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

Hotels with free parking in South Side

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Check availability on South Side Hotels with free parking

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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

Carleton of Oak Park
Oak Park
United States
Brad
S$174
includes taxes & fees
27 Oct - 28 Oct
Carleton of Oak Park
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

Congress Plaza Hotel
Downtown Chicago
United States
Ashya
S$163
includes taxes & fees
10 Nov - 11 Nov
Congress Plaza Hotel
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.
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.

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
S$193
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown South Loop
A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.
A modern interior with a staircase, green upholstered seating, and artwork on the walls.
A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Roberto
S$204
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.
A modern multi-story building with a prominent central tower, large windows, and a pedestrian 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.

5. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
S$271
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago-South/University Medical Center
A hotel lobby with a reception desk, seating area, and a cityscape mural on the ceiling.
A Best Western hotel with a brick facade, multiple windows, and a covered parking area.
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.

6. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
Burbank
United States
David L
S$161
includes taxes & fees
1 Nov - 2 Nov
Best Western Inn & Suites - Midway Airport
A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.
A multi-story motel with a parking lot.
A room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.
A bathroom with a marble wall, a bathtub, a toilet, and a shower curtain.

7. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
Washington Heights
Canada
Nazli
S$135
includes taxes & fees
28 Oct - 29 Oct
Motel 6 - Chicago, IL
A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.
A breakfast bar with coffee makers, a toaster, and a variety of pastries.
A reception area with a wooden reception desk, a sofa, and a coffee table.
A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

8. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
stephen T
S$161
includes taxes & fees
18 Oct - 19 Oct
Carlton Inn Midway
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A modern lobby with a vending machine, a statue, and an exit sign.
A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.
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.

9. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
S$216
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Chicago – Midway Airport S by IHG
Interior entrance
Bathroom
Exterior
A hotel room with a large bed, a desk, a chair, a nightstand, a lamp, and a mirror.

10. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
Kenwood
United States
Princets
S$239
includes taxes & fees
3 Nov - 4 Nov
Chicago Lake Shore Hotel
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"
Kenyatta J 1-night trip
Posted 6 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
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!"
Nicole 1-night trip
Posted 13 hours ago
Chicago Lake Shore Hotel
Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Second time staying at Jaslin for marathon and we will come back."
Omar r ramos 5-night trip
Posted 15 hours ago
Jaslin Hotel

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