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Far Southwest Side Holiday Rentals

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Holiday Rentals in Far Southwest Side

House with garage, outdoor dining and basement bar
7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (958)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is AU$289
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (563)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (384)
"Great stay!"
The price is AU$198
includes taxes & fees
5 Nov - 6 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (239)
"Great stay. "
The price is AU$244
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (689)
"Location was nice."
The price is AU$244
includes taxes & fees
29 Oct - 30 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (363)
"An excellent place to stay in Chicago downtown."
Kasa South Loop Chicago
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (210)
"Perfect location and area was wonderful."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
The price is AU$228
includes taxes & fees
16 Nov - 17 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Kasa River North Chicago
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
The price is AU$355
includes taxes & fees
18 Oct - 19 Oct
Wrigleyville Suites
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
The price is AU$213
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Stylish Apartment near Chicago Downtown
2.0 star property
The price is AU$521
includes taxes & fees
19 Oct - 20 Oct
Stylish Apartment near Chicago Downtown
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (63)
"Good "
The price is AU$147
includes taxes & fees
20 Oct - 21 Oct
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is AU$244
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Clean & Equipped 1BR Apt
9.2 out of 10, Wonderful, (28)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
The price is AU$289
includes taxes & fees
3 Nov - 4 Nov
Clean & Equipped 1BR Apt
Charming 2BR in Vibrant Lakeview
9.4 out of 10, Exceptional, (20)
"This place was great! Loved my stay!"
The price is AU$330
includes taxes & fees
20 Oct - 21 Oct
Charming 2BR in Vibrant Lakeview
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (7)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$277
includes taxes & fees
29 Oct - 30 Oct
Cozy Studio in Hyde Park-Walk to Lake & University
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

Find out more about Far Southwest Side

Everything you need to know about Far Southwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Far Southwest Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Far Southwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Far Southwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Far Southwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Far Southwest Side holiday rentals we have selected for you start as low as AU$147 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Far Southwest Side rentals

At Expedia, we put the best Far Southwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Far Southwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Far Southwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Far Southwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.