Southwest 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 Southwest Side

Pet friendly

Apart hotel

Pool

Spa

Hot tub

Family friendly

Apartment

Condo

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

Paulina

฿4,532

฿5,655 total

includes taxes & fees

3 Nov - 4 Nov

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

stephen T

฿3,595

฿4,220 total

includes taxes & fees

20 Oct - 21 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 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

฿2,820

฿3,310 total

includes taxes & fees

16 Oct - 17 Oct

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

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

A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

฿5,768

฿6,858 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

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.

5. Hotel 505 River North

Downtown Chicago

Giana

฿6,021

฿8,235 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

6. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

฿6,559

฿7,798 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.

7. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

฿6,559

฿7,798 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 restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

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.

8. Hilton Chicago

Downtown Chicago

Anna

฿5,564

฿7,600 total

includes taxes & fees

30 Oct - 31 Oct

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 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.

9. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

฿5,118

฿6,084 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a large window with curtains.

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.

10. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

฿4,496

฿5,345 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. Hotel Riu Plaza Chicago

Downtown Chicago

Kevin

฿5,895

฿7,965 total

includes taxes & fees

11 Nov - 12 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 person sitting by a window with a cityscape view.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

12. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

฿7,116

฿9,635 total

includes taxes & fees

31 Oct - 1 Nov

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

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

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.

13. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Corinn

฿4,822

฿5,733 total

includes taxes & fees

10 Nov - 11 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 corridor with a brick wall, hanging wicker light fixture, and potted plants.

14. Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Shannon

฿7,962

฿10,506 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 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.

A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.

15. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

฿6,457

฿7,677 total

includes taxes & fees

1 Nov - 2 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 modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.

16. Hyatt Place Chicago/River North

Downtown Chicago

Iminique

฿5,841

฿6,944 total

includes taxes & fees

12 Nov - 13 Nov

A hotel lobby with a bar area, a chandelier, and a reception desk.

A view through a circular window of a cityscape with modern buildings and a body of water in the distance.

A lobby with a sofa, a coffee table, and an ottoman. There are wooden columns and a chandelier.

A hotel lobby with leather seating, a flat-screen TV, and large windows with a view of the cityscape.

17. Residence Inn Chicago Downtown/Loop

Downtown Chicago

Karla

฿8,023

฿9,538 total

includes taxes & fees

13 Nov - 14 Nov

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

A restaurant with multiple tables and chairs, a kitchen area, and a large screen on the wall.

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

A modern office space with a desk, chairs, and a printer.

18. Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

Cindy

฿5,213

฿6,198 total

includes taxes & fees

1 Nov - 2 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 lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

19. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

฿4,251

฿5,054 total

includes taxes & fees

11 Nov - 12 Nov

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

A large banquet hall with round tables, blue tablecloths, and white chairs with blue sashes.

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

A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

฿5,146

฿7,105 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Hotels recommended for families in Southwest Side

Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

฿4,532

฿5,655 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

Hampton Inn Chicago-O'Hare International Airport

Schiller Park

฿4,204

฿4,834 total

includes taxes & fees

1 Nov - 2 Nov

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

฿6,559

฿7,798 total

includes taxes & fees

1 Nov - 2 Nov

Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

฿6,559

฿7,798 total

includes taxes & fees

1 Nov - 2 Nov

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

฿5,118

฿6,084 total

includes taxes & fees

1 Nov - 2 Nov

Hilton Chicago

Downtown Chicago

฿5,564

฿7,600 total

includes taxes & fees

30 Oct - 31 Oct

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

฿5,768

฿6,858 total

includes taxes & fees

4 Nov - 5 Nov

Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

฿4,822

฿5,733 total

includes taxes & fees

10 Nov - 11 Nov

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

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.

See properties

Union Stock Yard Gate

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

See properties

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.

See properties

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

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 Royal Sonesta Chicago Downtown

8/10 Good

"Room was good … but there was really bad sewer smell in bathroom"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Had a great stay and the staff was fantastic"

Hilton Chicago O'Hare Airport

10/10 Excellent

"The convenience of the hotel location is key. But for what they charging PLEASE UPDATE THE HOTEL and not just the entrance."

Hyatt Regency Chicago

10/10 Excellent

"Great location"

The Godfrey Hotel Chicago

10/10 Excellent

"Amazing locations and staff!"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

฿2,067

฿2,377 total

21 Oct - 22 Oct

includes taxes & fees

6.8/10 (2,350 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

฿2,710

฿3,035 total

21 Oct - 22 Oct

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

฿3,249

฿3,606 total

21 Oct - 22 Oct

includes taxes & fees

9/10 Wonderful! (3,061 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

฿3,688

฿4,385 total

1 Nov - 2 Nov

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

฿4,204

฿4,834 total

1 Nov - 2 Nov

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

฿4,330

฿5,148 total

10 Nov - 11 Nov

includes taxes & fees

Explore a world of travel with Expedia

More ways to book

Book Hotels in Southwest Side on Expedia.com

Find hotels in Southwest Side, IL from ฿2,377

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. Hyatt Place Chicago/Downtown - The Loop

7. Hyatt House Chicago/West Loop-Fulton Market

8. Hilton Chicago

9. Embassy Suites by Hilton Chicago Downtown River North

10. Hampton Inn & Suites Chicago Downtown

11. Hotel Riu Plaza Chicago

12. InterContinental Chicago Magnificent Mile by IHG

13. Homewood Suites by Hilton Chicago Downtown South Loop

14. Radisson Blu Aqua Hotel Chicago

15. L7 Chicago by LOTTE

16. Hyatt Place Chicago/River North

17. Residence Inn Chicago Downtown/Loop

18. Fairfield Inn & Suites Chicago Downtown/River North

19. Hilton Garden Inn Chicago Downtown South Loop

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Hotels recommended for families in Southwest Side

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago-O'Hare International Airport

Hyatt Place Chicago/Downtown - The Loop

Hyatt House Chicago/West Loop-Fulton Market

Embassy Suites by Hilton Chicago Downtown River North

Hilton Chicago

Hilton Vacation Club Hotel Blake Chicago

Homewood Suites by Hilton Chicago Downtown South Loop

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 Royal Sonesta Chicago Downtown

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago O'Hare Airport

Hyatt Regency Chicago

The Godfrey Hotel Chicago

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

Hampton Inn Chicago-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Explore a world of travel with Expedia

Go further with the Expedia app