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 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.

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.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Ashima

Rp2.355.118

Rp2.944.454 total

includes taxes & fees

27 Oct - 28 Oct

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

A reception area with a wooden reception desk, a sofa, and a coffee table.

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.

2. Carlton Inn Midway

Archer Heights

Icaro

Rp1.874.802

Rp2.200.961 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

3. Rainbow Motel

Garfield Ridge

Jerry

Rp1.377.636

Rp1.617.178 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

4. L7 Chicago by LOTTE

Downtown Chicago

Emily

Rp4.732.708

Rp5.626.718 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

Rp4.470.050

Rp5.314.656 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

6. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

Rp4.231.617

Rp5.541.205 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

7. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Lauren

Rp3.811.336

Rp4.531.297 total

includes taxes & fees

25 Oct - 26 Oct

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.

8. River Hotel

Downtown Chicago

Jared

Rp3.343.908

Rp3.975.571 total

includes taxes & fees

25 Oct - 26 Oct

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

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

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.

9. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

Rp2.516.920

Rp2.893.956 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A residential street with a sidewalk, houses, and greenery.

10. Carleton of Oak Park

Oak Park

Brad

Rp2.191.327

Rp2.431.935 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

11. Silversmith Hotel Chicago Downtown

Downtown Chicago

Abigail

Rp3.562.071

Rp4.783.636 total

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a grand staircase, a large abstract painting, and a seating area with modern furniture.

A hotel with a classic facade, multiple flags, and a prominent entrance.

A spacious hotel lobby with a bar area, dining tables, and a central seating area.

12. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Kurt

Rp3.415.820

Rp4.636.362 total

includes taxes & fees

25 Oct - 26 Oct

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

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

13. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Kelly

Rp3.150.928

Rp3.746.139 total

includes taxes & fees

27 Oct - 28 Oct

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.

The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

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

14. Swissotel - Chicago

Downtown Chicago

Michael

Rp4.202.357

Rp5.629.368 total

includes taxes & fees

30 Oct - 31 Oct

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.

15. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

Rp3.759.200

Rp4.469.312 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

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.

16. citizenM Chicago Downtown

Downtown Chicago

Kimberly

Rp3.703.468

Rp4.403.053 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. Hyatt Place Chicago/River North

Downtown Chicago

Iminique

Rp3.973.138

Rp4.723.666 total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

18. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Poua

Rp3.499.418

Rp4.160.457 total

includes taxes & fees

25 Oct - 26 Oct

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

A high-rise building with a modern architectural design, featuring a prominent glass facade and a series of vertical lines.

A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.

19. Arlo Chicago

Downtown Chicago

Ashley Nacole

Rp3.624.412

Rp4.873.752 total

includes taxes & fees

25 Oct - 26 Oct

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

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

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

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

20. Hyatt Centric The Loop Chicago

Downtown Chicago

Lavaniel

Rp4.836.082

Rp6.199.406 total

includes taxes & fees

29 Oct - 30 Oct

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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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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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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.

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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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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

L7 Chicago by LOTTE

10/10 Excellent

"The room was really fantastic, although it could have used a little more lighting. The staff was wonderful and the restaurant food was fantastic. The only caveat was if you pay for the breakfast, you have to eat it that day or lose the $50.I wasn’t crazy about that but other than that it was a great stay"

River Hotel

8/10 Good

"."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good

"The hotel is very well located, the only thing is that in the room there were extra support columns in a corner that didn't look very safe, maybe they are but that doesn't give the best impression."

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

Rp1.102.646

Rp1.267.822 total

5 Oct - 6 Oct

includes taxes & fees

6.8/10 (2,355 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

Rp1.324.822

Rp1.483.536 total

30 Sept - 1 Oct

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

Rp1.673.751

Rp1.857.530 total

30 Sept - 1 Oct

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

Rp2.516.920

Rp2.893.956 total

25 Oct - 26 Oct

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

Rp2.804.568

Rp3.334.351 total

25 Oct - 26 Oct

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

Rp3.759.200

Rp4.469.313 total

25 Oct - 26 Oct

includes taxes & fees

Explore a world of travel with Expedia

Book Hotels in Southwest Side on Expedia.com

Find hotels in Southwest Side, IL from Rp1.267.822

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. L7 Chicago by LOTTE

5. Hilton Vacation Club Hotel Blake Chicago

6. Hotel Riu Plaza Chicago

7. Hyatt Place Chicago/Downtown - The Loop

8. River Hotel

9. Hampton Inn Chicago-O'Hare International Airport

10. Carleton of Oak Park

11. Silversmith Hotel Chicago Downtown

12. The Allegro Royal Sonesta Hotel Chicago Loop

13. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

14. Swissotel - Chicago

15. Homewood Suites by Hilton Chicago Downtown South Loop

16. citizenM Chicago Downtown

17. Hyatt Place Chicago/River North

18. DoubleTree by Hilton Chicago - Magnificent Mile

19. Arlo Chicago

20. Hyatt Centric The Loop Chicago

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

Union Stock Yard Gate

S.S. Peter and Paul Church

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

L7 Chicago by LOTTE

River Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia

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