Southwest Side
Travel Guide
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Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $147 per night from Sep 8 to Sep 9
CA $147
CA $175 total
Sep 8 - Sep 9
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is CA $193 per night from Aug 30 to Aug 31
CA $193
CA $230 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
The price is CA $218 per night from Sep 10 to Sep 11
CA $218
CA $303 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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.
Casa Midway Chicago - Spacious 1BR - Golf, City & Airport Access
Chicago IL
Stay at this apartment in Chicago. Enjoy a garden, laundry facilities, and air conditioning. Popular attractions Rate Field and SeatGeek Stadium are located ...
10/10 Exceptional! (2 reviews)
"We really enjoyed our stay! If ever in Chicago again, I’ll definitely stay here! Parking was a little tricky but otherwise, just the right amount of updates while maintaining the classic style of the space."
Reviewed on Jun 21, 2026
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 ...
9.2/10 Wonderful! (1,247 reviews)
"It was such a great room and early check-in was super convenient."
Reviewed on Aug 9, 2026
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! (845 reviews)
"No good value for money , the apartment standards did not match the cost . The property does not also advise that you have to pay a fee (deposit) at check in . I doubt if I would stay there again"
Reviewed on Aug 10, 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
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
LEGOLAND® Discovery Center Chicago
CA $41
per adult
92% of travellers recommend
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