Southwest Side Vacation Rentals

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Our top choices for Southwest Side vacation rentals

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is CA $118
CA $389 total
includes taxes & fees
May 25 - May 26
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is CA $98
CA $362 total
includes taxes & fees
May 12 - May 13
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is CA $100
CA $321 total
includes taxes & fees
May 18 - May 19
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,159 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is CA $208
CA $284 total
includes taxes & fees
May 25 - May 26
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (752 reviews)
"Great location"
United States
Alex
The price is CA $242
CA $364 total
includes taxes & fees
May 12 - May 13
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (474 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is CA $304
CA $390 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (118 reviews)
"Perfect place to stay!"
United States
Anton
The price is CA $182
CA $208 total
includes taxes & fees
May 20 - May 21
The Gem Museum Suites

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
9.8 out of 10, Exceptional, (26 reviews)
"I had a fun stay "
United States
Jusu K.
The price is CA $196
CA $274 total
includes taxes & fees
May 13 - May 14
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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
The price is CA $135
CA $159 total
includes taxes & fees
May 13 - May 14
Wrigleyville Suites

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
The price is CA $336
CA $732 total
includes taxes & fees
Jun 3 - Jun 4
Cabin 105 by 747 Lofts

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.8 out of 10, Good, (7 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is CA $131
CA $271 total
includes taxes & fees
May 26 - May 27
Uptown Studio Gem Sum

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.6 out of 10, Exceptional, (9 reviews)
"Great location and very clean! "
United States
Camellia R.
The price is CA $250
CA $496 total
includes taxes & fees
May 13 - May 14
Furnished 3BR Apt w/ Laundry

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.2 out of 10, Wonderful, (18 reviews)
"Really great location. Clark street is great but can be a little noisy at night. "
United States
Adam
The price is CA $172
CA $369 total
includes taxes & fees
May 12 - May 13
Stylish and Roomy 2BR in Chicago

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (72 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is CA $218
CA $500 total
includes taxes & fees
May 19 - May 20
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is CA $254
CA $499 total
includes taxes & fees
May 27 - May 28
Kasa River North Chicago

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.
The price is CA $197
CA $468 total
includes taxes & fees
May 20 - May 21
Cozy, Comfortable and Convenient apartment. Close to everything!

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, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is CA $213
CA $780 total
includes taxes & fees
May 13 - May 14
Modern West Loop Gem-City Views & Prime Location 6

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (24 reviews)
"The location was perfect! The house very spacious, with more than enough room for my boys!"
United States
Carmen
The price is CA $263
CA $608 total
includes taxes & fees
May 13 - May 14
Spacious 3br home near Chicago, fenced yard for pets

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 CA $159
CA $308 total
includes taxes & fees
May 13 - May 14
Chic Studio in the Heart of the Gold Coast

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (36 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
The price is CA $141
CA $303 total
includes taxes & fees
May 12 - May 13
Nice 1BR Spot, Unwind & Relax
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

Find out more about Southwest Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.