South Side Adventure Vacations 2026

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Top Adventure vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.

Marriott Marquis Chicago

Near South Side

￥348,360

per person

Nov 9 - Nov 13

found 14 hours ago

Roundtrip flight included

Osaka (KIX) to Chicago (ORD)

9.2/10 Wonderful! (1,026 reviews)

Stayed for a Bears game and was super close to walk to the stadium. Great rooms and the team actually stayed as well

Reviewed on Sep 24, 2026

The Wheeler Mansion

Near South Side

￥499,870

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.6/10 Exceptional! (8 reviews)

Awesome stay. Close to Soldiers Field.

Reviewed on Sep 3, 2026

Hyatt Regency McCormick Place Chicago

Near South Side

￥447,148

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,359 reviews)

Convenient location with direct access to the convention center.

Reviewed on Sep 24, 2026

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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

￥325,111

per person

Nov 27 - Dec 1

found 16 hours ago

Roundtrip flight included

Osaka (KIX) to Chicago (ORD)

8.2/10 Very Good! (2,753 reviews)

Great hotel with a nice location! Love it!

Reviewed on Sep 24, 2026

The Wheeler Mansion

Near South Side

￥499,870

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.6/10 Exceptional! (8 reviews)

Awesome stay. Close to Soldiers Field.

Reviewed on Sep 3, 2026

Hyatt Regency McCormick Place Chicago

Near South Side

￥447,148

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,359 reviews)

Convenient location with direct access to the convention center.

Reviewed on Sep 24, 2026

Don't see what you're looking for?

See all available trips from Osaka to South Side

View all trips

Top Adventure South Side Hotels

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...

9.2/10 Wonderful! (1,450 reviews)

"Convenient location with direct access to the convention center."

Reviewed on Sep 24, 2026

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

14 min drive from University of Chicago

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 ...

8.2/10 Very Good! (2,733 reviews)

"Great hotel with a nice location! Love it!"

Reviewed on Sep 24, 2026

Jaslin Hotel

261 West Cermak Rd Chicago IL

11 min drive from University of Chicago

Stay at this 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 rooms in ...

See all 491 properties in South Side

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.