Best Apartments in Southwest Side for Your Vacation from ￥22,944

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Our top choices for Southwest Side apartments

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

Brighton Park

Damary T.

￥44,192 total

includes taxes & fees

Aug 25 - Aug 26

A living room with a grey sofa, two chairs, a coffee table, and a small side table.

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

Brighton Park

Rachel

￥44,508 total

includes taxes & fees

Aug 25 - Aug 26

3. Spacious Apt | 4 Queen Beds | Free Parking

Brighton Park

￥56,094 total

includes taxes & fees

Aug 25 - Aug 26

A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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

Berwyn

Cynthia M.

￥28,967 total

includes taxes & fees

Aug 23 - Aug 24

A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

5. 3BR | Complete & Well-Located Apt in Hyde Park

Hyde Park

Nicolle C.

￥38,060 total

includes taxes & fees

Aug 24 - Aug 25

A modern kitchen with a large island, coffee maker, and a view of the city.

6. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

Lower West Side

Db D.

￥58,937 total

includes taxes & fees

Sep 8 - Sep 9

A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

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

Berwyn

Harquesha S.

￥28,387 total

includes taxes & fees

Aug 24 - Aug 25

A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

8. Smart Simple and Spacious 4BR Apt

Near South Side

James B.

￥65,671 total

includes taxes & fees

Aug 31 - Sep 1

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Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Prime location on the Mile. All Staff were top notch!"

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 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

Southwest Side Apartments information

Number of reviews	255
Accommodation	646 Apartments
Lowest Price	￥22,944
Highest Price	￥88,273

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Side apartments

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

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

3. Spacious Apt | 4 Queen Beds | Free Parking

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

5. 3BR | Complete & Well-Located Apt in Hyde Park

6. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

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

8. Smart Simple and Spacious 4BR Apt

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

10. Stylish 2BR Near Hyde Park, UChicago & Lake

11. 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

12. Flexhome East Village • Modern 2BR • Quiet Street

13. Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

14. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

15. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

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

17. Cozy studio in Andersonville Chicago

18. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

19. Stylish friendly 3BR Suite near McCormick

20. LIVN Millennium Park Downtown Chicago 1 BR

Find vacation rentals that suit your style

Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

Hotel Riu Plaza Chicago

The Chicago Hotel Collection - Magnificent Mile

Congress Plaza Hotel

Hyatt Regency Chicago

The Allegro Royal Sonesta Hotel Chicago Loop

L7 Chicago by LOTTE

Crowne Plaza Chicago West Loop by IHG

Find out more about Southwest Side

Southwest Side Apartments information

Explore a world of travel with Expedia

Apartments in Southwest Side for Rent

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Side apartments

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

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

3. Spacious Apt | 4 Queen Beds | Free Parking

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

5. 3BR | Complete & Well-Located Apt in Hyde Park

6. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

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

8. Smart Simple and Spacious 4BR Apt

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

10. Stylish 2BR Near Hyde Park, UChicago & Lake

11. 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

12. Flexhome East Village • Modern 2BR • Quiet Street

13. Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

14. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

15. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

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

17. Cozy studio in Andersonville Chicago

18. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

19. Stylish friendly 3BR Suite near McCormick

20. LIVN Millennium Park Downtown Chicago 1 BR

Find vacation rentals that suit your style

Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

Find out more about Southwest Side

Southwest Side Apartments information

Explore a world of travel with Expedia