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.

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Pet friendly

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Pool

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Spa

Hot tub

Family friendly

Cottage

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Our top choices for South Side hotels

Pet-friendly

Reserve now, pay later

Breakfast included

Hotel

Bed & breakfast

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.

1. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Michelle

฿5,267

฿6,262 total

includes taxes & fees

1 Sept - 2 Sept

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.

2. Sophy Hyde Park

Hyde Park

Anna

฿6,772

฿8,910 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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

Bedford Park

Darryl

฿5,660

฿6,649 total

includes taxes & fees

30 Aug - 31 Aug

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

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.

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

4. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Brianna

฿5,270

฿6,266 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

5. Jaslin Hotel

Chinatown

Bart

฿5,252

฿6,245 total

includes taxes & fees

30 Aug - 31 Aug

6. Chicago Lake Shore Hotel

Kenwood

Vanessa

฿5,529

฿6,491 total

includes taxes & fees

7 Sept - 8 Sept

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

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.

7. Chicago Marriott Midway

Bedford Park

Don

฿6,145

฿7,220 total

includes taxes & fees

8 Sept - 9 Sept

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

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

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.

8. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Diane

฿3,726

฿4,701 total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

9. Villa Dubois Guest House

Bronzeville

Steven

฿4,583

฿5,379 total

includes taxes & fees

29 Aug - 30 Aug

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

10. Best Western Inn & Suites - Midway Airport

Burbank

Arlene

฿4,286

฿4,757 total

includes taxes & fees

2 Sept - 3 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 room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.

11. Motel 6 - Chicago, IL

Washington Heights

Diana

฿2,500

฿2,935 total

includes taxes & fees

8 Sept - 9 Sept

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 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.

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

12. Carlton Inn Midway

Archer Heights

Sathya

฿3,423

฿4,018 total

includes taxes & fees

31 Aug - 1 Sept

A brick building with a sign for Chicagochinatownhotel.com.

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

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

13. Chinatown Hotel Chicago

Chinatown

Sydney

฿3,972

฿4,662 total

includes taxes & fees

30 Aug - 31 Aug

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

14. Rainbow Motel

Garfield Ridge

Noel

฿2,515

฿2,953 total

includes taxes & fees

27 Aug - 28 Aug

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

15. Mccormick Place Guest House

Bronzeville

Arely

฿3,133

฿3,677 total

includes taxes & fees

30 Aug - 31 Aug

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

16. Best Motel By OYO Chicago I-90

Woodlawn

Saul

฿2,689

฿3,156 total

includes taxes & fees

17 Sept - 18 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 reception desk with various notices and a security camera.

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

Ashburn

Roseanne

฿2,811

฿3,581 total

includes taxes & fees

31 Aug - 1 Sept

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

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

A bathroom with a toilet, sink, and bathtub.

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

฿2,689

฿3,156 total

includes taxes & fees

8 Sept - 9 Sept

A hotel entrance with a marquee and string lights above the entrance.

A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.

A hotel entrance with a marquee, American flag, and a person standing in front.

19. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

฿5,256

฿6,248 total

includes taxes & fees

1 Sept - 2 Sept

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

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

Girivasan

฿7,037

฿8,366 total

includes taxes & fees

30 Aug - 31 Aug

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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 acclaimed art galleries 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 acclaimed theatre scene and fascinating museums 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 fascinating museums and acclaimed art galleries 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 acclaimed art galleries.

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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 beautiful beaches 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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Bridgeport Art Center

Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant 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

Jaslin Hotel

8/10 Good

"Did not see an ice machine in the hall way. No microwave in the room."

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"Room was nice and clean. Bed was super comfy. Just wished the cafe was open longer than just for breakfast."

Carlton Inn Midway

10/10 Excellent

"Good to stay and staff were good"

Villa Dubois Guest House

10/10 Excellent

"Very nice place BUT… be careful with this place ! I booked this through Expedia and no where does it even mention a $300 deposit!! I paid for my accommodations in full while driving through the US. It wasn't until We arrived at the location I get notice of a Deposit Required before they would let us in or even give us the room number… They WILL NOT TALK WITH YOU ON THE PHONE… text only 🙄 finally i had to send proof of ID to prove I was from another country and it was only after I emailed my drivers license that they “waived” the deposit since we were classified as International Guests. Other than that “ hiccup “ then we were finally allowed to enter the property. Nicely decorated, clean and fairly close to the things we wanted to see and do."

Sophy Hyde Park

8/10 Good

"Nice eclectic hotel in Hyde Park. Lots of meter regulated street parking available after 7pm. Rooms are nice and cozy, however paper thin walls. Carpet in the lobby and rooms need steam cleaning. Housekeeping personnel were very nice. Messler/ Food and drinks from Messler were very tasty and the staff was nice."

Mccormick Place Guest House

10/10 Excellent

"Clean"

Saratoga Motel By Capital O Near Midway Airport Chicago IL

8/10 Good

"Staff was pleasant to me and my service animal. The toiled overflowed as I was about to checkout and towels were stained. I let manager know. Other than that, no issues."

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

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

฿2,500

฿2,935 total

8 Sept - 9 Sept

includes taxes & fees

Best Motel By OYO Chicago I-90

6535 S King Dr Chicago IL

฿2,689

฿3,156 total

17 Sept - 18 Sept

includes taxes & fees

Saratoga Motel By Capital O Near Midway Airport Chicago IL

7701, S Cicero Avenue Chicago IL

฿2,811

฿3,581 total

31 Aug - 1 Sept

includes taxes & fees

6/10 (90 reviews)

Carlton Inn Midway

4944 S Archer Ave Chicago IL

฿3,423

฿4,018 total

31 Aug - 1 Sept

includes taxes & fees

6/10 (1,017 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

฿3,726

฿4,701 total

8 Sept - 9 Sept

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

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

6500 S Cicero Ave Chicago IL

฿5,660

฿6,649 total

30 Aug - 31 Aug

includes taxes & fees

Explore a world of travel with Expedia

More ways to book

Book Hotels in South Side on Expedia.com

Find hotels in South Side, IL from ฿2,935

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. Hyatt Place Chicago-South/University Medical Center

2. Sophy Hyde Park

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

4. SpringHill Suites by Marriott Chicago Chinatown

5. Jaslin Hotel

6. Chicago Lake Shore Hotel

7. Chicago Marriott Midway

8. Holiday Inn Chicago – Midway Airport S by IHG

9. Villa Dubois Guest House

10. Best Western Inn & Suites - Midway Airport

11. Motel 6 - Chicago, IL

12. Carlton Inn Midway

13. Chinatown Hotel Chicago

14. Rainbow Motel

15. Mccormick Place Guest House

16. Best Motel By OYO Chicago I-90

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

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

Bridgeport Art Center

Learn more about South Side

Top South Side Hotel Reviews

Jaslin Hotel

Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Villa Dubois Guest House

Sophy Hyde Park

Mccormick Place Guest House

Saratoga Motel By Capital O Near Midway Airport Chicago IL

Admiral Motel By Oyo Chicago I-94

More cheap stays in South Side

Motel 6 - Chicago, IL

Best Motel By OYO Chicago I-90

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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