Title: 5 Stars Hotels in South Side, Chicago from CA $326 - Find Cheap South Side Hotels With 5 Stars | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Richard Remington

# 5 Stars Hotels in South Side, Chicago from CA $326

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## Check availability on South Side 5 Star Hotels

Tonight

[Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-03&endDate=2026-01-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## 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](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Sophy Hyde Park

1411 East 53rd Street Chicago IL

CA $246

CA $326 total

Jan 18 - Jan 19

includes taxes & fees

9.4/10 Exceptional! (1,004 reviews)

[](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information)

Still don't see what you're looking for?

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[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&regionId=553248635074842823&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&regionId=553248635074842823&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&regionId=553248635074842823&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&regionId=553248635074842823&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&regionId=553248635074842823&star=50&star=50&amenities=WATER_PARK)

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](https://www.expedia.ca/Hotel-Search?startDate=2026-01-17&endDate=2026-01-18&adults=2&regionId=553248635074842823)

![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=900&h=514&p=1&q=high)

## Top South Side Hotel Reviews

## Find out more about South Side

Luxury is the name of the game at the best 5 Stars hotels in South Side. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top South Side 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars South Side hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels South Side without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in South Side.

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