Southwest Side
Travel Guide
Visit Southwest Side
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
The price is CA $202 per night from Oct 25 to Oct 26
CA $202
CA $251 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $241 per night from Sep 27 to Sep 28
CA $241
CA $287 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $228 per night from Oct 25 to Oct 26
CA $228
CA $271 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very good! (10,207 reviews)
"Good location, clean room. Property is worn out and dated."
Reviewed on Sep 24, 2026
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.
Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE Chicago IL
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (925 reviews)
"Super accommodation. Big. Roomy. Clean. Close to restaurants n shops. Despite communication being mostly via text.. the managers were VERY responsive. I would return in a jiffy to stay here.. Thank you. Thank you"
Reviewed on Sep 24, 2026
Kasa Lake Shore Chicago
446 East Ontario Street Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk are ...
8.4/10 Very good! (39 reviews)
"Great location and room"
Reviewed on Sep 24, 2026
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.
Stay near popular Southwest Side attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
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