South Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for South Side hotels

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

A modern kitchen with built-in appliances, wooden cabinets, and a variety of food items on shelves.

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

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

1. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Cayci

฿6,307

฿7,498 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

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

Bedford Park

Roberto

฿4,661

฿5,475 total

includes taxes & fees

9 Nov - 10 Nov

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

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

3. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Gladys

฿5,968

฿7,096 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.

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

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.

A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.

4. Sophy Hyde Park

Hyde Park

Mary Kay

฿9,023

฿11,576 total

includes taxes & fees

31 Oct - 1 Nov

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.

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

5. Chicago Marriott Midway

Bedford Park

Carolyn

฿6,002

฿7,051 total

includes taxes & fees

26 Oct - 27 Oct

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 hallway with a patterned carpet, framed artwork on the walls, and a skylight ceiling.

A hotel with multiple floors, large windows, and a prominent sign for the Jaslin Hotel.

6. Jaslin Hotel

Chinatown

Jeffrey

฿6,657

฿7,915 total

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.

7. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

฿4,392

฿5,492 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

8. Best Western Inn & Suites - Midway Airport

Burbank

David L

฿3,806

฿4,224 total

includes taxes & fees

1 Nov - 2 Nov

A row of parked cars along a tree-lined street with multi-story buildings in the background.

9. Chicago Lake Shore Hotel

Kenwood

Princets

฿5,331

฿6,258 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a large bed, a nightstand, a wall-mounted lamp, and a door.

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.

10. Motel 6 - Chicago, IL

Washington Heights

Nazli

฿3,017

฿3,542 total

includes taxes & fees

25 Oct - 26 Oct

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 flat-screen TV mounted above a fireplace, flanked by two potted plants.

A reception area with a wooden reception desk, a sofa, and a coffee table.

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.

11. Carlton Inn Midway

Archer Heights

stephen T

฿3,511

฿4,122 total

includes taxes & fees

13 Oct - 14 Oct

A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.

A dining area with a wooden table and chairs, a rock sculpture centerpiece, and a large green wall art piece.

A room with a wooden herringbone ceiling, a wall clock, and shelves with various decorative items and books.

A neatly made bed with a headboard, two bedside tables with lamps, and a wall-mounted artwork above the bed.

12. Villa Dubois Guest House

Bronzeville

Yohannes

฿4,708

฿5,526 total

includes taxes & fees

1 Nov - 2 Nov

A brick building with a sign for Chicagochinatownhotel.com.

A hallway with two doors, each with a number plate.

A hotel lobby with a black leather sofa, a white armchair, a large vase, and a potted plant.

A dining area with a rectangular table, six chairs, and two windows.

13. Chinatown Hotel Chicago

Chinatown

Jennifer

฿3,054

฿3,585 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a large bed, a flat-screen TV mounted on the ceiling, and a nightstand with a lamp.

A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.

A reception desk with a glass partition, a no pets allowed sign, a no smoking sign, a QR code for check-in, and a sign indicating a 1-minute wait for guests.

14. Rainbow Motel

Garfield Ridge

Jerry

฿2,342

฿2,750 total

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a dark blue sofa, a glass coffee table, and a wooden log wall.

A modern kitchen with dark cabinetry, a stainless steel stove, and a glass-fronted upper cabinet.

A modern living room with a fireplace, two armchairs, a sofa, and a large plant.

A bedroom with a large bed, a headboard, a wall-mounted artwork, and a window with curtains.

15. Mccormick Place Guest House

Bronzeville

Tyler

฿3,213

฿3,772 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.

A reception desk with various notices and a security camera.

A motel with a row of parking spaces and a building with a red roof and beige walls.

16. Saratoga Motel By Capital O Near Midway Airport Chicago IL

Ashburn

Aniya

฿2,884

฿3,673 total

includes taxes & fees

12 Oct - 13 Oct

A room with large windows, a wooden floor, and a built-in air conditioning unit.

A hotel room with a large bed, a wooden headboard, a patterned bedspread, and a view through an open door to another room.

17. Best Motel By OYO Chicago I-90

Woodlawn

Saul

฿2,758

฿3,237 total

includes taxes & fees

25 Oct - 26 Oct

A multi-story building with a brick facade, multiple windows, and a covered walkway.

A hallway with a glass door, a window with a view of the outside, and a ceiling-mounted air conditioning unit.

A hotel room with a bed, a dresser, a desk, and a mirror.

A bathroom with a toilet, sink, and bathtub.

18. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

฿2,758

฿3,237 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

฿6,084

฿7,232 total

includes taxes & fees

29 Oct - 30 Oct

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

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

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.

20. Hotel 505 River North

Downtown Chicago

Giana

฿6,337

฿8,608 total

includes taxes & fees

8 Nov - 9 Nov

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Stay near popular South Side attractions

A cityscape with historic buildings, a prominent church, and a view of the ocean.

University of Chicago

8.6/10 (3,689 reviews)

Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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A baseball stadium with advertisements, including 'xfinity' and 'proven IT'.

Rate Field

8.6/10 (235 reviews)

Catch an event at Rate Field during your trip to Chicago. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

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A classical building with a dome and columns, featuring Charlie Brown exhibit banners.

Griffin Museum of Science and Industry

9.2/10 (1,796 reviews)

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

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A train passing through a tunnel with a curved roof and string lights.

Illinois Institute of Technology

7.0/10 (4 reviews)

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

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A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Jackson Park

7.4/10 (9 reviews)

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

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Rainbow Beach

Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.

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Obama Presidential Center

You can spend an afternoon browsing the exhibits at Obama Presidential Center in Chicago. Wander the beaches and gardens while you're in the area.

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Wabash Ave YMCA

You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan.

See all hotels in South Side

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."

Motel 6 - Chicago, IL

10/10 Excellent

"It was a decent motel for the price."

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."

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Room was clean, spacious bathroom. Breakfast was great."

Admiral Motel By Oyo Chicago I-94

10/10 Excellent

"Air conditioner was broken, toilet was leaking from the floor, but staff, guests and neighbours were very friendly. Overall good given the affordable cost. Not a five star hotel, but doesn’t pretend to be"

More cheap stays in South Side

Rainbow Motel

7050 W Archer Ave Chicago IL

฿2,342

฿2,750 total

14 Oct - 15 Oct

includes taxes & fees

Best Motel By OYO Chicago I-90

6535 S King Dr Chicago IL

฿2,758

฿3,237 total

25 Oct - 26 Oct

includes taxes & fees

3.6/10 (152 reviews)

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

฿3,017

฿3,542 total

25 Oct - 26 Oct

includes taxes & fees

7/10 Good! (509 reviews)

Carlton Inn Midway

4944 S Archer Ave Chicago IL

฿3,511

฿4,122 total

13 Oct - 14 Oct

includes taxes & fees

5.8/10 (1,009 reviews)

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

6500 S Cicero Ave Chicago IL

฿4,661

฿5,475 total

9 Nov - 10 Nov

includes taxes & fees

9/10 Wonderful! (1,374 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

฿4,392

฿5,492 total

8 Nov - 9 Nov

includes taxes & fees

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More ways to book

Book Hotels in South Side on Expedia.com

Find hotels in South Side, IL from ฿2,750

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in South Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for South Side hotels

1. SpringHill Suites by Marriott Chicago Chinatown

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

3. Hyatt Place Chicago-South/University Medical Center

4. Sophy Hyde Park

5. Chicago Marriott Midway

6. Jaslin Hotel

7. Holiday Inn Chicago – Midway Airport S by IHG

8. Best Western Inn & Suites - Midway Airport

9. Chicago Lake Shore Hotel

10. Motel 6 - Chicago, IL

11. Carlton Inn Midway

12. Villa Dubois Guest House

13. Chinatown Hotel Chicago

14. Rainbow Motel

15. Mccormick Place Guest House

16. Saratoga Motel By Capital O Near Midway Airport Chicago IL

17. Best Motel By OYO Chicago I-90

18. Admiral Motel By Oyo Chicago I-94

19. Hilton Vacation Club Hotel Blake Chicago

20. Hotel 505 River North

Stay near popular South Side attractions

University of Chicago

Rate Field

Griffin Museum of Science and Industry

Illinois Institute of Technology

Jackson Park

Rainbow Beach

Obama Presidential Center

Wabash Ave YMCA

Learn more about South Side

Top South Side Hotel Reviews

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

Motel 6 - Chicago, IL

Carlton Inn Midway

Chicago Lake Shore Hotel

SpringHill Suites by Marriott Chicago Chinatown

Admiral Motel By Oyo Chicago I-94

More cheap stays in South Side

Rainbow Motel

Best Motel By OYO Chicago I-90

Motel 6 - Chicago, IL

Carlton Inn Midway

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

Holiday Inn Chicago – Midway Airport S by IHG

Explore a world of travel with Expedia

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