Search Apartments in Southwest Side
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Southwest Side apartments
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
Yiu S.
The price is AED 386
AED 1,005 total
includes taxes & fees
13 Jul - 14 Jul
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | ArcadeBrighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
Jessica H.
The price is AED 349
AED 1,066 total
includes taxes & fees
30 Jun - 1 Jul
LIVN West Loop Chicago Queen Superior Studio
LIVN West Loop Chicago Queen Superior StudioDowntown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
Michelle R.
The price is AED 676
AED 911 total
includes taxes & fees
21 Jun - 22 Jun
River North Rooftop With In and Out Parking 5
River North Rooftop With In and Out Parking 5Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
Jacob
The price is AED 1,039
AED 2,101 total
includes taxes & fees
9 Jul - 10 Jul
Modern West Loop Gem-City Views & Prime Location 5
Modern West Loop Gem-City Views & Prime Location 5Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great stay."
Mollie A.
The price is AED 672
AED 2,217 total
includes taxes & fees
7 Jul - 8 Jul
River North Rooftop With In and Out Parking 3
River North Rooftop With In and Out Parking 3Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
Jennifer M.
The price is AED 973
AED 2,208 total
includes taxes & fees
1 Jul - 2 Jul
Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago Stay with Free In & Out Parking 5Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
Gina C.
The price is AED 867
AED 2,063 total
includes taxes & fees
7 Jul - 8 Jul
3BR Luxury Suite w/Gym and Balcony
3BR Luxury Suite w/Gym and BalconyDowntown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
Cassidy L.
The price is AED 1,363
AED 2,810 total
includes taxes & fees
1 Jul - 2 Jul
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Southwest Side Hotel Reviews
Hyatt Regency O'Hare Chicago
10/10 Excellent
