Southwest Side Holiday Rentals, Chicago: Private House Rentals

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Our top choices for Southwest Side hotels

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

A modern lobby with a vending machine, a statue, and an exit sign.

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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

3.500.820 ₫

4.368.932 ₫ total

includes taxes & fees

13 Nov - 14 Nov

A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.

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

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.

2. Carlton Inn Midway

Archer Heights

stephen T

3.085.908 ₫

3.622.763 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A modern hotel room with a large bed, a flat-screen TV mounted on the ceiling, and a nightstand with a lamp.

A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

A compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

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

3. Rainbow Motel

Garfield Ridge

Jerry

1.811.674 ₫

2.126.725 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

4.456.155 ₫

5.298.167 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

5. Hotel 505 River North

Downtown Chicago

Giana

4.901.148 ₫

6.657.143 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

A reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

6. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

3.234.000 ₫

3.718.453 ₫ total

includes taxes & fees

1 Nov - 2 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 modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

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

7. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Keeven

5.951.394 ₫

7.846.831 ₫ total

includes taxes & fees

1 Nov - 2 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.

8. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

5.497.584 ₫

7.443.699 ₫ 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 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.

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

9. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

5.029.517 ₫

5.979.593 ₫ 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 marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A conference room with a long table, chairs, and a large screen.

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

10. Hilton Chicago

Downtown Chicago

Anna

4.298.748 ₫

5.871.885 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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.

11. Hotel Riu Plaza Chicago

Downtown Chicago

Kevin

4.543.467 ₫

6.139.079 ₫ total

includes taxes & fees

11 Nov - 12 Nov

An outdoor seating area with modern furniture and potted plants.

A modern interior with a staircase, glass railings, and a visible restaurant area.

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

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

12. Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Shannon

6.124.420 ₫

8.081.028 ₫ total

includes taxes & fees

31 Oct - 1 Nov

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

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

A gym with cardio machines, weight benches, and a large window offering a city view.

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

13. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

5.056.740 ₫

6.011.960 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

A modern interior with a central fireplace, seating area, and wall-mounted lighting.

A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

14. The Royal Sonesta Chicago Downtown

Downtown Chicago

5.419.788 ₫

7.273.409 ₫ total

includes taxes & fees

11 Nov - 12 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.

15. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

4.386.398 ₫

5.214.989 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

16. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

5.056.740 ₫

6.011.960 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

Downtown Chicago

Shanequa

5.312.170 ₫

7.209.775 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A dining table set for six with a cityscape view through large windows.

A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.

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

A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

18. Swissotel - Chicago

Downtown Chicago

Hilary

6.884.946 ₫

9.098.838 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

A modern bar area with a bar counter, multiple stools, and a chandelier.

A modern living room with a dark sofa set, a glass coffee table, and a decorative chandelier.

A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

19. Silversmith Hotel Chicago Downtown

Downtown Chicago

Guy

3.749.378 ₫

5.249.080 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

A modern bar area with a circular seating arrangement, a staircase leading to an upper level, and a view of the city through large windows.

20. Eurostars Magnificent Mile

Downtown Chicago

Will

3.734.208 ₫

4.439.600 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

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Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate.

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Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

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Ephraim Bajar Cultural Center

Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.

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S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

See properties

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

An airport with multiple runways, parked airplanes, and a large terminal building.

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great location, beautiful lobby area, quiet clean rooms."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Had an amazing stay"

Hotel Saint Clair- Magnificent Mile

8/10 Good

"Great stay"

Fairmont Chicago at Millennium Park

10/10 Excellent

"A staff member was kind enough to let us know about a parking lot near by that saved us money. We ate dinner at Toro. Steaks cooked to perfection! Food and atmosphere was fantastic!"

The Wade

10/10 Excellent

"Great location for those that want to be downtown with easy access to everything!"

The Godfrey Hotel Chicago

8/10 Good

"The hotel was nice, and the location was great. However, the property could use a little updating and more attention to detail, especially with the bathroom amenities. The hallways were also quite noisy, with a lot of partying going on. I certainly don’t mind people having a good time, but it did get a bit loud. Overall, it was an okay stay, but I felt it was overpriced for what was offered. There were other hotels nearby at about the same price that appeared to be substantially nicer. Not a bad experience, just not quite worth the price."

River Hotel

10/10 Excellent

"I absolutely loved this place. Close to everything and great view"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great location... Amazing hotel..."

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

1.593.456 ₫

1.832.154 ₫ total

22 Oct - 23 Oct

includes taxes & fees

6.8/10 (2,349 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

2.088.944 ₫

2.339.200 ₫ total

21 Oct - 22 Oct

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

2.509.958 ₫

2.785.551 ₫ total

21 Oct - 22 Oct

includes taxes & fees

9/10 Wonderful! (3,049 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

2.843.444 ₫

3.380.571 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

2.987.366 ₫

3.551.679 ₫ total

12 Nov - 13 Nov

includes taxes & fees

7.8/10 Good! (2,909 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

3.234.000 ₫

3.718.453 ₫ total

1 Nov - 2 Nov

includes taxes & fees

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Book Hotels in Southwest Side on Expedia.com

Find hotels in Southwest Side, IL from 1.832.154 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Southwest Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Southwest Side hotels

1. Holiday Inn Chicago – Midway Airport S by IHG

2. Carlton Inn Midway

3. Rainbow Motel

4. Hilton Vacation Club Hotel Blake Chicago

5. Hotel 505 River North

6. Hampton Inn Chicago-O'Hare International Airport

7. LondonHouse Chicago, Curio Collection by Hilton

8. InterContinental Chicago Magnificent Mile by IHG

9. L7 Chicago by LOTTE

10. Hilton Chicago

11. Hotel Riu Plaza Chicago

12. Radisson Blu Aqua Hotel Chicago

13. Hyatt Place Chicago/Downtown - The Loop

14. The Royal Sonesta Chicago Downtown

15. Embassy Suites by Hilton Chicago Downtown River North

16. Hyatt House Chicago/West Loop-Fulton Market

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

18. Swissotel - Chicago

19. Silversmith Hotel Chicago Downtown

20. Eurostars Magnificent Mile

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

S.S. Peter and Paul Church

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection - Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Fairmont Chicago at Millennium Park

The Wade

The Godfrey Hotel Chicago

River Hotel

The Royal Sonesta Chicago Downtown

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

Red Roof Inn PLUS+ Chicago - Willowbrook

SureStay Plus Hotel by Best Western Chicago Lombard

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago-O'Hare International Airport

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