Search Apartments in Southwest Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Apartments in Southwest Side and around

Our top choices for Southwest Side apartments

Twice as Nice: Chic 2BR Stay with Style & Space

9.0 out of 10, Wonderful, (2)
"Had a very nice time in Chicago!"
Twice as Nice: Chic 2BR Stay with Style & Space

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The One: A 1BR Stay That Feels Like Home

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is €211
includes taxes & fees
1 Sept - 2 Sept
Stylish 1BR in West Loop

South Loop | Rooftop With In & Out Parking

9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
South Loop | Rooftop With In & Out Parking

Your Chicago get Away

10.0 out of 10, Exceptional, (2)
"Clean, fun space and responsive host! Loved the views from our room!"
Your Chicago get Away

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

River North | Rooftop With In & Out Parking | 5

10.0 out of 10, Exceptional, (1)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
River North | Rooftop With In & Out Parking | 5

West Loop Living – Bright 1BR

The price is €233
includes taxes & fees
10 Sept - 11 Sept
West Loop Living – Bright 1BR

1BR Modern Luxe Apt with In-Unit Laundry

The price is €226
includes taxes & fees
10 Sept - 11 Sept
1BR Modern Luxe Apt with In-Unit Laundry

River North | Rooftop With In & Out Parking | 3

The price is €414
includes taxes & fees
14 Sept - 15 Sept
River North | Rooftop With In & Out Parking | 3

Historic Oak Park Home

2.0 star property
10.0 out of 10, Exceptional, (4)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
The price is €262
includes taxes & fees
21 Sept - 22 Sept
Historic Oak Park Home

3BR Luxury Modern Apartment

2.0 star property
9.2 out of 10, Wonderful, (13)
"Our family of 5 really enjoyed our stay! The apartment was awesome with a great view of downtown Chicago, and the location was safe and close to the city."
The price is €784
includes taxes & fees
10 Sept - 11 Sept
3BR Luxury Modern Apartment

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is €314
includes taxes & fees
9 Sept - 10 Sept
2-bedroom apartment just 2 minutes drive to Wrigley Field

The Oak Park Loft

2.0 star property
10.0 out of 10, Exceptional, (5)
"This apartment was is so cute! Hosts were awesome."
The Oak Park Loft

At Home in Oak Park

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is €329
includes taxes & fees
29 Sept - 30 Sept
At Home in Oak Park

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

2.0 star property
9.6 out of 10, Exceptional, (4)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
The price is €170
includes taxes & fees
2 Sept - 3 Sept
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Vintage Arcade Apt with Parking

2.0 star property
6.8 out of 10, (3)
"Very clean and private"
The price is €168
includes taxes & fees
22 Sept - 23 Sept
Vintage Arcade Apt with Parking

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

10.0 out of 10, Exceptional, (6)
"Very nice apartment close to downtown!"
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Mins to DT & Frank Lloyd Wright

2.0 star property
Mins to DT & Frank Lloyd Wright
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
Accommodation
Apartments
Lowest Price
Highest Price