South Side Beach Vacations 2026

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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

￥284,559

per person

Nov 2 - Nov 6

found 8 hours ago

Roundtrip flight included

Kobe (UKB) to Chicago (ORD)

8.2/10 Very Good! (2,779 reviews)

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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 ...

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! (1,360 reviews)

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Reviewed on Sep 1, 2026

See all 468 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.