Far Southeast Side Holiday Rentals, Chicago: Private House Rentals

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 Far Southeast Side

Pet friendly

Apart hotel

Pool

Hot tub

Spa

Family friendly

Waterpark

Apartment

Cottage

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

A brick building with a sign for the Admiral Motel.

1. Admiral Motel By Oyo Chicago I-94

Chatham

Arlex

Rp1.479.842

Rp1.737.188 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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.

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

Downtown Chicago

Shanequa

Rp2.542.904

Rp3.644.658 total

includes taxes & fees

22 Nov - 23 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.

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

A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.

3. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

Rp2.512.267

Rp2.986.833 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

4. Carleton of Oak Park

Oak Park

Brad

Rp2.202.221

Rp2.444.033 total

includes taxes & fees

27 Oct - 28 Oct

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

A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.

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

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Sotina

Rp2.888.927

Rp3.434.453 total

includes taxes & fees

15 Nov - 16 Nov

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

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

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.

6. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

Rp2.205.893

Rp2.622.585 total

includes taxes & fees

11 Nov - 12 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 modern living room with a fireplace, a large sofa, a coffee table, and a bookshelf.

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

7. Hilton Chicago

Downtown Chicago

Anna

Rp2.435.673

Rp3.424.717 total

includes taxes & fees

22 Nov - 23 Nov

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

A modern interior with a long counter, glass partitions, and a brick wall backdrop.

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

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

8. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

Rp2.595.168

Rp3.085.393 total

includes taxes & fees

22 Nov - 23 Nov

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

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

9. Hotel Riu Plaza Chicago

Downtown Chicago

Scott E

Rp2.011.741

Rp2.905.387 total

includes taxes & fees

22 Nov - 23 Nov

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

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

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

A person sitting by a window with a cityscape view.

10. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Said Lopez

Rp3.298.026

Rp4.551.794 total

includes taxes & fees

22 Nov - 23 Nov

A room with two chairs and a small table, a large window with a city view at night.

A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.

A modern hotel lobby with a large window, seating area, and a reception desk.

A bar area with a long counter, multiple stools, and a television screen.

11. Eurostars Magnificent Mile

Downtown Chicago

Kelby

Rp2.335.651

Rp2.776.858 total

includes taxes & fees

22 Nov - 23 Nov

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

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

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

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

12. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

James

Rp2.588.860

Rp3.613.867 total

includes taxes & fees

22 Nov - 23 Nov

An outdoor seating area with modern furniture and potted plants.

A modern skyscraper with a unique wavy facade, surrounded by other high-rise buildings.

A corridor with a brick wall, hanging wicker light fixture, and potted plants.

A modern hotel with a rooftop pool, surrounded by high-rise buildings and a clear view of the city skyline.

13. Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Shannon

Rp2.838.825

Rp3.932.139 total

includes taxes & fees

22 Nov - 23 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

14. Hotel 505 River North

Downtown Chicago

Jordan

Rp2.865.498

Rp3.983.695 total

includes taxes & fees

22 Nov - 23 Nov

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

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

A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

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

15. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

Rp2.470.456

Rp2.937.126 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

16. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

Rp4.307.258

Rp5.763.976 total

includes taxes & fees

22 Nov - 23 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 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.

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

17. L7 Chicago by LOTTE

Downtown Chicago

Amanda

Rp2.613.010

Rp3.106.607 total

includes taxes & fees

22 Nov - 23 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 vending machine with various beverages and snacks.

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

18. Hyatt Place Chicago/River North

Downtown Chicago

Nilofar

Rp2.216.706

Rp2.635.441 total

includes taxes & fees

22 Nov - 23 Nov

A dining area with tables set for four, large windows with a view of city buildings, and a curved ceiling structure.

A spacious lobby with a patterned carpet, wooden paneling, and modern lighting fixtures.

A hotel room with a large bed, a desk with a lamp, a bench, and a view of the cityscape through large windows.

19. Omni Chicago Hotel

Downtown Chicago

Megan

Rp4.307.438

Rp5.721.066 total

includes taxes & fees

11 Nov - 12 Nov

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A hotel room with two beds, a desk, a chair, a large window with a view, and a modern wall design.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

20. The Wade

Downtown Chicago

Ashaleigh

Rp2.288.794

Rp2.721.147 total

includes taxes & fees

22 Nov - 23 Nov

View all properties

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

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

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

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

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

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

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

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

10/10 Excellent

"Friendly staff hotel well kept"

Congress Plaza Hotel

8/10 Good

"The staff is amazing, very knowledgeable and helpful. The only downside of my stay is the bed. It is super firm! No pillow top here."

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"perfect place to walk around and enjoy chicago , specially the numerous food outlets in close vicinity"

River Hotel

8/10 Good

"Great location and friendly staff!"

Sports Illustrated Resorts Chicago

10/10 Excellent

"Really nice rebrand of the v Virgin"

Fairmont Chicago at Millennium Park

10/10 Excellent

"I had a wonderful experience at The Fairmont in Chicago! The only thing I noticed were some bugs in the bathroom and a fly in the room, but the service supersedes these things. Thanks everyone!"

The Chicago Hotel Collection River North

10/10 Excellent

"For just a room it’s not bad"

More cheap stays in Far Southeast Side

Motel 6 Bridgeview, IL

9625 S 76th Ave Bridgeview IL

Rp1.108.127

Rp1.240.880 total

26 Oct - 27 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

Rp1.452.701

Rp1.626.735 total

30 Oct - 31 Oct

includes taxes & fees

6.4/10 (1,317 reviews)

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

Rp1.516.551

Rp1.743.731 total

22 Nov - 23 Nov

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

Rp1.640.632

Rp1.927.415 total

12 Nov - 13 Nov

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Rp2.162.640

Rp2.571.162 total

12 Nov - 13 Nov

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

Rp2.282.486

Rp2.713.647 total

22 Nov - 23 Nov

includes taxes & fees

Explore a world of travel with Expedia

Book Hotels in Far Southeast Side on Expedia.com

Find hotels in Far Southeast Side, IL from Rp1.240.880

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. Sable at Navy Pier Chicago, Curio Collection by Hilton

3. Homewood Suites by Hilton Chicago Downtown South Loop

4. Carleton of Oak Park

5. Hilton Vacation Club Hotel Blake Chicago

6. Hilton Garden Inn Chicago Downtown South Loop

7. Hilton Chicago

8. Hyatt House Chicago/West Loop-Fulton Market

9. Hotel Riu Plaza Chicago

10. InterContinental Chicago Magnificent Mile by IHG

11. Eurostars Magnificent Mile

12. LondonHouse Chicago, Curio Collection by Hilton

13. Radisson Blu Aqua Hotel Chicago

14. Hotel 505 River North

15. Embassy Suites by Hilton Chicago Downtown River North

16. Fairmont Chicago at Millennium Park

17. L7 Chicago by LOTTE

18. Hyatt Place Chicago/River North

19. Omni Chicago Hotel

20. The Wade

Stay near popular Far Southeast Side attractions

Abbott Park

Harborside International Golf Center

Pullman Historic District

Chicago State University

Jones Convocation Center

Johnson Products

A. Philip Randolph Pullman Porter Museum

Mahalia Jackson Residence

Learn more about Far Southeast Side

Top Far Southeast Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Congress Plaza Hotel

LondonHouse Chicago, Curio Collection by Hilton

River Hotel

Sports Illustrated Resorts Chicago

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection River North

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

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia

Go further with the Expedia app