Hotels with free parking, South Side Chicago | Expedia

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 Hotels with free parking

Tonight

Oct 15 - Oct 16

Tomorrow

Oct 16 - Oct 17

This weekend

Oct 16 - Oct 18

Next weekend

Oct 23 - Oct 25

Our top choices for South Side hotels with parking

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

A residential street with a sidewalk, houses, and greenery.

1. Carleton of Oak Park

Oak Park

United States

Brad

P7,687

P8,531 total

includes taxes & fees

Oct 21 - Oct 22

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

2. Congress Plaza Hotel

Downtown Chicago

United States

Ashya

P7,291

P8,668 total

includes taxes & fees

Nov 10 - Nov 11

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

3. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

United States

Aran

P7,964

P9,469 total

includes taxes & fees

Nov 9 - Nov 10

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 modern interior with a staircase, green upholstered seating, and artwork on the walls.

A breakfast bar with labeled sections for cereal and fruit, a blue oatmeal container, and a variety of condiments and utensils.

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

Bedford Park

United States

Roberto

P8,489

P9,973 total

includes taxes & fees

Nov 15 - Nov 16

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

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.

A modern multi-story building with a prominent central tower, large windows, and a pedestrian walkway.

5. Hyatt Place Chicago-South/University Medical Center

Hyde Park

United States

Gladys

P11,178

P13,290 total

includes taxes & fees

Nov 1 - Nov 2

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 lobby with a modern design, featuring a large sofa, multiple chairs, a coffee table, and a mural of an airplane.

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

6. Best Western Inn & Suites - Midway Airport

Burbank

United States

David L

P7,129

P7,912 total

includes taxes & fees

Nov 1 - Nov 2

A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.

A bathroom with a marble wall, a bathtub, a toilet, and a shower curtain.

A room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.

A multi-story motel with a parking lot.

7. Motel 6 - Chicago, IL

Washington Heights

Canada

Nazli

P5,651

P6,634 total

includes taxes & fees

Oct 28 - Oct 29

A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.

A modern living room with a grey sofa, a round coffee table, and a chair. There are framed pictures on the wall and a window providing natural light.

A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

8. Carlton Inn Midway

Archer Heights

United States

stephen T

P6,188

P7,264 total

includes taxes & fees

Nov 4 - Nov 5

View all properties

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"James in the Bar was the Best. And the Chicken wings & Fries Lemon pepper i rate a 10 and I own a chicken restaurant"

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent

"Very clean room with working microwave ave fridge. Perfect for a stay close to the city!"

Jaslin Hotel

Jaslin Hotel

10/10 Excellent

"Second time staying at Jaslin for marathon and we will come back."

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