Southwest Side, IL
Travel Guide
Visit Southwest Side
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
$153 nightly
The price is $178 total per night from Oct 25 to Oct 26
$178 total
Oct 25 - Oct 26
Total with taxes and 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
$169 nightly
The price is $201 total per night from Oct 25 to Oct 26
$201 total
Oct 25 - Oct 26
Total with taxes and 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
$153 nightly
The price is $182 total per night from Oct 25 to Oct 26
$182 total
Oct 25 - Oct 26
Total with taxes and 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! (10,209 reviews)
"This hotel needs to be updated se"
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
$25
per adult
90% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
LEGOLAND® Discovery Center Chicago
$26
per adult
92% of travellers recommend
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- Visit Rush Street
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- Griffin Museum of Science
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- Marquette Park
- S.S. Peter and Paul Church
- Wrigley Field
- Navy Pier
- Millennium Park
- Chicago Riverwalk
- Michigan Avenue
- United Center
- Lake Michigan
- Grant Park
- Donald E. Stephens Convention Center
- University of Chicago
- Northwestern University
- Willis Tower
- Indiana Dunes National Park
- Loyola University Chicago
- Art Institute of Chicago
- Allstate Arena
- Chicago Theatre
- Merchandise Mart
- Oakbrook Center Mall
- Water Tower Place