Photo by by Midway Intl Airport

Search Apartments in Southwest Side

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

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

Brighton Park
9.2 out of 10, Wonderful, (7)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is €227
includes taxes & fees
8 Dec - 9 Dec
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

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

Brighton Park
8.6 out of 10, Excellent, (20)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

4BR Corporate Suite Central and Modern

2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is €1,183
includes taxes & fees
30 Nov - 1 Dec
4BR Corporate Suite Central and Modern

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is €156
includes taxes & fees
1 Dec - 2 Dec
Gold Coast Living: Modern Studio Unit

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is €141
includes taxes & fees
1 Dec - 2 Dec
West Loop Living – Bright 1BR

Sleek 1BR Apt w/ Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is €141
includes taxes & fees
2 Dec - 3 Dec
Sleek 1BR Apt w/ Laundry

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is €141
includes taxes & fees
3 Dec - 4 Dec
The One: A 1BR Stay That Feels Like Home

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
The price is €142
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is €141
includes taxes & fees
30 Nov - 1 Dec
Stylish 1BR in West Loop

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is €280
includes taxes & fees
7 Dec - 8 Dec
River North Rooftop With In and Out Parking 1

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is €141
includes taxes & fees
7 Dec - 8 Dec
1BR Modern Luxe Apt with In-Unit Laundry

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
South Loop Rooftop With In and Out Parking 3

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is €369
includes taxes & fees
1 Dec - 2 Dec
Your Chicago get Away

River North Private Deck With In and Out Parking

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is €635
includes taxes & fees
26 Dec - 27 Dec
River North Private Deck With In and Out Parking

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

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is €161
includes taxes & fees
30 Nov - 1 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Complete 1BR Home Sum

Downtown Chicago
The price is €141
includes taxes & fees
30 Nov - 1 Dec
Complete 1BR Home Sum

Relaxing Chicago Studio

Edgewater
9.8 out of 10, Exceptional, (36)
"Had a great stay. Great location. "
United States
Justin
The price is €137
includes taxes & fees
1 Dec - 2 Dec
Relaxing Chicago Studio

Cozy Clean Chicago Apartment Free Street Parking Near Downtown Washer & Dryer

West Ridge
10.0 out of 10, Exceptional, (4)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is €251
includes taxes & fees
1 Dec - 2 Dec
Cozy Clean Chicago Apartment Free Street Parking Near Downtown Washer & Dryer

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is €180
includes taxes & fees
2 Dec - 3 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Montrose Studio:Your Uptown Base

Uptown
9.8 out of 10, Exceptional, (7)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
The price is €138
includes taxes & fees
1 Dec - 2 Dec
Montrose Studio:Your Uptown Base
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

Southwest Side Apartments information

Number of reviews
128
Accommodation
702 Apartments
Lowest Price
€137
Highest Price
€1,183