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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

￥320,665

per person

Jun 15 - Jun 19

found 11 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (2,685 reviews)

Breakfast at the pastry shop next door was good

Reviewed on May 3, 2026

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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 ...

9.2/10 Wonderful! (1,004 reviews)

Good food options including breakfast buffet which was great. Clean and well maintained property. Staff were very professional. My friend forgot her eye glasses in the room before check out and realized after. The staff went up and found it for her. They had fallen between the bed and nightstand. ...

Reviewed on May 4, 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 ...

9.2/10 Wonderful! (1,070 reviews)

Really nice and super clean

Reviewed on May 6, 2026

See all 472 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.