Southwest Side Vacation Rentals from $145: Search Short-Term Rentals

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Our top choices for Southwest Side vacation rentals

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

Brighton Park

Rachel

$251 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Brighton Park

Yiu S.

$223 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Brighton Park

Damary T.

$249 nightly

Aug 24 - Aug 25

Total with taxes and fees

2 bedrooms, desk, iron/ironing board, WiFi

4. Spacious Apt | 4 Queen Beds | Free Parking

Brighton Park

$344 nightly

Aug 25 - Aug 26

Total with taxes and fees

5. Sentral Michigan Avenue

Downtown Chicago

Heather

$176 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Kasa Lake Shore Chicago

Downtown Chicago

Erica

$208 nightly

Sep 10 - Sep 11

Total with taxes and fees

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

Berwyn

Cynthia M.

$170 nightly

Aug 23 - Aug 24

Total with taxes and fees

Full-size fridge, microwave, oven, stovetop

8. Level Chicago – Old Town

Downtown Chicago

Martha

$293 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

10/10 Excellent

"Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"I have been reading reviews on various websites that sacred me immensely before checking in. All the reviews spoke negatively about the extra charges, so I reached out to the hotel and asked them twice about these charges and was assured both times that since I booked only a room, I will not be charged extra. Safe to say, people booking extra amenities need to share the blame when they are faced with these extra charges because the details are listed on the website. I was pleasantly surprised by the hotel which is conveniently located close to all the attractions. I was able to either walk or take a train ride from the closest subway station. Aside from a very overpowering smell that greets you when you walk in (to which your nose gets fatigued to in a minute or two) I found the room to be well decorated and comfortable."

Congress Plaza Hotel

10/10 Excellent

"This is our 2nd time staying here, our 1st was for a wedding held there last year. It was great & we stayed in a renovated room. Amazing & we will be back. Rooms were spacious, very clean, & amazing room. We decided to splurge & upgrade to a lakeside view. Check in was easy, great area, & love that they can hold baggage as well after you check out. Lastly great sleep! Bed was very comfy & pillows were amazing. Until next time"

The Wade

10/10 Excellent

"The lobby felt so classy and the whole hotel had this sort of dark ambiance with warm lighting which felt calm and inviting. To go along, the check in process was quick and to the point. When getting off the elevator of the floor where my room was at, the corridors were beautifully thought through and followed the brand of the hotel. Then, opening the door to my room for the night was a great feeling starting with the view of downtown Chicago which was incredible, especially at night. The room and bathroom were very clean, no complaints whatsoever. The wade also offered great amenities like the heated indoor pool which closed pretty late as well as the fitness center. The Ohio street beach was also an 4-5 minute or less walk away from the hotel, sadly it was raining the whole day but we still enjoyed the indoor pool after dinner. Overall me and my partner really enjoyed our short trip at the wade in downtown Chicago and we will definitely keep this hotel in mind when we go back to Chicago."

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"This is a beautiful hotel and wonderful staff. We loved the design and the decor. The coffee area was so well set up and very thoughtful with honey, almond milk, lemons for water and tea. Very clean and delicious. The gym was a bit small but had all of the equipment and weights needed. They had chilled eucalyptus face towels that I loved so much at the end of my workout. The location was great. We loved the Nederlander theater and seeing The Notebook! My husband and I had an amazing time. Chicago was great! This hotel will not disappoint."

L7 Chicago by LOTTE

10/10 Excellent

"L7 is centrally located and is the perfect hotel for exploring the city. Easy access to everything. Clean property and more boutique and small compared to the larger hotels, which I prefer. The staff was amazing. So very friendly - especially Alex at the front desk. It was so nice that he was the first person we met because he set the tone for a wonderful trip. He answered every question and was so pleasant and helpful. He truly took great care of us! I look forward to coming back!"

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 $145 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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Check prices for these dates

Our top choices for Southwest Side vacation rentals

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

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

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

4. Spacious Apt | 4 Queen Beds | Free Parking

5. Sentral Michigan Avenue

6. Kasa Lake Shore Chicago

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

8. Level Chicago – Old Town

9. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

10. Cozy studio in Andersonville Chicago

11. LIVN West Loop Chicago Classic Queen Studio

12. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

13. 3BR | Complete & Well-Located Apt in Hyde Park

14. LIVN Millennium Park Downtown Chicago 1 BR

15. Smart Simple and Spacious 4BR Apt

16. Chic Urban Retreat Near Wrigley Field w/Parking

17. Spacious 4BR Central Apartment w/ Skyline Views

18. Group-Friendly 4BR Hyde Park Retreat Near UChicago

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

20. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Find vacation rentals that suit your style

Top Southwest Side Hotel Reviews

Hotel Riu Plaza Chicago

Find out more about Southwest Side

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