TOP Historic Hotels in South Side, IL for 2026

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

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Our top choices for South Side historic hotels

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.

1. Hilton Chicago

Downtown Chicago

Alan

£170

includes taxes & fees

23 Oct - 24 Oct

The Intercontinental hotel facade with a large American flag and a floral display.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

A person sitting by a window with a cityscape view.

2. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Kenan

£248

includes taxes & fees

25 Oct - 26 Oct

A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

A dining room with a wooden table, chairs, a chandelier, and a china cabinet.

A room with a wooden door, large windows with curtains, a table with a yellow tablecloth, and various potted plants.

A spacious living room with a wooden floor, a patterned rug, and a dining area with a chandelier.

3. A quiet stay while you are away

Oak Park

Fred D.

£235

includes taxes & fees

17 Oct - 18 Oct

A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

A modern living room with a sofa, coffee table, and a kitchen area with a refrigerator and bar stools.

A neatly made bed with white linens, a framed picture on the wall, a window with a brick pattern, and a television mounted on the wall.

A bedroom with a bed, a window with a view of a brick wall, a ceiling fan, and a framed picture on the wall.

4. Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Lakeview

Enrique

£799

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with stainless steel appliances, a granite countertop, and a wine bottle.

A modern living room with a fireplace, a flat-screen TV, and a large window offering a view of the outside.

A bedroom with a bed, a nightstand, a framed picture, and a door.

A bathroom with two sinks, a large mirror, and a towel rack with folded towels.

5. Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

Lakeview

Meaghan M.

£813

includes taxes & fees

27 Sept - 28 Sept

A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

A grand hall with a central aisle, ornate chandeliers, and rows of chairs.

6. Palmer House a Hilton Hotel

Downtown Chicago

Gabriella

£245

includes taxes & fees

25 Oct - 26 Oct

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Top South Side Hotel Reviews

Chicago Lake Shore Hotel

10/10 Excellent

"I'll keep it straight forward. The staff was friendly and helpful. The room was clean and simple with refrigerator, microwave and coffee maker. Good house keeping each day. King size bed had a firm mattress that was fairly comfortable but the pillows were so so. The air-conditioning was good. The only downside I found was the shower water pressure was very low but it got the job done so not really a big deal. Over all a good place to stay at a great price."