Far Southwest Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for Far Southwest Side hotels

A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.

A room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.

A modern hotel room with a large bed, a nightstand, a wall-mounted lamp, and a door.

1. Motel 6 - Chicago, IL

Washington Heights

DENNIS

฿3,038

฿3,567 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

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

Ashburn

Pedro

฿2,902

฿3,697 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

3. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

฿3,702

฿4,402 total

includes taxes & fees

23 Nov - 24 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 modern gym with various exercise equipment, large windows, and a city view.

4. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

฿4,558

฿5,419 total

includes taxes & fees

23 Nov - 24 Nov

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

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.

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

5. Carleton of Oak Park

Oak Park

Brad

฿4,130

฿4,584 total

includes taxes & fees

27 Oct - 28 Oct

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

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

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

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

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

Downtown Chicago

Angela

฿4,420

฿6,419 total

includes taxes & fees

23 Nov - 24 Nov

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.

A snack and beverage kiosk with various snacks and drinks.

7. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Shonnette

฿3,011

฿3,342 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

8. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

฿4,276

฿5,084 total

includes taxes & fees

22 Nov - 23 Nov

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

9. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

฿3,272

฿3,890 total

includes taxes & fees

23 Nov - 24 Nov

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

A grand ballroom with ornate chandeliers, a multi-tiered wedding cake centerpiece, and elegant floral arrangements on tables.

A spacious lobby with a grand piano, comfortable seating areas, and a fireplace.

A hotel lobby with seating areas, a fireplace, and a staircase.

10. Hilton Chicago

Downtown Chicago

Anna

฿4,563

฿6,416 total

includes taxes & fees

22 Nov - 23 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.

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

11. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Richard

฿3,719

฿4,422 total

includes taxes & fees

23 Nov - 24 Nov

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

A vending machine with various beverages and snacks.

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

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

12. Hyatt Place Chicago/River North

Downtown Chicago

Nilofar

฿4,153

฿4,937 total

includes taxes & fees

22 Nov - 23 Nov

A modern interior with a bar area, seating, and decorative wooden panels.

A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

13. Best Western Grant Park Hotel

Downtown Chicago

Colin

฿3,313

฿3,938 total

includes taxes & fees

23 Nov - 24 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 swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

A person sitting by a window with a cityscape view.

14. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Said Lopez

฿6,179

฿8,528 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 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.

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

15. Hotel Riu Plaza Chicago

Downtown Chicago

Scott E

฿4,040

฿5,766 total

includes taxes & fees

23 Nov - 24 Nov

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

A modern hotel room with a large bed, a desk, a chair, a lamp, and a view of the city through large windows.

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

16. Le Méridien Essex Chicago

Downtown Chicago

Caitlin Vania

฿3,782

฿5,098 total

includes taxes & fees

23 Nov - 24 Nov

A cozy room with a sofa, a dining table, and a window with a view of buildings.

A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

17. LIVN - West Loop Chicago

Downtown Chicago

Tracy

฿4,406

฿5,172 total

includes taxes & fees

25 Oct - 26 Oct

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

A multi-level hotel lobby with a central food service area, multiple dining tables, and a modern architectural design.

A hotel room with a sectional sofa, a small dining table, a desk, and a bathroom visible through an open door.

18. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Patricia

฿3,989

฿5,734 total

includes taxes & fees

24 Nov - 25 Nov

A rooftop pool with lounge chairs and potted plants, surrounded by modern buildings.

A modern building with large glass windows and a covered walkway.

A modern lobby with a central seating area, a reception desk, and elevators.

A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.

19. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Donna

฿3,208

฿4,219 total

includes taxes & fees

23 Nov - 24 Nov

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

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

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

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

20. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Tracy

฿3,572

฿4,246 total

includes taxes & fees

24 Nov - 25 Nov

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Stay near popular Far Southwest Side attractions

Beverly Arts Center

Beverly Arts Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.

See properties

Carter G. Woodson Library

You can enjoy some culture when you stop by Carter G. Woodson Library in Chicago. Make some time to visit the shops while you're in the area.

See properties

Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.

See properties

Final Call Newspaper Headquarters

Find out about the history of Chicago when you take a trip to Final Call Newspaper Headquarters.

See properties

Top Far Southwest Side Hotel Reviews

Congress Plaza Hotel

8/10 Good

"The hotel itself is huge with the historic main room being spectacular. Our room was a hike to get to but very clean, newer vinyl flooring, newer paint. We needed a one night stay for an event further south in the city so it was perfect for that. The location is pretty wonderful with Buckingham fountain and the park right outside the front door. What wasn't so great was the front desk personnel. Seemed like they just hated their job. Not quite rude but getting there with my polite simple questions. Also the main restaurant was supposed to be open on Friday night but closed early? The bar area was unappealing so we ended up walking a block to the Conrad Hilton and had a great experience in their bar with food being served until late. Would we stay again? If for a short stay, yes."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"n/a"

Hilton Chicago

10/10 Excellent

"Staff was friendly and helpful."

Arlo Chicago

10/10 Excellent

"Very nice hotel."

More cheap stays in Far Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,725

฿3,051 total

2 Nov - 3 Nov

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

฿3,011

฿3,342 total

25 Oct - 26 Oct

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

฿3,074

฿3,611 total

15 Nov - 16 Nov

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿3,989

฿4,743 total

22 Nov - 23 Nov

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

฿4,221

฿4,853 total

1 Nov - 2 Nov

includes taxes & fees

9.4/10 Exceptional! (2,409 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿4,353

฿5,176 total

9 Nov - 10 Nov

includes taxes & fees

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Find hotels in Far Southwest Side, IL from ฿3,051

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Far Southwest Side

Check prices for these dates

Filter by

Star rating

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Our top choices for Far Southwest Side hotels

1. Motel 6 - Chicago, IL

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

3. Homewood Suites by Hilton Chicago Downtown South Loop

4. Hyatt House Chicago/West Loop-Fulton Market

5. Carleton of Oak Park

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

7. SureStay Plus Hotel by Best Western Chicago Lombard

8. Embassy Suites by Hilton Chicago Downtown River North

9. Hilton Garden Inn Chicago Downtown South Loop

10. Hilton Chicago

11. Courtyard by Marriott Chicago Magnificent Mile

12. Hyatt Place Chicago/River North

13. Best Western Grant Park Hotel

14. InterContinental Chicago Magnificent Mile by IHG

15. Hotel Riu Plaza Chicago

16. Le Méridien Essex Chicago

17. LIVN - West Loop Chicago

18. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

19. Holiday Inn & Suites Chicago - Downtown by IHG

20. Hampton Inn & Suites Chicago Downtown

Stay near popular Far Southwest Side attractions

Beverly Arts Center

Carter G. Woodson Library

Highland Community Bank

Final Call Newspaper Headquarters

Top Far Southwest Side Hotel Reviews

Congress Plaza Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago

Arlo Chicago

More cheap stays in Far Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

SureStay Plus Hotel by Best Western Chicago Lombard

Sleep Inn Midway Airport Bedford Park

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Explore a world of travel with Expedia

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