Far Southwest Side Vacation Packages
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Top Far Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,843, price is now CA $1,417 per person
CA $1,417
per person
Dec 25 - Dec 28
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Had a good stay. Will come again
Reviewed on Nov 2, 2026
Where to stay in Far Southwest Side
Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
Beverly
The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Childrens Museum of Oak Lawn and Martin Luther King Drive are a few top places to visit.
Far Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Dec 2 to Dec 3
CA $173
CA $206 total
Dec 2 - Dec 3
includes taxes & fees
8/10 Very good! (2,639 reviews)
"My room phone did not work and think it would be great to see a vending machine with needed items like Coke and snacks. Also think the staff could be dressed in a great uniform to represent the history of hotel in a modern way. I would be glad to have a call from hotel to discuss conversation or ..."
Reviewed on Nov 2, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
includes taxes & fees
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 Far Southwest Side attractions
What to do in Far Southwest Side
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
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- Chicago Theatre
- Willis Tower
- Lincoln Park Zoo
- Griffin Museum of Science and Industry
- Buckingham Fountain
- Grant Park
- The Loop Vacations
- Visit Cook County
- 875 North Michigan Avenue
- Chicago Riverwalk
- Visit Chicago
- Phoenix Vacations
- United Center
- Centennial Beach
- Ernest Hemingway Museum and House
- Marina City
- Golf Vacations
- Visit Downtown Chicago
- Frank Lloyd Wright Historic District
- Art Institute of Chicago
- Navy Pier
- Montrose Beach
- Unity Temple
- Wrigley Field
- Visit The Loop
- International Museum of Surgical Science
- Downtown Chicago Vacations
- Water Tower Place
- Chicago Vacations
- Robie House
- Millennium Park
- Lakeview Vacations
- Ann and Robert H. Lurie Children's Hospital
- Garfield Park Conservatory
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
