Luxury Hotels, South Side Chicago | Expedia

A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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Check availability on South Side Luxury Hotels

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Sep 29 - Sep 30

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Our top choices for South Side luxury hotels

A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.

A bar area with a marble countertop, multiple shelves of bottles, and a large TV screen. There are several bar stools and a round table with a vase of flowers.

A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.

An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.

1. Sophy Hyde Park

Hyde Park

Luxury meets cultural charm in Hyde Park Chicago, where plush bedding and upscale dining create an elegant retreat near lakefront parks.

P18,013

P22,981 total

includes taxes & fees

Oct 30 - Oct 31

A large, historic building with a central courtyard surrounded by trees.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

2. Hilton Chicago

Downtown Chicago

P10,367

P14,161 total

includes taxes & fees

Oct 30 - Oct 31

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

3. The Wade

Downtown Chicago

Luxurious lakeside retreat in downtown Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.

P9,319

P11,079 total

includes taxes & fees

Oct 25 - Oct 26

A modern building with the name 'SENIORAL' prominently displayed on the facade.

A modern kitchen with a built-in microwave, stove, and dishwasher, large windows with city views, and a dining area with a table and chairs.

A modern kitchen with a large island, bar stools, and a view of the city skyline.

A bar area with stools, a counter with bottles, and a wall with a leafy design.

4. Sentral Michigan Avenue

Downtown Chicago

P10,958

P14,699 total

includes taxes & fees

Oct 26 - Oct 27

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A grilled pineapple on top of a stack of meat, served on a pan.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

A conference room with a long table, chairs, and a projector screen.

5. Hyatt Centric The Loop Chicago

Downtown Chicago

P16,824

P21,567 total

includes taxes & fees

Oct 29 - Oct 30

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

6. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

P17,012

P22,382 total

includes taxes & fees

Oct 29 - Oct 30

A spacious lobby with a central coffee table, sofas, and a large mirror.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

7. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

P11,181

P13,293 total

includes taxes & fees

Oct 26 - Oct 27

A historic building with ornate architecture, large arched windows, and a prominent Blackstone sign.

A luxurious lobby with a blue sofa, a black entertainment unit, and artwork on the walls.

A grand ballroom with ornate chandeliers, elegant floral centerpieces, and plush seating.

A grand staircase with blue carpet and gold railings leading to a store named 'Mercat'.

8. The Blackstone, Autograph Collection

Downtown Chicago

P15,886

P20,723 total

includes taxes & fees

Oct 25 - Oct 26

View all properties

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good

"Good"

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent

"The room was lovely and clean, breakfast was good, staff was very pleasant"

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent

"Good"

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Rooms very clean. Staff very friendly and helpful… will definitely stay here again"

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