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4 Night Luxury vacations in South Side

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

Best Western Grant Park Hotel

Downtown Chicago

￥257,992

per person

Sep 8 - Sep 12

found 7 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.2/10 Very Good! (2,758 reviews)

El hotel le hace falta pintura en los pasillos y renovación de sus mobiliarios, lozas y baños. El piso del baño y bañera ya curtidos por el tiempo de uso. Por el lado del inhodoro tenía un hueco en el piso. El mueble del baño desgastado por el tiempo. Toallas deterioradas por el uso y el tiempo. Falta de seguridad frente al hotel. Mucho ruido en los pasillos.

Reviewed on Jul 30, 2026

Chinatown Hotel Chicago

Chinatown

￥276,656

per person

Oct 1 - Oct 5

found 6 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

5.6/10 (1,002 reviews)

It's cheap, but the hallways stink. But the rooms don't.

Reviewed on Jul 30, 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! (2,750 reviews)

"El hotel le hace falta pintura en los pasillos y renovación de sus mobiliarios, lozas y baños. El piso del baño y bañera ya curtidos por el tiempo de uso. Por el lado del inhodoro tenía un hueco en el piso. El mueble del baño desgastado por el tiempo. Toallas deterioradas por el uso y el tiempo. ..."

Reviewed on Jul 30, 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 pillowtop beds, designer toiletries, and more. The 2 bars, 24-hour ...

See all 454 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.