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4 Night Luxury vacations in South Side

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

Chinatown Hotel Chicago

Chinatown

￥285,328

per person

Mar 28 - Apr 1

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

5.4/10 (1,001 reviews)

Great for roding the cta

Reviewed on Jan 13, 2026

Best Western Grant Park Hotel

Downtown Chicago

￥323,231

per person

Mar 7 - Mar 11

found 8 hours ago

Roundtrip flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (2,619 reviews)

The staff was phenomenal and so helpful and accommodating on the Chicago Marathon weekend. The rooms were clean and they were great about keeping our linens fresh. Perfect place to stay, would book again!

Reviewed on Jan 25, 2026

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Top Luxury South Side Hotels

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Choose luxury at The Wheeler Mansion, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The lounge bar, terrace, and garden are ...

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

14 min drive from University of Chicago

Spoil yourself with a luxury vacation in Chicago. Popular amenities include a restaurant and a 24-hour fitness center.

8/10 Very Good! (2,670 reviews)

The staff was phenomenal and so helpful and accommodating on the Chicago Marathon weekend. The rooms were clean and they were great about keeping our linens fresh. Perfect place to stay, would book again!

Reviewed on Jan 25, 2026

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Choose luxury at Hyatt Regency McCormick Place Chicago , where you can enjoy amenities like massage services, pillowtop beds, and more. The 2 bars, 24-hour fitness ...

9/10 Wonderful! (1,061 reviews)

The room and staff were great

Reviewed on Jan 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.