South Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for South Side hotels

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

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.

1. Sophy Hyde Park

Hyde Park

amy

Rp5.536.886

Rp7.024.646 total

includes taxes & fees

24 Oct - 25 Oct

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.

2. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Denise

Rp4.918.100

Rp5.847.128 total

includes taxes & fees

23 Oct - 24 Oct

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

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

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

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

3. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Wenli

Rp4.007.804

Rp4.764.877 total

includes taxes & fees

23 Oct - 24 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 with multiple floors, large windows, and a prominent sign for the Jaslin Hotel.

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

4. Jaslin Hotel

Chinatown

Jeffrey

Rp3.058.619

Rp3.636.148 total

includes taxes & fees

29 Sept - 30 Sept

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

5. Chicago Lake Shore Hotel

Kenwood

John

Rp3.018.820

Rp3.543.794 total

includes taxes & fees

24 Sept - 25 Sept

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 conference room with a long table, yellow chairs, and water bottles.

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

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

Bedford Park

Beatrice

Rp3.212.460

Rp3.773.997 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

7. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Fabian

Rp2.718.368

Rp3.369.933 total

includes taxes & fees

27 Sept - 28 Sept

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.

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

8. Chicago Marriott Midway

Bedford Park

Carolyn

Rp3.523.148

Rp4.138.995 total

includes taxes & fees

24 Oct - 25 Oct

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

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

9. Best Western Inn & Suites - Midway Airport

Burbank

David L

Rp2.497.152

Rp2.771.339 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Rp1.606.052

Rp1.885.357 total

includes taxes & fees

6 Oct - 7 Oct

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

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.

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

11. Carlton Inn Midway

Archer Heights

Icaro

Rp1.868.938

Rp2.194.078 total

includes taxes & fees

24 Sept - 25 Sept

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 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.

A compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

12. Rainbow Motel

Garfield Ridge

Jerry

Rp1.373.327

Rp1.612.120 total

includes taxes & fees

24 Sept - 25 Sept

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

A modern kitchen with white cabinets, stainless steel appliances, and patterned wallpaper.

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

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

13. Villa Dubois Guest House

Bronzeville

Robert

Rp2.181.796

Rp2.561.210 total

includes taxes & fees

24 Sept - 25 Sept

A brick building with a sign for Chicagochinatownhotel.com.

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

A reception area with a wooden desk, a black leather sofa, and a wall with 'CHINATOWN HOTEL' signage.

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

14. Chinatown Hotel Chicago

Chinatown

Celina

Rp1.807.008

Rp2.121.249 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

15. Mccormick Place Guest House

Bronzeville

Tyler

Rp1.710.314

Rp2.007.736 total

includes taxes & fees

24 Sept - 25 Sept

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 room with a microwave on a counter, a door with a 'No Smoking' sign, and a window with a view of cars and trees.

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

Ashburn

Aniya

Rp1.534.842

Rp1.955.234 total

includes taxes & fees

24 Sept - 25 Sept

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

Rp1.467.916

Rp1.723.128 total

includes taxes & fees

6 Oct - 7 Oct

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

A brick building with a sign for the Admiral Motel.

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

A bathroom with a toilet, sink, and bathtub.

18. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

Rp1.470.959

Rp1.726.759 total

includes taxes & fees

7 Oct - 8 Oct

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

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

A modern bathroom with a dual sink vanity, a large mirror, and a toilet.

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

Rp5.636.796

Rp6.701.588 total

includes taxes & fees

14 Oct - 15 Oct

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

20. L7 Chicago by LOTTE

Downtown Chicago

GUILLERMO

Rp5.123.874

Rp6.091.773 total

includes taxes & fees

27 Sept - 28 Sept

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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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Barack Obama Residence

You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

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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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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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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

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Rooms very clean. Staff very friendly and helpful… will definitely stay here again"

Chicago Marriott Midway

10/10 Excellent

"Great experience"

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Good location, safe, convenient, clean"

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"location is fantastic, staff very helpful, traveled with my pet and no issues whatsoever."

Chicago Lake Shore Hotel

10/10 Excellent

"My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!"

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"amazing and friendly staff"

Sophy Hyde Park

10/10 Excellent

"XXX"

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

10/10 Excellent

"Staff was very accommodating. The breakfast was ok."

Rainbow Motel

10/10 Excellent

"Good Location with plenty of walkable places. Lots of restaurants and stores nearby which is always a plus. No microwave in the room but the mini fridge worked wonderfully. Lots of options on the TV as well. Staff was very nice and welcoming. Overall a very nice experience. Very good option for anyone looking for a more affordable option. Would definitely recommend."

More cheap stays in South Side

Rainbow Motel

7050 W Archer Ave Chicago IL

Rp1.373.327

Rp1.612.120 total

24 Sept - 25 Sept

includes taxes & fees

5.4/10 (60 reviews)

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Rp1.606.052

Rp1.885.357 total

6 Oct - 7 Oct

includes taxes & fees

Saratoga Motel By Capital O Near Midway Airport Chicago IL

7701, S Cicero Avenue Chicago IL

Rp1.534.842

Rp1.955.234 total

24 Sept - 25 Sept

includes taxes & fees

Carlton Inn Midway

4944 S Archer Ave Chicago IL

Rp1.868.938

Rp2.194.078 total

24 Sept - 25 Sept

includes taxes & fees

6/10 (1,010 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Rp2.718.368

Rp3.369.933 total

27 Sept - 28 Sept

includes taxes & fees

8/10 Very good! (1,014 reviews)

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

6500 S Cicero Ave Chicago IL

Rp3.212.460

Rp3.773.997 total

27 Sept - 28 Sept

includes taxes & fees

9/10 Wonderful! (1,369 reviews)

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Book Hotels in South Side on Expedia.com

Find hotels in South Side, IL from Rp1.612.120

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. Sophy Hyde Park

2. Hyatt Place Chicago-South/University Medical Center

3. SpringHill Suites by Marriott Chicago Chinatown

4. Jaslin Hotel

5. Chicago Lake Shore Hotel

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

7. Holiday Inn Chicago – Midway Airport S by IHG

8. Chicago Marriott Midway

9. Best Western Inn & Suites - Midway Airport

10. Motel 6 - Chicago, IL

11. Carlton Inn Midway

12. Rainbow Motel

13. Villa Dubois Guest House

14. Chinatown Hotel Chicago

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. L7 Chicago by LOTTE

Stay near popular South Side attractions

University of Chicago

Rate Field

Griffin Museum of Science and Industry

Illinois Institute of Technology

Jackson Park

Barack Obama Residence

Obama Presidential Center

Rainbow Beach

Learn more about South Side

Top South Side Hotel Reviews

Best Western Inn & Suites - Midway Airport

Chicago Marriott Midway

SpringHill Suites by Marriott Chicago Chinatown

Hyatt Place Chicago-South/University Medical Center

Chicago Lake Shore Hotel

Holiday Inn Chicago – Midway Airport S by IHG

Sophy Hyde Park

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

Rainbow Motel

More cheap stays in South Side

Rainbow Motel

Motel 6 - Chicago, IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

Carlton Inn Midway

Holiday Inn Chicago – Midway Airport S by IHG

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

Explore a world of travel with Expedia

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