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, (1,144 reviews)
"Thank you for the stay"
United States
Marco
$177 nightly
The price is $208
May 25 - May 26
Total with taxes and fees
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (471 reviews)
"Very clean and nice place"
United States
Hector
$273 nightly
The price is $320
May 27 - May 28
Total with taxes and fees
Level Chicago – Old Town

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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.
$264 nightly
The price is $299
May 4 - May 5
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
$327 nightly
The price is $384
May 10 - May 11
Total with taxes and fees
Kasa River North Chicago

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$271 nightly
The price is $308
May 19 - May 20
Total with taxes and fees
West Loop Living – Bright 1BR

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, (5 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.
$536 nightly
The price is $615
May 26 - May 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
$743 nightly
The price is $847
May 13 - May 14
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
$229 nightly
The price is $258
May 3 - May 4
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
$305 nightly
The price is $360
May 7 - May 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR

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
$196 nightly
The price is $221
May 10 - May 11
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$276 nightly
The price is $316
May 9 - May 10
Total with taxes and fees
The Oak Park Loft

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$410 nightly
The price is $506
May 20 - May 21
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Everything went well"
United States
Ryan W.
$299 nightly
The price is $353
May 7 - May 8
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View

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
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
$179 nightly
The price is $201
May 3 - May 4
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Downtown Chicago Stay with Free In & Out Parking 2

Downtown Chicago Stay with Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location and the in/out parking was very convenient. The apartment was clean and had plenty of room. The Host was very attentive to our needs. "
United States
Patty H.
$591 nightly
The price is $677
May 3 - May 4
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 2

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
$268 nightly
The price is $307
May 4 - May 5
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (36 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
$289 nightly
The price is $339
May 12 - May 13
Total with taxes and fees
Wrigleyville Suites

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (35 reviews)
"Only needed some serving and cooking spoons, spatulas, etc., but as I was in a cooking class and not doing much cooking in the apartment it wasn't an issue. Lovely little spot, convenient, very comfortable and the host was available for any questions all hours of the day. Great stay. "
United States
Jan
$189 nightly
The price is $211
May 4 - May 5
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
$231 nightly
The price is $260
May 11 - May 12
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown

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, (68 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
$288 nightly
The price is $355
May 10 - May 11
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southwest Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Far Southwest Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Far Southwest Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $208 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Far Southwest Side rentals

At Expedia, we put the best Far Southwest Side vacation 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 vacation.

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.