Southwest Side Hotel & Accommodation Deals 2026 from NZ$126 - Fully Refundable Options

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

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

NZ$292

includes taxes & fees

8 Nov - 9 Nov

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

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 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.

2. Carlton Inn Midway

Archer Heights

stephen T

NZ$219

includes taxes & fees

13 Oct - 14 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 compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

3. Rainbow Motel

Garfield Ridge

Jerry

NZ$146

includes taxes & fees

12 Oct - 13 Oct

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

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

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

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

NZ$384

includes taxes & fees

29 Oct - 30 Oct

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 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.

5. Carleton of Oak Park

Oak Park

Brad

NZ$242

includes taxes & fees

12 Oct - 13 Oct

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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

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

6. Hilton Chicago

Downtown Chicago

Anna

NZ$403

includes taxes & fees

30 Oct - 31 Oct

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

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

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

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

7. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

NZ$265

includes taxes & fees

9 Nov - 10 Nov

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

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

8. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

NZ$268

includes taxes & fees

10 Nov - 11 Nov

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.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Corinn

NZ$304

includes taxes & fees

10 Nov - 11 Nov

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

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.

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.

10. Hotel 505 River North

Downtown Chicago

Giana

NZ$457

includes taxes & fees

8 Nov - 9 Nov

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.

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

Downtown Chicago

Shanequa

NZ$509

includes taxes & fees

9 Nov - 10 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 Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

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

12. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

NZ$256

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

A modern interior with a long counter, glass partitions, and a brick wall backdrop.

13. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

NZ$413

includes taxes & fees

1 Nov - 2 Nov

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

A laundry area with a washing machine, a dryer, and an ice dispenser.

A person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.

A modern interior with a dining area, sofas, and artwork on the walls.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

ARLEEN

NZ$270

includes taxes & fees

2 Nov - 3 Nov

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

A restaurant with booths, tables, and a green wall in the background.

A compact kitchen with a microwave, coffee maker, and sink.

A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

15. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

NZ$259

includes taxes & fees

10 Nov - 11 Nov

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

16. Congress Plaza Hotel

Downtown Chicago

Ashya

NZ$246

includes taxes & fees

10 Nov - 11 Nov

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

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

A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.

A person overlooking a cityscape from a high vantage point.

17. Palmer House a Hilton Hotel

Downtown Chicago

Christy

NZ$456

includes taxes & fees

31 Oct - 1 Nov

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

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

18. Hotel Riu Plaza Chicago

Downtown Chicago

Kevin

NZ$403

includes taxes & fees

2 Nov - 3 Nov

A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

A conference room with a long table, chairs, a projector screen, and a television on the wall.

A hotel room with two beds, a desk with a television, a chair, a ceiling fan, and a window with a view of a building.

19. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Downtown Chicago

Brock

NZ$497

includes taxes & fees

30 Oct - 31 Oct

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

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

20. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

NZ$244

includes taxes & fees

2 Nov - 3 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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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

Recent Reviews in Southwest Side

Sports Illustrated Resorts Chicago

10/10 Excellent

"Since Our flight kept being delayed; we arrived very early next day. We notified the front desk when this was happening. Upon our arrival, we were greeted with a friendly front desk person. Our room was ready. The room was spacious. It was beautiful. Staff in the front desk were very friendly and helpful."

River Hotel

10/10 Excellent

"Great hotel"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Perfect location. Everything within walking distance. Bar was amazing"

Eurostars Magnificent Mile

10/10 Excellent

"Great location, clean rooms, super kind staff."

Hilton Chicago

10/10 Excellent

"I enjoyed the property's elegance and location, with all the sightseeing sites within walking distance of the hotel. I also enjoyed the Irish pub and restaurant in the main lobby."

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great location. Rooms are very comfortable, clean, and luxurious. Had a great sister's weekend at this location!"

The Godfrey Hotel Chicago

10/10 Excellent

"The property was well maintained. The front desk staff was always friendly and helpful. The valet parking was definitely expensive and overall we had a great stay"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Clean, quiet, comfortable, convenient with great check-in service. Affordable. Great location. All you need."

More cheap accommodation in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

NZ$126

20 Oct - 21 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

NZ$161

17 Oct - 18 Oct

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

NZ$191

21 Oct - 22 Oct

includes taxes & fees

9/10 Wonderful! (3,064 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

NZ$231

1 Nov - 2 Nov

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

NZ$256

1 Nov - 2 Nov

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

NZ$259

10 Nov - 11 Nov

includes taxes & fees

Explore a world of travel with Expedia

Book Hotels in Southwest Side on Expedia.com

Search Southwest Side hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Southwest Side

Check prices for these dates

Filter by

Property class

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. Carleton of Oak Park

6. Hilton Chicago

7. Best Western Grant Park Hotel

8. Hilton Garden Inn Chicago Downtown South Loop

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Hotel 505 River North

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

12. Hampton Inn Chicago-O'Hare International Airport

13. Hyatt House Chicago/West Loop-Fulton Market

14. Hotel Saint Clair- Magnificent Mile

15. Travelodge by Wyndham Downtown Chicago

16. Congress Plaza Hotel

17. Palmer House a Hilton Hotel

18. Hotel Riu Plaza Chicago

19. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

20. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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

Recent Reviews in Southwest Side

Sports Illustrated Resorts Chicago

River Hotel

InterContinental Chicago Magnificent Mile by IHG

Eurostars Magnificent Mile

Hilton Chicago

Fairmont Chicago at Millennium Park

The Godfrey Hotel Chicago

Club Quarters Hotel, Central Loop, Chicago

More cheap accommodation 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

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