Southwest Side Holiday Rentals, Chicago: Private House Rentals

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Go beyond your typical stay in Southwest Side

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

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.

A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Diane

2.975.628 ₫

3.754.110 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

Rahul Pandit

2.731.412 ₫

3.206.405 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

A reception desk with a glass partition, a no pets allowed sign, a no smoking sign, a QR code for check-in, and a sign indicating a 1-minute wait for guests.

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

3. Rainbow Motel

Garfield Ridge

Noel

2.007.087 ₫

2.356.078 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A hotel entrance with a marquee and string lights above the entrance.

A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.

A hotel entrance with a marquee, American flag, and a person standing in front.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

4.732.500 ₫

5.626.470 ₫ total

includes taxes & fees

2 Sept - 3 Sept

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.

5. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

LISA

4.408.027 ₫

5.240.704 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

6. Hotel Riu Plaza Chicago

Downtown Chicago

Peter

4.683.015 ₫

6.311.544 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

A modern lobby with a seating area, a bar, and a green wall.

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

7. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

MAGALY

4.055.385 ₫

4.821.449 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

Downtown Chicago

Ashraf

4.461.876 ₫

6.204.722 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

A man in a suit sitting by a window with a vase of red flowers.

9. River Hotel

Downtown Chicago

Patti

3.398.876 ₫

4.040.779 ₫ total

includes taxes & fees

8 Sept - 9 Sept

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A grilled pineapple on top of a stack of meat, served on a pan.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

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

10. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

4.360.295 ₫

5.836.071 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A modern building with a colorful facade and a red circular seating area.

A modern high-rise building with a glass facade, surrounded by other tall buildings.

A modern interior with wooden shelves, colorful chairs, and hanging plants.

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

11. citizenM Chicago Downtown

Downtown Chicago

lakadria

4.437.340 ₫

5.275.554 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

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.

12. L7 Chicago by LOTTE

Downtown Chicago

Girivasan

5.614.540 ₫

6.675.126 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

13. The Royal Sonesta Chicago River North

Downtown Chicago

Jennifer Lynn

5.190.517 ₫

7.006.024 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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 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.

14. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Hugo

3.968.528 ₫

4.718.183 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

15. Hyatt Place Chicago/River North

Downtown Chicago

Shoma

4.434.110 ₫

5.271.713 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

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

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

16. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

susie

4.190.234 ₫

4.981.770 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A spacious lobby with a central coffee table, sofas, and a large mirror.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

17. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Alma

3.729.087 ₫

4.433.512 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A tall, modern hotel with a brick facade and numerous windows.

A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.

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

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Belle

4.089.814 ₫

4.862.381 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

19. Hyatt Regency Chicago

Downtown Chicago

Abdulsamad

5.946.036 ₫

8.000.299 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

A cityscape with modern skyscrapers, a waterfront, and a winter setting.

20. Silversmith Hotel Chicago Downtown

Downtown Chicago

Xiao

3.773.957 ₫

5.283.492 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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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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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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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 acclaimed theatre scene.

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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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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.

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 Wade

10/10 Excellent

"The room was beautiful and the scenery outside of my window was beautiful"

Hotel Riu Plaza Chicago

10/10 Excellent

"Everything was Great"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Clean and accessible"

Fairmont Chicago at Millennium Park

10/10 Excellent

"They were so accommodating. I thoroughly enjoyed the stay."

L7 Chicago by LOTTE

10/10 Excellent

"clean and new"

River Hotel

10/10 Excellent

"Convenient location near the CTA redline"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"😁"

More cheap stays in Southwest Side

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

1.491.687 ₫

1.662.931 ₫ total

13 Sept - 14 Sept

includes taxes & fees

7.8/10 Good! (1,466 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

1.640.621 ₫

1.837.167 ₫ total

10 Sept - 11 Sept

includes taxes & fees

6.4/10 (1,250 reviews)

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

2.192.798 ₫

2.455.495 ₫ total

20 Sept - 21 Sept

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

3.051.711 ₫

3.628.406 ₫ total

30 Aug - 31 Aug

includes taxes & fees

7.6/10 Good! (2,795 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

2.975.628 ₫

3.754.110 ₫ total

8 Sept - 9 Sept

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

3.968.528 ₫

4.718.182 ₫ total

31 Aug - 1 Sept

includes taxes & fees

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Book Hotels in Southwest Side on Expedia.com

Find hotels in Southwest Side, IL from 1.662.931 ₫

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. Hyatt Place Chicago/Downtown - The Loop

6. Hotel Riu Plaza Chicago

7. DoubleTree by Hilton Chicago - Magnificent Mile

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

9. River Hotel

10. Hyatt Centric The Loop Chicago

11. citizenM Chicago Downtown

12. L7 Chicago by LOTTE

13. The Royal Sonesta Chicago River North

14. Embassy Suites by Hilton Chicago Downtown River North

15. Hyatt Place Chicago/River North

16. Hilton Chicago/Magnificent Mile Suites

17. The Chicago Hotel Collection Ambassador Gold Coast

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

19. Hyatt Regency Chicago

20. Silversmith Hotel Chicago Downtown

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

S.S. Peter and Paul Church

Union Stock Yard Gate

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Wade

Hotel Riu Plaza Chicago

Club Quarters Hotel, Central Loop, Chicago

Fairmont Chicago at Millennium Park

L7 Chicago by LOTTE

River Hotel

The Chicago Hotel Collection Ambassador Gold Coast

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Quality Inn & Suites Orland Park - Chicago

Travelodge by Wyndham Downtown Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia

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