Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Southwest Side

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (956)
"Great location and cleanliness of rooms. Staff was extremely helpful "
$160 nightly
The price is $188
Nov 10 - Nov 11
Total with taxes and fees
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (560)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
$192 nightly
The price is $225
Nov 3 - Nov 4
Total with taxes and fees
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very Good, (383)
"Great stay!"
$110 nightly
The price is $129
Nov 2 - Nov 3
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (239)
"Great stay. "
$135 nightly
The price is $159
Nov 2 - Nov 3
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (687)
"great room, clean good space and close to places "
$135 nightly
The price is $159
Oct 29 - Oct 30
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (363)
"nice area, shops nearby"
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
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
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
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 "
$135 nightly
The price is $159
Nov 9 - Nov 10
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
$257 nightly
The price is $302
Oct 19 - Oct 20
Total with taxes and fees
Kasa River North Chicago
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
$125 nightly
The price is $138
Oct 16 - Oct 17
Total with taxes and fees
Wrigleyville Suites
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
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!"
$118 nightly
The price is $139
Nov 9 - Nov 10
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (90)
"Super nice hotel and staff "
$200 nightly
The price is $229
Oct 29 - Oct 30
Total with taxes and fees
The Gem Museum Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
$289 nightly
The price is $340
Oct 16 - Oct 17
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (63)
"Good "
$94 nightly
The price is $106
Oct 20 - Oct 21
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
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. "
$135 nightly
The price is $159
Nov 2 - Nov 3
Total with taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments
Property amenity
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
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
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
9.2 out of 10, Wonderful, (27)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
$168 nightly
The price is $186
Nov 3 - Nov 4
Total with taxes and fees
Clean & Equipped 1BR Apt
2 bedrooms, iron/ironing board, travel crib, WiFi
Charming 2BR in Vibrant Lakeview
Charming 2BR in Vibrant Lakeview
9.4 out of 10, Exceptional, (20)
"This place was great! Loved my stay!"
$193 nightly
The price is $213
Oct 20 - Oct 21
Total with taxes and fees
Charming 2BR in Vibrant Lakeview
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University
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. "
$159 nightly
The price is $177
Oct 20 - Oct 21
Total with taxes and fees
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 Southwest Side Hotel Reviews

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"We did the corner suite and it was amazing waking up with the sunrise over the lake. "
Kole 1-night trip
Posted 11 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

Find out more about Southwest Side

Everything you need to know about 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 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 Southwest Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 $106 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 Southwest Side rentals

At Expedia, we put the best 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 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 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 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.

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