South Side Holiday Rentals, Chicago: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in South Side

Pet friendly

Apartment

Apart hotel

Pool

Condo

Hot tub

Spa

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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 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.

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.

1. Sophy Hyde Park

Hyde Park

amy

Rp6.135.799

Rp7.726.680 total

includes taxes & fees

20 Oct - 21 Oct

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.

2. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Gladys

Rp4.907.925

Rp5.835.031 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 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.

3. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Laura

Rp3.999.513

Rp4.755.022 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 hotel room with a sofa, two armchairs, a coffee table, a TV, and a city view.

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

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

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

Rp3.003.766

Rp3.526.121 total

includes taxes & fees

4 Oct - 5 Oct

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

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

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

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 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.

A modern lobby with a vending machine, a statue, and an exit sign.

7. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Fabian

Rp2.712.744

Rp3.362.960 total

includes taxes & fees

27 Sept - 28 Sept

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.

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

8. Chicago Marriott Midway

Bedford Park

Patricia

Rp4.063.762

Rp4.774.251 total

includes taxes & fees

26 Sept - 27 Sept

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

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

9. Best Western Inn & Suites - Midway Airport

Burbank

David L

Rp2.484.699

Rp2.757.519 total

includes taxes & fees

28 Sept - 29 Sept

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

10. Motel 6 - Chicago, IL

Washington Heights

Nazli

Rp1.598.042

Rp1.875.955 total

includes taxes & fees

5 Oct - 6 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 breakfast bar with coffee makers, a toaster, and a variety of pastries.

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

Icaro

Rp1.859.618

Rp2.183.134 total

includes taxes & fees

23 Sept - 24 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 kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

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.

12. Rainbow Motel

Garfield Ridge

Jerry

Rp1.366.478

Rp1.604.109 total

includes taxes & fees

5 Oct - 6 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 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.

13. Villa Dubois Guest House

Bronzeville

Robert

Rp2.170.916

Rp2.548.438 total

includes taxes & fees

23 Sept - 24 Sept

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.

14. Chinatown Hotel Chicago

Chinatown

Celina

Rp1.451.717

Rp1.704.058 total

includes taxes & fees

23 Sept - 24 Sept

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

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.

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

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

Ashburn

Aniya

Rp1.527.188

Rp1.945.485 total

includes taxes & fees

5 Oct - 6 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 dining area with a wooden table and chairs, a chandelier, and a view into the kitchen.

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

16. Mccormick Place Guest House

Bronzeville

Robert

Rp1.710.314

Rp2.007.736 total

includes taxes & fees

29 Sept - 30 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

Rp1.460.595

Rp1.714.593 total

includes taxes & fees

5 Oct - 6 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 hotel room with a bed, a dresser, a desk, and a mirror.

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

18. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

Rp1.460.595

Rp1.714.593 total

includes taxes & fees

15 Oct - 16 Oct

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Ann

Rp6.631.548

Rp7.884.019 total

includes taxes & fees

7 Oct - 8 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 room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

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

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

20. L7 Chicago by LOTTE

Downtown Chicago

christina

Rp5.098.322

Rp6.061.396 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 Chicago – Midway Airport S by IHG

10/10 Excellent

"amazing and friendly staff"

Motel 6 - Chicago, IL

8/10 Good

"The front office manager was very helpful with a problem that arose back home during my travel. There is ample free parking in an accessible area with several food places within walking distance. My only issue is that the room could have been cleaner and smelled of cigarette smoke. Due to my allergies I cut my stay short - I couldn’t handle the smell anymore. It seems to be a recurring theme with sites booked through Hotels.com that they are not as clean as travelers expect. It doesn’t cost anymore to clean a room in a budget hotel than in a five-star. Perhaps investing in some Mr. Clean Magic Erasers would help!"

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."

Chinatown Hotel Chicago

8/10 Good

"Was a nice place could use some TLC but overall nice and close to the L trains"

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"We had a late arrival"

Villa Dubois Guest House

8/10 Good

"Our stay was pleasant. No issues. The staff communicated as necessary."

Sophy Hyde Park

10/10 Excellent

"Great hotel with an awesome Hyde Park vibe. Would definitely stay there again."

Chicago Lake Shore Hotel

8/10 Good

"The stairs were steep and are difficult for seniors. The air conditioning was really cool."

More cheap stays in South Side

Rainbow Motel

7050 W Archer Ave Chicago IL

Rp1.366.478

Rp1.604.109 total

5 Oct - 6 Oct

includes taxes & fees

5.4/10 (59 reviews)

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Rp1.598.042

Rp1.875.955 total

5 Oct - 6 Oct

includes taxes & fees

7/10 Good! (495 reviews)

Saratoga Motel By Capital O Near Midway Airport Chicago IL

7701, S Cicero Avenue Chicago IL

Rp1.527.188

Rp1.945.485 total

5 Oct - 6 Oct

includes taxes & fees

Carlton Inn Midway

4944 S Archer Ave Chicago IL

Rp1.859.618

Rp2.183.134 total

23 Sept - 24 Sept

includes taxes & fees

6/10 (1,009 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Rp2.712.744

Rp3.362.960 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! (1,375 reviews)

Explore a world of travel with Expedia

Book Hotels in South Side on Expedia.com

Find hotels in South Side, IL from Rp1.604.109

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. Saratoga Motel By Capital O Near Midway Airport Chicago IL

16. Mccormick Place Guest House

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

Holiday Inn Chicago – Midway Airport S by IHG

Motel 6 - Chicago, IL

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

Rainbow Motel

Chinatown Hotel Chicago

Hyatt Place Chicago-South/University Medical Center

Villa Dubois Guest House

Sophy Hyde Park

Chicago Lake Shore Hotel

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

Go further with the Expedia app