20,892
¥56,287 total
includes taxes & fees
Mar 1 - Mar 2
River North Rooftop With In and Out Parking 3

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (433 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
The price is ¥44,781
¥56,422 total
includes taxes & fees
Feb 28 - Mar 1
Level Chicago – Old Town

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥17,618
¥35,978 total
includes taxes & fees
Mar 2 - Mar 3
1BR Modern Luxe Apt with In-Unit Laundry

NEW Private West Loop 1br with Backyard near Green Line and CTA

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
9.6 out of 10, Exceptional, (4 reviews)
"Very cozy stay. Host was great with communication and the place has everything needed. Would definitely book here again!"
United States
Eric H.
The price is ¥6,011
¥32,463 total
includes taxes & fees
Mar 17 - Mar 18
NEW Private West Loop 1br with Backyard near Green Line and CTA

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (26 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ¥10,758
¥27,364 total
includes taxes & fees
Mar 1 - Mar 2
Nice 1BR Spot, Unwind & Relax

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
10.0 out of 10, Exceptional, (51 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
The price is ¥9,355
¥24,050 total
includes taxes & fees
Mar 2 - Mar 3
Relaxing Chicago Studio

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is ¥12,643
¥34,464 total
includes taxes & fees
Mar 2 - Mar 3
A quiet stay while you are away

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.8 out of 10, Excellent, (20 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
The price is ¥10,461
¥16,088 total
includes taxes & fees
Feb 28 - Mar 1
Beautiful Rustic Cabin for Two!

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥18,101
¥46,957 total
includes taxes & fees
Mar 1 - Mar 2
2-bedroom apartment just 2 minutes drive to Wrigley Field

Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
9.8 out of 10, Exceptional, (14 reviews)
"Clean and great location"
United States
Margo M.
The price is ¥10,774
¥27,404 total
includes taxes & fees
Mar 2 - Mar 3
Homey 1BR Space Apartment

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is ¥10,758
¥27,364 total
includes taxes & fees
Mar 1 - Mar 2
Charming Sunlit 1BR Apartment

Ideal 2BR Getaway Close to Attractions

Ideal 2BR Getaway Close to Attractions
Rogers Park
8.4 out of 10, Very Good, (7 reviews)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
United States
Ever
The price is ¥11,537
¥30,809 total
includes taxes & fees
Mar 1 - Mar 2
Ideal 2BR Getaway Close to Attractions

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Glad to have found this gem in Oak Park for a two-night stay with friends. Booking and checking in was easy and seamless. Free street parking was a huge bonus. The space was super cute and comfortable. We enjoyed walking around the neighborhood and getting into the city was super easy (we chose to use Lyft instead of the train, but there are train stations within walking distance. Would definitely book this property again the next time I come to Chicago."
United States
Emily B.
The price is ¥16,838
¥45,870 total
includes taxes & fees
Mar 1 - Mar 2
Cozy, Comfortable and Convenient apartment. Close to everything!

Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
9.4 out of 10, Exceptional, (9 reviews)
"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "
United States
Sharlene T.
The price is ¥11,693
¥30,798 total
includes taxes & fees
Mar 3 - Mar 4
Homey 2BR Apt 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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