Southwest Side Vacation Rentals from $88: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Southwest Side vacation rentals

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

Brighton Park

Rachel

$263 nightly

Jun 15 - Jun 16

Total with taxes and fees

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

Brighton Park

Jessica H.

$285 nightly

Jun 30 - Jul 1

Total with taxes and fees

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

Brighton Park

Yiu S.

$239 nightly

Jun 15 - Jun 16

Total with taxes and fees

Sentral Michigan Avenue

Downtown Chicago

Karen

$203 nightly

Jul 1 - Jul 2

Total with taxes and fees

Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Downtown Chicago

Dulce

$208 nightly

Jun 15 - Jun 16

Total with taxes and fees

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Kimberly

$272 nightly

Jun 30 - Jul 1

Total with taxes and fees

Chic Suite/Mins to L Train /Laundry/Free Parking

Oak Park

Tamela S.

$206 nightly

Jun 9 - Jun 10

Total with taxes and fees

Iron/ironing board, travel crib, WiFi, bed sheets

Homey Hyde Park Studio Near UChicago

Hyde Park

Meg D.

$174 nightly

Jun 9 - Jun 10

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Southwest Side Hotel Reviews

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Staff is friendly and helpful. Rooms are sparking clean. Valet parking and complimentary breakfast are valuable amenities"

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"I thought the staff was excellent as they helped us with the baggage along with letting us check in a few hours early. They had another convention or something that was meeting in the lobby and everything went smoothly and uninterrupted.. make sure you get the breakfast too because it’s as good as it gets. I would recommend it again."

Eurostars Magnificent Mile

2/10 Terrible

"No amenities. Bathroom sink has a crack and hair in it. A/C unit makes a lot of noise all night long and abruptly turns on and off so it startles you out of sleep all night long. Located across from apartment bldg and even though I was on a high floor the people across the street in high rise apartment had a very loud balcony party until 2am so the Location is not good. Desk girl was rude. Not at all helpful when I asked her about dinner options close by. Basically said “you need to google that”. We were asking what is closest for walking as it was later after 8pm on a weeknight and places close early. Also concerned about safety of walking after dark vs getting uber. She offered no suggestions of any places. Acted like she didn’t want to be there. Another guest’s luggage had been in hold room while they were out and when they came to gather it (as we were checking in) the staff was frantic bc it was “lost”. It wasn’t found in the 15 minutes we were checking in. I wouldn’t trust this hotel. And I’ll never stay here again. First & Last for me."

Congress Plaza Hotel

6/10 Okay

"Location was good to train station and grand park but biggest issue we had is no water pressure and it was at best lukewarm. This makes me now want to always check first before booking anything how their water service is. It was terrible and when I checked previous reviews it was one of biggest complaints. For this reason alone we won’t me back since after checking out downtown and traveling on the L to games and different places from south side to north side Chicago, you want to be able to have a decent shower and unwind."

Freehand Chicago

6/10 Okay

"It was a really neat hotel. I liked the style. Wasn't sure why we had to make our own beds though. Also, the phone didn't work in the room, so I tried to call the front desk from my phone. They immediately put me on hold "for a minute", which turned into 5. I hung up to call back thinking they forgot about me, they did the same thing AGAIN. I thought, "Well third time's a charm, right?"-- wrong. Same thing! What if it had been an emergency(flooded room, or something-- not 911 eligible)? It's not like a short trip to the front desk to ask in person. The lady at the café was nice and the food was decent."

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 $88 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.

Southwest Side Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Southwest Side vacation rentals

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

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

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

Sentral Michigan Avenue

Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Chic Suite/Mins to L Train /Laundry/Free Parking

Homey Hyde Park Studio Near UChicago

West Loop Living – Bright 1BR

Cozy studio in Andersonville Chicago

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

River North Rooftop With In and Out Parking 5

Chicago-Themed 1BR in a Central Spot near Downtown

Vibrant 1BR Apartment

The Oak Park Loft

2 Full Beds | Non-Smoking, Kitchen

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Sunlit Studio with City Charm

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Find vacation rentals that suit your style

Top Southwest Side Hotel Reviews

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Find out more about Southwest Side

Explore a world of travel with Expedia

Expedia's Latest Trends

Go further with the Expedia app