South Side Beach Vacations 2026

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Top Beach vacation packages in South Side

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

Hyatt Regency McCormick Place Chicago

Near South Side

￥290,716

per person

Nov 9 - Nov 13

found 8 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,440 reviews)

Lit

Reviewed on Sep 30, 2026

Marriott Marquis Chicago

Near South Side

￥357,451

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Osaka (KIX) to Chicago (ORD)

9.2/10 Wonderful! (1,000 reviews)

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See all available trips from Tokyo to South Side

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4 Night Beach vacations in South Side

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

Chinatown Hotel Chicago

Chinatown

￥219,034

per person

Nov 9 - Nov 13

found 5 hours ago

Roundtrip non-stop flight included

Osaka (KIX) to Chicago (ORD)

5.6/10 (1,005 reviews)

Hyatt Regency McCormick Place Chicago

Near South Side

￥290,716

per person

Nov 9 - Nov 13

found 8 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,440 reviews)

Lit

Reviewed on Sep 30, 2026

Best Western Grant Park Hotel

Downtown Chicago

￥239,382

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Osaka (KIX) to Chicago (ORD)

8.2/10 Very Good! (2,747 reviews)

The picture on the website didn’t look like The room I stay in.

Reviewed on Sep 30, 2026

Don't see what you're looking for?

See all available trips from Osaka to South Side

View all trips

Top Beach South Side Hotels

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Stroll along the shore in Chicago, as you'll be near the beach with a holiday at this luxury, boutique hotel. Amenities at The Wheeler Mansion include a ...

9.6/10 Exceptional! (8 reviews)

"Awesome stay. Close to Soldiers Field."

Reviewed on Sep 3, 2026

Marriott Marquis Chicago

2121 South Prairie Avenue Chicago IL

11 min drive from University of Chicago

Enjoy your stay at this hotel and enjoy the sunsets on the beach in Chicago, as you'll be close to the beach. Amenities at Marriott Marquis Chicago include 9 ...

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! (1,473 reviews)

"Lit"

Reviewed on Sep 30, 2026

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.