TOP Luxury Hotels in South Side for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels | Expedia Singapore

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

Tonight

29 Sept - 30 Sept

Tomorrow

30 Sept - 1 Oct

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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 spacious living area with a modern chandelier, comfortable seating, and a fireplace.

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

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.

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.

S$464

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

2. Hilton Chicago

Downtown Chicago

S$289

includes taxes & fees

30 Oct - 31 Oct

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

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

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

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

3. The Wade

Downtown Chicago

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

S$226

includes taxes & fees

25 Oct - 26 Oct

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

A balcony with a glass railing, a table, and four chairs.

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

4. Sentral Michigan Avenue

Downtown Chicago

S$300

includes taxes & fees

26 Oct - 27 Oct

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

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

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

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

5. Hyatt Centric The Loop Chicago

Downtown Chicago

S$441

includes taxes & fees

29 Oct - 30 Oct

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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

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

S$457

includes taxes & fees

29 Oct - 30 Oct

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

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

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

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

7. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

S$272

includes taxes & fees

27 Oct - 28 Oct

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

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

8. The Blackstone, Autograph Collection

Downtown Chicago

S$423

includes taxes & fees

25 Oct - 26 Oct

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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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