Far Southeast Side Holiday Rentals, Chicago: Private House Rentals

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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 bathroom with a toilet, sink, and bathtub.

A brick building with a sign for the Admiral Motel.

1. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

฿2,757

฿3,236 total

includes taxes & fees

1 Nov - 2 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 hotel room with a bed, a desk, a chair, a sofa, and a television.

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

A swimming pool with lounge chairs and a view of the outside.

2. Wingate by Wyndham Tinley Park

Tinley Park

Erica

฿4,216

฿4,763 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a large window, a dining area, and a view of the sea.

A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

A modern restaurant interior with a long counter, booths, and tables.

3. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

฿4,814

฿5,724 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

4. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Shanequa

฿6,353

฿8,708 total

includes taxes & fees

12 Nov - 13 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-level indoor area with a central water feature, surrounded by seating areas and greenery.

5. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

฿5,099

฿6,063 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

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

6. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

฿6,535

฿7,770 total

includes taxes & fees

1 Nov - 2 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 modern interior with a long counter, glass partitions, and a brick wall backdrop.

7. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

฿6,535

฿7,770 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

8. Hilton Chicago

Downtown Chicago

Anna

฿5,567

฿7,615 total

includes taxes & fees

30 Oct - 31 Oct

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

9. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

฿4,245

฿5,046 total

includes taxes & fees

9 Nov - 10 Nov

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

A person sitting by a window with a cityscape view.

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.

10. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

฿7,131

฿9,655 total

includes taxes & fees

31 Oct - 1 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

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

A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.

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

11. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

฿5,674

฿6,746 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A spacious lobby with a marble floor, a reception desk, and a glass partition.

12. Hotel Riu Plaza Chicago

Downtown Chicago

Suki

฿5,560

฿7,569 total

includes taxes & fees

10 Nov - 11 Nov

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

A modern hotel with a corner location, large windows, and a green awning.

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

13. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

฿4,480

฿5,326 total

includes taxes & fees

1 Nov - 2 Nov

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

A cityscape with modern high-rise buildings, a river, and a boat.

14. Hyatt Regency Chicago

Downtown Chicago

Addison

฿8,005

฿10,717 total

includes taxes & fees

31 Oct - 1 Nov

A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.

A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.

A large banquet hall with round tables, blue tablecloths, and white chairs with blue sashes.

A conference room with a long table, chairs, a projector screen, and a carpeted floor.

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

฿4,928

฿6,843 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A vending machine with various beverages and snacks.

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

16. Hyatt Place Chicago/River North

Downtown Chicago

Nilofar

฿5,852

฿6,958 total

includes taxes & fees

12 Nov - 13 Nov

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

A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

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.

17. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

฿5,780

฿6,872 total

includes taxes & fees

3 Nov - 4 Nov

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

A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

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

18. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Jeanmarie

฿4,587

฿5,453 total

includes taxes & fees

1 Nov - 2 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 residential street with a sidewalk, houses, and greenery.

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

19. Carleton of Oak Park

Oak Park

Brad

฿4,102

฿4,553 total

includes taxes & fees

21 Oct - 22 Oct

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

20. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Vincenzo

฿5,384

฿6,401 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.

See properties

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.

See properties

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.

See properties

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 Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."

The Wade

10/10 Excellent

"Loved this trendy hotel. Great location, amenities, and service."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great central Chicago location; everything was walkable from this great hotel."

The Godfrey Hotel Chicago

10/10 Excellent

"Godfrey is a beautiful hotel in a great location. I had the deluxe King room that was very spacious and it had an amazing view. Staff was friendly and attentive. I will definitely be staying here when I am back in Chicago."

Fairmont Chicago at Millennium Park

10/10 Excellent

"clean, perfect for a family trip!"

Hilton Chicago

10/10 Excellent

"The property was great"

Freehand Chicago

10/10 Excellent

"It was comfortable"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"The staff was 10/10."

Hyatt Regency Chicago

10/10 Excellent

"Great location"

More cheap stays in Far Southeast Side

Motel 6 Bridgeview, IL

9625 S 76th Ave Bridgeview IL

฿2,064

฿2,311 total

29 Oct - 30 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,706

฿3,030 total

23 Oct - 24 Oct

includes taxes & fees

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

฿2,986

฿3,434 total

1 Nov - 2 Nov

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

฿3,051

฿3,584 total

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (2,164 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿3,675

฿4,369 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,671 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿3,902

฿4,639 total

10 Nov - 11 Nov

includes taxes & fees

7.8/10 Good! (2,909 reviews)

Explore a world of travel with Expedia

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Book Hotels in Far Southeast Side on Expedia.com

Find hotels in Far Southeast Side, IL from ฿2,311

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. Wingate by Wyndham Tinley Park

3. Homewood Suites by Hilton Chicago Downtown South Loop

4. Sable at Navy Pier Chicago, Curio Collection by Hilton

5. Embassy Suites by Hilton Chicago Downtown River North

6. Hyatt Place Chicago/Downtown - The Loop

7. Hyatt House Chicago/West Loop-Fulton Market

8. Hilton Chicago

9. Hilton Garden Inn Chicago Downtown South Loop

10. InterContinental Chicago Magnificent Mile by IHG

11. L7 Chicago by LOTTE

12. Hotel Riu Plaza Chicago

13. Hampton Inn & Suites Chicago Downtown

14. Hyatt Regency Chicago

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

16. Hyatt Place Chicago/River North

17. Hilton Vacation Club Hotel Blake Chicago

18. Courtyard by Marriott Chicago Magnificent Mile

19. Carleton of Oak Park

20. Hilton Chicago/Magnificent Mile Suites

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 Chicago Hotel Collection Ambassador Gold Coast

The Wade

The Chicago Hotel Collection - Magnificent Mile

The Godfrey Hotel Chicago

Fairmont Chicago at Millennium Park

Hilton Chicago

Freehand Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Hyatt Regency 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

Go further with the Expedia app