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Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Southwest Side vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,188 reviews)
"Great location"
United States
JAVIER
$203 nightly
The price is $238
Jul 1 - Jul 2
Total with taxes and fees
Sentral Michigan Avenue
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, (492 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$274 nightly
The price is $322
Jun 29 - Jun 30
Total with taxes and fees
Level Chicago – Old Town
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (135 reviews)
"Perfect place to stay!"
United States
Anton
$152 nightly
The price is $174
Jun 17 - Jun 18
Total with taxes and fees
The Gem Museum Suites
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$275 nightly
The price is $314
Jun 30 - Jul 1
Total with taxes and fees
The Oak Park Loft
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (38 reviews)
"Amazing !!!!! Would stay again, clean, beautiful Spot, great area !"
United States
Luka
$264 nightly
The price is $310
Jul 7 - Jul 8
Total with taxes and fees
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
$270 nightly
The price is $317
Jun 17 - Jun 18
Total with taxes and fees
Chicago Third Floor Studio by 747 Lofts
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)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
$258 nightly
The price is $296
Jun 28 - Jun 29
Total with taxes and fees
Historic Oak Park Home
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)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
$353 nightly
The price is $404
Jun 22 - Jun 23
Total with taxes and fees
Historic Oak Park Residence
Studio | Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
$162 nightly
The price is $191
Jun 24 - Jun 25
Total with taxes and fees
Cabin 105 by 747 Lofts
Studio | Living area

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, (22 reviews)
"Great area and surprisingly nice room!"
United States
Michael
$143 nightly
The price is $168
Jun 15 - Jun 16
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
Studio | Living area

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (13 reviews)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
$242 nightly
The price is $284
Jun 21 - Jun 22
Total with taxes and fees
Chicago Second Floor Studio 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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"It's a very unique and different hotel, however, it's in a historic building, so you will learn to understand it's uniqueness."
Dorothy 2-night trip
Posted less than an hour ago
Congress Plaza Hotel

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 $105 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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