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

South Side Hotel Guide - Historic Hotels in South Side, Chicago

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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 marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
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
€194
includes taxes & fees
24 Oct - 25 Oct
Hilton Chicago
The Intercontinental hotel facade with a large American flag and a floral display.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
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
€289
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 spacious living room with a wooden floor, a patterned rug, and a dining area with a chandelier.
A room with a wooden door, large windows with curtains, a table with a yellow tablecloth, and various potted plants.
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 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 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
€942
includes taxes & fees
5 Oct - 6 Oct
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
A modern kitchen with stainless steel appliances, a granite countertop, and a wine bottle.
A bedroom with two beds, a window with blinds, a framed photo on the wall, and a bedside table with a cup.
A bathroom with two sinks, a large mirror, and a towel rack with folded towels.
A bedroom with a bed, a nightstand, a framed picture, and a door.

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

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Lakeview
United States
Meaghan M.
€955
includes taxes & fees
27 Sept - 28 Sept
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
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.
A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

6. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
Gabriella
€287
includes taxes & fees
25 Oct - 26 Oct
Palmer House a Hilton Hotel
View all properties

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 8 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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