TOP Hotels with Parking in South Side, IL for 2026

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Check availability on South Side Hotels with Parking

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Our top choices for South Side hotels with parking

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

1. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

£163

includes taxes & fees

29 Oct - 30 Oct

A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.

A modern restaurant with a bar area, multiple seating options, and a contemporary design.

A modern lobby with a sofa, a coffee table, and a large digital art display.

A modern hotel room with a bed, a sofa, a desk, and artwork on the walls.

2. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Cayci

£169

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.

A hotel reception desk with a modern design, including a digital display and a sign indicating it is a non-smoking property.

3. Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Bedford Park

Roberto

£123

includes taxes & fees

11 Nov - 12 Nov

An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.

A hotel room with a bed, a desk, a chair, a sofa, a coffee table, and a painting on the wall.

A restaurant with a bar area, seating, and a television screen displaying a sports event.

A modern lounge area with a fireplace, comfortable seating, and a large window.

4. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Gladys

£160

includes taxes & fees

1 Nov - 2 Nov

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

5. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

£124

includes taxes & fees

8 Nov - 9 Nov

A modern living room with two grey armchairs, a round coffee table, and a large potted plant.

A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.

A hotel room with two beds, a desk, and a chair.

6. Chicago Marriott Midway

Bedford Park

Carolyn

£159

includes taxes & fees

26 Oct - 27 Oct

A hotel lobby with a reception desk, seating area, and a cityscape mural on the ceiling.

A hotel room with a large bed, two bedside tables with lamps, a leather armchair, a sofa, and a small table.

A spacious hotel lobby with seating areas, a reception desk, and a large window offering a view.

A Best Western hotel with a brick facade, multiple windows, and a covered parking area.

7. Best Western Inn & Suites - Midway Airport

Burbank

David L

£95

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk, a chair, a nightstand, a lamp, and a mirror.

8. Chicago Lake Shore Hotel

Kenwood

Princets

£141

includes taxes & fees

1 Nov - 2 Nov

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Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"Jill at the desk is the best! She goes above and beyond for guests, so kind and helpful."

Carlton Inn Midway

8/10 Good

"Excellent staff. Very clean outside. Good breakfast. Coffee in office 24/7-which was wonderful. No elevator but only 2 floors."

Chicago Lake Shore Hotel

10/10 Excellent

"Definitely a motel vibe, no elevator. Nice staff and clean rooms."

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Check availability on South Side Hotels with Parking

Our top choices for South Side hotels with parking

1. Hilton Vacation Club Hotel Blake Chicago

2. SpringHill Suites by Marriott Chicago Chinatown

3. Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

4. Hyatt Place Chicago-South/University Medical Center