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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

￥227,954

per person

May 1 - May 5

just found

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

￥852,736

per person

May 2 - May 6

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

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

Great location and friendly staff

Reviewed on Feb 23, 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 ...

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.

8.2/10 Very Good! (2,686 reviews)

Great location and friendly staff

Reviewed on Feb 23, 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 ...

9.2/10 Wonderful! (1,068 reviews)

Clean and courteous staff

Reviewed on Feb 16, 2026

See all 471 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.