5 Star Hotels in South Side, Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on South Side 5 Star Hotels

Top South Side 5 Star Hotels

Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in South Side.
Sophy Hyde Park

Sophy Hyde Park

1411 East 53rd Street, Chicago, IL
The price is €231 per night from 2 Sept to 3 Sept
€231
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Still don't see what you're looking for?
See all properties in South Side.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan.

See all hotels in South Side

Top South Side Hotel Reviews