Top 10 Hotels in Southwest Side (from $71) 2026 - Competitive Prices

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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 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

$149 nightly

$173 total

Oct 25 - Oct 26

Total with taxes and fees

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 flat-screen TV mounted above a fireplace, flanked by two potted plants.

2. Carlton Inn Midway

Archer Heights

Icaro

$119 nightly

$140 total

Oct 7 - Oct 8

Total with taxes and fees

A bedroom with a bed, a wall-mounted air conditioner, and a wooden floor.

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

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.

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 7 - Oct 8

Total with taxes and fees

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

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

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

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

4. Carleton of Oak Park

Oak Park

Brad

$114 nightly

$127 total

Oct 27 - Oct 28

Total with taxes and fees

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

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

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.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$172 nightly

$204 total

Nov 3 - Nov 4

Total with taxes and fees

A large, historic building with a central courtyard surrounded by trees.

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

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

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

6. Hilton Chicago

Downtown Chicago

Anna

$193 nightly

$227 total

Oct 30 - Oct 31

Total with taxes and fees

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

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

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

$161 nightly

$192 total

Oct 25 - Oct 26

Total with taxes and fees

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

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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.

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

Downtown Chicago

Shanequa

$258 nightly

$307 total

Nov 1 - Nov 2

Total with taxes and fees

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.

A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

A snack and beverage kiosk with various snacks and drinks.

9. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$93 nightly

$104 total

Oct 7 - Oct 8

Total with taxes and fees

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

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

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

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

10. Congress Plaza Hotel

Downtown Chicago

Katimah

$107 nightly

$127 total

Nov 2 - Nov 3

Total with taxes and fees

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

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

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

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

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$112 nightly

$131 total

Nov 2 - Nov 3

Total with taxes and fees

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 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.

12. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

$182 nightly

$216 total

Oct 25 - Oct 26

Total with taxes and fees

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.

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.

13. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

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.

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

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$184 nightly

$219 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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

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

15. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$193 nightly

$229 total

Nov 1 - Nov 2

Total with taxes and fees

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 hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.

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

16. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$128 nightly

$152 total

Nov 2 - Nov 3

Total with taxes and fees

A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

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

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

A grand hall with a central aisle, ornate chandeliers, and rows of chairs.

17. Palmer House a Hilton Hotel

Downtown Chicago

Sydney

$218 nightly

$256 total

Oct 31 - Nov 1

Total with taxes and fees

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

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

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

$109 nightly

$130 total

Nov 2 - Nov 3

Total with taxes and fees

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.

A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

An indoor swimming pool with lounge chairs and a no diving sign.

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Patricia

$164 nightly

$220 total

Nov 1 - Nov 2

Total with taxes and fees

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.

A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

A spacious lobby with a seating area, a reception desk, and a large screen.

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Tommy

$156 nightly

$185 total

Oct 25 - Oct 26

Total with taxes and fees

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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 scene.

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Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area, or check out 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

Congress Plaza Hotel

8/10 Good

"Great to stay for the historical aspects of the building. Great lobby. Nice restaurant option. Room was dated and painted. Nice size. Bathroom and room could use a renovation, but to do the whole building would be a big investment. There is a reason the rates are lower compared to nearby hotels, but the place was clean, historical, and functional."

Hilton Chicago

10/10 Excellent

"Everything about my stay at the Hilton was excellent and truly amazing. The quality of the entire experience was outstanding. The only drawback was that the room wasn't cleaned daily, and amenities like shampoo, conditioner, towels, and toilet paper weren't replenished regularly. Aside from this, everything was wonderful and highly recommended."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Hollywood glam type hotel! Gorgeous and built in the 1920’s. So modern upscale items were not there (usb connector in room) but it was still lovely! Definitely recommend"

Hilton Chicago O'Hare Airport

10/10 Excellent

"Usually stay here a couple times a year, always a good experience."

The Wade

8/10 Good

"Great location with great view of Lakefront. Building however feels dated and premises could use a facelift with a refresh of amenities and suites."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"very helpful staff, large rest areas for waiting, good price, convenient location. A nice no-frills restaurant and bar onsite. Best choice for an Unpretentious visit stay."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great location, good sized rooms, comfortable beds"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

$62 nightly

$71 total

Oct 14 - Oct 15

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 13 - Oct 14

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$93 nightly

$104 total

Oct 7 - Oct 8

Total with taxes and fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$109 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$112 nightly

$131 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (2,887 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

9.4/10 Exceptional! (2,396 reviews)

Hotels in Southwest Side with star-rating

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Things to do in Chicago

Find hotels in Southwest Side, IL from $71

Upfront pricing

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. Carleton of Oak Park

5. Hilton Vacation Club Hotel Blake Chicago

6. Hilton Chicago

7. Best Western Grant Park Hotel

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

9. SureStay Plus Hotel by Best Western Chicago Lombard

10. Congress Plaza Hotel

11. Travelodge by Wyndham Downtown Chicago

12. Homewood Suites by Hilton Chicago Downtown South Loop

13. Hampton Inn Chicago-O'Hare International Airport

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hyatt House Chicago/West Loop-Fulton Market

16. Hotel Saint Clair- Magnificent Mile

17. Palmer House a Hilton Hotel

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

20. Crowne Plaza Chicago West Loop by IHG

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

Congress Plaza Hotel

Hilton Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago O'Hare Airport

The Wade

Club Quarters Hotel, Central Loop, Chicago

The Chicago Hotel Collection - Magnificent Mile

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

Hotels in Southwest Side with star-rating

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