South Side Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Adventure vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago
Near South Side
Price was ￥372,396, price is now ￥348,278 per person
￥348,278
per person
Jan 2 - Jan 8
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,012 reviews)
Huge convention center associated hotel. Very nice clean and modern rooms. Lakeside views from the convention are amazing (watch it at Sunrise). Only con is that it's kind of isolated dining wise and from more hip or active parts of the city. taxis/rideshares making a killing over here.
Reviewed on Oct 22, 2025
4 Night Adventure vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel
Downtown Chicago
Price was ￥189,335, price is now ￥186,638 per person
￥186,638
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,628 reviews)
For the price NO. The best option if it is available is to stay somewhere near the end of one of the L-trains with a day pass and make your way in and around town.
Everyone I ask sad the noise from the mechanical things on the roof (9th) floor rooms was horrible. On my floor the road noise and the L-train was almost load. Sub $250 it’s OK, anything higher it’s a VERY maybe stay for me.
Dinning options around the area a very good.
Reviewed on Oct 14, 2025
Top Adventure South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,024 reviews)
Will be back!
Reviewed on Oct 24, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,637 reviews)
It was good
Reviewed on Oct 19, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,167 reviews)
Room was clean and staff were friendly with check-in and giving me extra pillows. The bed was comfortable. The hotel ia in the heart of chinatown with great restaurants, pretty conveniently walkable to McCormick center. Overall very happy with my stay here.
Reviewed on Oct 24, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
