Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Southwest Side vacation rentals

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (426 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,075 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is NT$3,444
NT$4,965 total
includes taxes & fees
Feb 23 - Feb 24
Sentral Michigan Avenue
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

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
The price is NT$3,997
NT$8,063 total
includes taxes & fees
Feb 15 - Feb 16
The Oak Park Loft
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is NT$4,330
NT$8,445 total
includes taxes & fees
Mar 1 - Mar 2
Historic Oak Park Home
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is NT$3,731
NT$4,380 total
includes taxes & fees
Feb 15 - Feb 16
Wrigleyville Suites
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is NT$2,142
NT$10,634 total
includes taxes & fees
Feb 15 - Feb 16
Chicago Third Floor Studio by 747 Lofts
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (104 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is NT$5,710
NT$6,537 total
includes taxes & fees
Feb 15 - Feb 16
The Gem Museum Suites
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
Harvey
4.2 out of 10, (71 reviews)
"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"
United States
Destin
The price is NT$2,657
NT$3,002 total
includes taxes & fees
Feb 16 - Feb 17
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (694 reviews)
"Big, luxury, easy parking "
United States
Chanel
Kasa Magnificent Mile Chicago
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is NT$3,769
NT$7,802 total
includes taxes & fees
Feb 15 - Feb 16
At Home in Oak Park
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is NT$2,513
NT$6,364 total
includes taxes & fees
Feb 15 - Feb 16
Historic Oak Park Residence
Interior

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, (17 reviews)
"Loved the space and location "
United States
Caroline
River West, Third Floor Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (21 reviews)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
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 Southwest Side Hotel Reviews

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"It was a nice time. Ill be bringing my dog next time"
Shayna 2-night trip
Posted 3 hours ago
Aloft Chicago Mag Mile

Find out more about Southwest Side

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