South Side Beach Vacations 2026

Plan, book, travel with confidence
Better together
Save up to ￥109,000 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 Beach vacation packages in South Side

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

Marriott Marquis Chicago

Near South Side

￥313,270

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,006 reviews)

Clean and found the location convenient. Price seemed very high.

Reviewed on Aug 16, 2026

Don't see what you're looking for?

See all available trips from Tokyo to South Side

View all trips

3 Night Beach vacations in South Side

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

Marriott Marquis Chicago

Near South Side

￥313,270

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,006 reviews)

Clean and found the location convenient. Price seemed very high.

Reviewed on Aug 16, 2026

Don't see what you're looking for?

See all available trips from Tokyo to South Side

View all trips

4 Night Beach vacations in South Side

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

Best Western Grant Park Hotel

Downtown Chicago

￥291,065

per person

Nov 3 - Nov 6

found 16 hours ago

Roundtrip flight included

Osaka (KIX) to Chicago (ORD)

8.2/10 Very Good! (2,754 reviews)

Marriott Marquis Chicago

Near South Side

￥402,340

per person

Oct 7 - Oct 11

found 23 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,006 reviews)

Clean and found the location convenient. Price seemed very high.

Reviewed on Aug 16, 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 ...

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 ...

9.2/10 Wonderful! (1,006 reviews)

"Clean and found the location convenient. Price seemed very high."

Reviewed on Aug 16, 2026

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 ...

See all 461 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.