Far Southeast Side Holiday Rentals, Chicago: Private House Rentals

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Go beyond your typical stay in Far Southeast Side

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Our top choices for Far Southeast Side hotels

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 brick building with a sign for the Admiral Motel.

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

1. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

฿2,749

฿3,227 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 breakfast bar with labeled sections for cereal and fruit, a blue oatmeal container, and a variety of condiments and utensils.

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

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

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

Bedford Park

Roberto

฿4,646

฿5,458 total

includes taxes & fees

18 Nov - 19 Nov

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a staircase, and large windows providing natural light.

A Wingate by Wyndham hotel with a symmetrical facade, large windows, and a central entrance.

A hotel room with a bed, a desk, a chair, a sofa, and a television.

A modern restaurant with a mix of seating options including tables and sofas, a kitchen area, and large windows offering views of the outdoors.

3. Wingate by Wyndham Tinley Park

Tinley Park

Erica

฿4,176

฿4,718 total

includes taxes & fees

25 Oct - 26 Oct

A modern lobby with sofas, tables, and a reception desk.

A modern interior with a flat-screen TV displaying a menu, decorative golden star-shaped objects on mirrored stands, and a tiled floor.

A hotel with a flat facade, a parking lot, and a well-lit entrance.

A modern bar area with stools, a large TV, and a decorative plant.

4. Baymont by Wyndham Chicago/Alsip

Alsip

James

฿3,097

฿3,499 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

5. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

฿4,512

฿5,631 total

includes taxes & fees

1 Nov - 2 Nov

A modern spa with a circular hot tub, a sofa, and a view of the city.

A modern lobby with a central reception desk, seating areas, and decorative lighting.

A modern lounge area with a sofa, lounge chairs, and a pool table.

A spacious room with a large bed, a TV, a mirror, and a view of the city.

6. Wind Creek Chicago Southland Casino and Hotel

East Hazel Crest

Lloyd

฿5,986

฿6,704 total

includes taxes & fees

19 Oct - 20 Oct

A spacious lobby with a wooden floor, a staircase with a green accent, and a reception area with a sign reading "Welcome".

A Sleep Inn hotel with a prominent tower, a covered entrance, and a landscaped front yard.

A hotel reception area with a staircase, reception desk, and a large potted plant.

A modern living room with sofas, a coffee table, and a fireplace.

7. Sleep Inn Midway Airport Bedford Park

Bedford Park

Diane

฿3,043

฿3,575 total

includes taxes & fees

8 Nov - 9 Nov

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 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.

8. Jaslin Hotel

Chinatown

Jeffrey

฿4,971

฿5,910 total

includes taxes & fees

9 Nov - 10 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

9. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

฿5,085

฿6,046 total

includes taxes & fees

1 Nov - 2 Nov

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

A modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

A hotel room with a large bed, two bedside lamps, and a city view through a large window.

10. Hyatt Place Chicago/River North

Downtown Chicago

Nilofar

฿5,816

฿6,914 total

includes taxes & fees

12 Nov - 13 Nov

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

A bar area with a marble countertop, bar stools, and a variety of bottles.

11. Hotel Riu Plaza Chicago

Downtown Chicago

Scott E

฿6,187

฿8,308 total

includes taxes & fees

11 Nov - 12 Nov

A reception area with a modern design, featuring a reception desk, a digital display, and a wooden accent wall.

A modern hotel room with a large bed, a desk, and a chair.

12. Holiday Inn Express & Suites Chicago - Oak Forest by IHG

Oak Forest

Freyda

฿3,844

฿4,497 total

includes taxes & fees

8 Nov - 9 Nov

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

A modern lounge area with seating, a bar, and large windows offering views.

A modern gym with various exercise equipment, large windows, and a city view.

A view from a window with a cityscape in the background, including modern buildings and a clear sky.

13. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

฿6,518

฿7,749 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

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

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.

14. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

฿5,744

฿6,829 total

includes taxes & fees

3 Nov - 4 Nov

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

A residential street with a sidewalk, houses, and greenery.

15. Carleton of Oak Park

Oak Park

Brad

฿4,091

฿4,540 total

includes taxes & fees

27 Oct - 28 Oct

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A bar area with a long counter, blue bar stools, and a variety of bottles and glasses.

A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

A modern room with a view of a river and high-rise buildings.

16. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

James

฿7,415

฿9,810 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with a glass table, orange cushions, and potted plants.

A modern living room with a fireplace, large windows, and a flat-screen TV mounted on the wall.

A modern building with a large glass facade and a river in front.

A modern hotel lobby with a bar area, seating arrangements, and decorative lighting.

17. Sheraton Grand Chicago Riverwalk

Downtown Chicago

Stacie

฿7,320

฿9,895 total

includes taxes & fees

13 Nov - 14 Nov

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

18. Hilton Chicago

Downtown Chicago

Anna

฿5,654

฿7,703 total

includes taxes & fees

13 Nov - 14 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

A person sitting by a window with a cityscape view.

19. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Said Lopez

฿7,086

฿9,594 total

includes taxes & fees

31 Oct - 1 Nov

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.

A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.

20. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Richard

฿4,574

฿5,438 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Far Southeast Side attractions

Abbott Park

Abbott 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.

See properties

Harborside International Golf Center

Enjoy a round of golf in Chicago at Harborside International Golf Center. Stroll along the lakeside or attend a sporting event in this vibrant area.

See properties

Pullman Historic District

Find out about the history of Chicago when you take a trip to Pullman Historic District. Take in the museums while you're in the area.

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Jones Convocation Center

Catch an event at Jones Convocation Center during your trip to Chicago. Amble around the area's parks or visit its shops.

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Chicago State University

Explore the campus of Chicago State University as part of your travels around Chicago. Amble around the area's parks or visit its shops.

See properties

Johnson Products

Find out about the history of Chicago with a stop at Johnson Products. Amble around the area's beaches or visit its shops.

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Mahalia Jackson Residence

You can find out about the history of Chicago with a stop at Mahalia Jackson Residence. Experience the area's entertainment choices and live music.

See properties

A. Philip Randolph Pullman Porter Museum

You can spend time studying the exhibits at A. Philip Randolph Pullman Porter Museum in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

See properties

Learn more about Far Southeast Side

Discover things to see and do in Far Southeast Side as you venture to popular sights like Lake Michigan.

See all hotels in Far Southeast Side

A man standing on a rocky outcrop with a large concrete structure in the background.

Top Far Southeast Side Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"We had an early arrival, and first had only planned to store the luggage. Very friendly at reception had a nice surprise that rooms were already available - no extra costs. All staff was very attentive,"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Room is spacious, very clean hotel. I would recommend."

Freehand Chicago

10/10 Excellent

"It was comfortable"

More cheap stays in Far Southeast Side

Motel 6 Bridgeview, IL

9625 S 76th Ave Bridgeview IL

฿2,059

฿2,305 total

26 Oct - 27 Oct

includes taxes & fees

7.2/10 Good! (1,574 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,699

฿3,022 total

24 Oct - 25 Oct

includes taxes & fees

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

฿2,978

฿3,424 total

1 Nov - 2 Nov

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

฿3,043

฿3,575 total

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (2,171 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿3,665

฿4,357 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,681 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿3,743

฿4,451 total

11 Nov - 12 Nov

includes taxes & fees

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Book Hotels in Far Southeast Side on Expedia.com

Find hotels in Far Southeast Side, IL from ฿2,305

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Far Southeast Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Far Southeast Side hotels

1. Admiral Motel By Oyo Chicago I-94

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

3. Wingate by Wyndham Tinley Park

4. Baymont by Wyndham Chicago/Alsip

5. Holiday Inn Chicago – Midway Airport S by IHG

6. Wind Creek Chicago Southland Casino and Hotel

7. Sleep Inn Midway Airport Bedford Park

8. Jaslin Hotel

9. Embassy Suites by Hilton Chicago Downtown River North

10. Hyatt Place Chicago/River North

11. Hotel Riu Plaza Chicago

12. Holiday Inn Express & Suites Chicago - Oak Forest by IHG

13. Hyatt House Chicago/West Loop-Fulton Market

14. Hilton Vacation Club Hotel Blake Chicago

15. Carleton of Oak Park

16. LondonHouse Chicago, Curio Collection by Hilton

17. Sheraton Grand Chicago Riverwalk

18. Hilton Chicago

19. InterContinental Chicago Magnificent Mile by IHG

20. Courtyard by Marriott Chicago Magnificent Mile

Stay near popular Far Southeast Side attractions

Abbott Park

Harborside International Golf Center

Pullman Historic District

Jones Convocation Center

Chicago State University

Johnson Products

Mahalia Jackson Residence

A. Philip Randolph Pullman Porter Museum

Learn more about Far Southeast Side

Top Far Southeast Side Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

The Royal Sonesta Chicago Downtown

Freehand Chicago

More cheap stays in Far Southeast Side

Motel 6 Bridgeview, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Quality Inn O'Hare Airport

Sleep Inn Midway Airport Bedford Park

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Explore a world of travel with Expedia

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