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

Historic Hotels & Resorts in South Side from NZ$388

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Check availability on South Side Historic Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for South Side historic hotels

A large, historic building with a central courtyard surrounded by trees.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
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

Hilton Chicago
Downtown Chicago
United States
Alan
NZ$388
includes taxes & fees
24 Oct - 25 Oct
Hilton Chicago
The Intercontinental hotel facade with a large American flag and a floral display.
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 lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

2. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
United States
Kenan
NZ$579
includes taxes & fees
25 Oct - 26 Oct
InterContinental Chicago Magnificent Mile by IHG
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.
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.
A hallway with a wicker shelf holding towels and toiletries, a framed Arabic calligraphy piece, and a wooden door leading to a bathroom.

3. A quiet stay while you are away

A quiet stay while you are away
Oak Park
United States
Fred D.
A quiet stay while you are away
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.
A bedroom with a bed, a window with a view of a brick wall, a ceiling fan, and a framed picture on the wall.
A modern living room with a sofa, coffee table, and a kitchen area with a refrigerator and bar stools.
A modern kitchen with stainless steel appliances, wooden cabinets, and a green tiled backsplash.

4. Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Lakeview
United States
Enrique
NZ$1,855
includes taxes & fees
14 Oct - 15 Oct
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
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

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Lakeview
United States
Meaghan M.
NZ$1,855
includes taxes & fees
14 Oct - 15 Oct
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.
A grand hall with a central aisle, ornate chandeliers, and rows of chairs.
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

6. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
Gabriella
NZ$571
includes taxes & fees
25 Oct - 26 Oct
Palmer House a Hilton Hotel
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Top South Side Hotel Reviews

Chicago Lake Shore Hotel

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."
Jesse 3-night trip
Posted 9 hours ago
Chicago Lake Shore Hotel
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"location is fantastic, staff very helpful, traveled with my pet and no issues whatsoever."
Denise 3-night trip
Posted 2 days ago
Hyatt Place Chicago-South/University Medical Center
Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Excellent breakfast, best shuttle service, Excellent hospitality."
Amit 1-night trip
Posted 8 days ago
Carlton Inn Midway

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