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

Find South Side Hotels with Shuttle Services from S$149

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your current months are November, 2026 and December, 2026.

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Our top choices for South Side hotels with transport

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

A modern conference room with a wooden table, white chairs, a potted plant, and a large window with decorative plants.

1. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

4.0 star property

Downtown Chicago

9.6 out of 10, Exceptional, (1,220 reviews)

9.6/10

Exceptional

(1,220 reviews)

"Great location from both airports. Lovely hotel clean and convenient"

Kanokkan

The price is S$170

S$170

includes taxes & fees

9 Dec - 10 Dec

Hilton Vacation Club Hotel Blake Chicago

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

SpringHill Suites by Marriott Chicago Chinatown

3.5 star property

Chinatown

9.6 out of 10, Exceptional, (1,007 reviews)

9.6/10

Exceptional

(1,007 reviews)

"Nice and convenient location, with nice breakfast and friendly staff."

Shouan

The price is S$150

S$150

includes taxes & fees

7 Dec - 8 Dec

SpringHill Suites by Marriott Chicago Chinatown

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

3. Hotel 505 River North

Hotel 505 River North

4.5 star property

Downtown Chicago

9.2 out of 10, Wonderful, (3,009 reviews)

9.2/10

Wonderful

(3,009 reviews)

"Great stay!"

Miya

The price is S$236

S$236

includes taxes & fees

9 Dec - 10 Dec

Hotel 505 River North

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

A hotel entrance with a glass door, a number 6500 sign above, and two signs indicating courtesy shuttle pick-up only.

A hotel reception area with a modern design, including a reception desk, a digital display, and a dining area with tables and chairs.

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

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

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

2.5 star property

Bedford Park

9.0 out of 10, Wonderful, (1,385 reviews)

9.0/10

Wonderful

(1,385 reviews)

"Easy parking, clean room & good breakfast."

Christopher

The price is S$185

S$185

includes taxes & fees

6 Dec - 7 Dec

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

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

A modern hotel with a corner location, large windows, and a green awning.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

5. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown

3.0 star property

Downtown Chicago

9.2 out of 10, Wonderful, (1,593 reviews)

9.2/10

Wonderful

(1,593 reviews)

"Great hotel"

Tracy

The price is S$153

S$153

includes taxes & fees

8 Dec - 9 Dec

Hampton Inn & Suites Chicago Downtown

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

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.

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

6. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3.0 star property

Hyde Park

8.8 out of 10, Excellent, (1,010 reviews)

8.8/10

Excellent

(1,010 reviews)

"Rooms were very clean and breakfast was actually pretty good."

Kelley

The price is S$232

S$232

includes taxes & fees

22 Nov - 23 Nov

Hyatt Place Chicago-South/University Medical Center

An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.

A spacious living area with a modern chandelier, comfortable seating, and a fireplace.

A modern living room with a marble column, wooden shelves, and a unique chandelier.

A bar area with a marble countertop, multiple shelves of bottles, and a large TV screen. There are several bar stools and a round table with a vase of flowers.

7. Sophy Hyde Park

Sophy Hyde Park

4.0 star property

Hyde Park

9.4 out of 10, Exceptional, (1,006 reviews)

9.4/10

Exceptional

(1,006 reviews)

"The staff was wonderful. Very knowledgable and always pleasant."

Eva

The price is S$351

S$351

includes taxes & fees

23 Nov - 24 Nov

Sophy Hyde Park

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

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

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

8. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 star property

West Lawn

8.0 out of 10, Very good, (1,005 reviews)

8.0/10

Very good

(1,005 reviews)

"The staff was really kind and helpful!"

Dorsy

The price is S$160

S$160

includes taxes & fees

6 Dec - 7 Dec

Holiday Inn Chicago – Midway Airport S by IHG

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

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

A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

9. Chicago Marriott Midway

Chicago Marriott Midway

3.5 star property

Bedford Park

8.4 out of 10, Very good, (1,004 reviews)

8.4/10

Very good

(1,004 reviews)

"Overall great stay"

Cynitha

The price is S$215

S$215

includes taxes & fees

22 Nov - 23 Nov

Chicago Marriott Midway

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

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

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.

10. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

3.0 star property

Burbank

7.0 out of 10, Good, (1,000 reviews)

7.0/10

Good

(1,000 reviews)

"Always visit this location when we’re in the city. Can’t help but love them , especially the breakfast!! Best bacon ever"

William

The price is S$149

S$149

includes taxes & fees

1 Dec - 2 Dec

Best Western Inn & Suites - Midway Airport

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top South Side Hotel Reviews

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

For the price, great quality in rooms, check in and nearby food options.

Rahul

Reviewed March 30, 2024Reviewed March 30, 2024

Hilton Vacation Club Hotel Blake Chicago

Sophy Hyde Park

Hyde Park

10/10 Excellent

Return to the same property after my first visit. It is a very decent hotel although abit costly due to the DNC in Chicago. Will stay again!

Yun Jie Serene

Reviewed September 1, 2024Reviewed September 1, 2024

Sophy Hyde Park

A hotel room with a large window offering a city view, two armchairs, a bed, and a lamp.

A modern lobby with a glass partition, a fireplace, and a seating area.

A hotel room with a sofa, two armchairs, a coffee table, a TV, and a city view.

Jaslin Hotel

Chinatown

10/10 Excellent

Jaslin hotel is located at a convenient location surrounded by Asian eateries. It’s close to bus and subway stops. The staff was most helpful although the phone in the room doesn’t work

Pyng

Reviewed October 24, 2025Reviewed October 24, 2025

Jaslin Hotel

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

Chicago Lake Shore Hotel

Kenwood

10/10 Excellent

This was needed for a loss in the family so it was fine

Jermaine

Reviewed August 30, 2020Reviewed August 30, 2020

Chicago Lake Shore Hotel

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Find South Side Hotels with Shuttle Services from S$149

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side hotels with transport

1. Hilton Vacation Club Hotel Blake Chicago

2. SpringHill Suites by Marriott Chicago Chinatown

3. Hotel 505 River North

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

5. Hampton Inn & Suites Chicago Downtown

6. Hyatt Place Chicago-South/University Medical Center

7. Sophy Hyde Park

8. Holiday Inn Chicago – Midway Airport S by IHG

9. Chicago Marriott Midway

10. Best Western Inn & Suites - Midway Airport

Top South Side Hotel Reviews

Hilton Vacation Club Hotel Blake Chicago

10/10 Excellent

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