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

$141 nightly

$164 total

Nov 8 - Nov 9

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 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

stephen T

$119 nightly

$140 total

Oct 11 - Oct 12

Total with taxes and fees

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

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.

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 12 - Oct 13

Total with taxes and fees

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

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

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.

4. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Oct 21 - Oct 22

Total with taxes and fees

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

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

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

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

5. Hilton Chicago

Downtown Chicago

Anna

$190 nightly

$226 total

Oct 30 - Oct 31

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

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

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

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

$181 nightly

$216 total

Oct 29 - Oct 30

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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

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

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

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

Downtown Chicago

Shanequa

$239 nightly

$284 total

Nov 9 - Nov 10

Total with taxes and fees

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

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

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

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.

8. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

$125 nightly

$149 total

Nov 9 - Nov 10

Total with taxes and fees

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

A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.

A modern restaurant interior with a long counter, booths, and tables.

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

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Corinn

$144 nightly

$171 total

Nov 10 - Nov 11

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 snack and beverage kiosk with various snacks and drinks.

A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

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.

10. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$97 nightly

$107 total

Oct 21 - Oct 22

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

11. Congress Plaza Hotel

Downtown Chicago

Katimah

$116 nightly

$138 total

Nov 10 - Nov 11

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 reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

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

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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.

13. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

$195 nightly

$232 total

Nov 1 - Nov 2

Total with taxes and fees

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$127 nightly

$151 total

Nov 10 - Nov 11

Total with taxes and fees

A spacious living room with a grand piano, a glass coffee table, a sofa, and a couch.

A hotel room with a large bed, a desk with a chair, a lamp, a framed picture on the wall, and a window with blinds.

A historic building with a prominent entrance labeled 'The Tremont Hotel' and a red awning.

A modern living room with a fireplace, a television, and a view of a red brick building.

15. The Tremont Chicago Hotel

Downtown Chicago

John

$107 nightly

$128 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

16. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$122 nightly

$144 total

Nov 10 - Nov 11

Total with taxes and fees

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 grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.

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

17. Palmer House a Hilton Hotel

Downtown Chicago

Christy

$215 nightly

$256 total

Oct 31 - Nov 1

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 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.

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

18. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

ARLEEN

$142 nightly

$168 total

Nov 2 - Nov 3

Total with taxes and fees

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

A hotel room with a bed, a TV, a window with curtains, and a view of tall buildings.

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.

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

$179 nightly

$212 total

Nov 1 - Nov 2

Total with taxes and fees

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 gym with treadmills, weight machines, and kettlebells.

A conference room with rows of chairs, a large window with a view of buildings, and a ceiling with recessed lighting.

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

Downtown Chicago

Brock

$236 nightly

$280 total

Oct 30 - Oct 31

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

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"We were on the 3rd floor, which was very quiet. Our room was nice and comfortable. It's downtown so parking is a challenge. When choosing this hotel, I read that there was on site parking for $58 a night. I was fine with that but when we checked in, I was told that there was no in/out allowed. So, we paid $82 per night for valet parking. We checked in around 9pm. The lobby was fairly empty but there was a DJ playing very loud music. I had trouble hearing what the front desk clerk was saying to me, especially when explaining the parking situation. We would stay there again as the location was perfect for walking to the Harry Potter Store!"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Loved staying here! Rooms are smaller but perfect amenities. Pillows are the perfect fluffiness not lumpy. The sheets were silky. Espresso machine was devine. Price very competitive. A short walk to Michigan avenue. Would stay here everytime I am in town."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"I will always stay here at Royal as it was the best experience I have ever had from all my travels Staff is stellar and a breakfast !!! Bravo bravo!!!"

Hilton Chicago O'Hare Airport

8/10 Good

"It was nice."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Nice updated property in a great location"

Sports Illustrated Resorts Chicago

10/10 Excellent

"Great Staff, good communication, & had a shuttle bus for concert!"

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"

Hilton Chicago

10/10 Excellent

"Clean room and convenient to city walk."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"This was my second time staying and it was wonderful."

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 20 - Oct 21

Total with taxes and fees

6.8/10 (2,355 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 17 - Oct 18

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$97 nightly

$107 total

Oct 21 - Oct 22

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

8/10 Very Good! (1,661 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$122 nightly

$144 total

Nov 10 - Nov 11

Total with taxes and fees

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

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 Chicago

6. Hilton Vacation Club Hotel Blake Chicago

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

8. Best Western Grant Park Hotel

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. SureStay Plus Hotel by Best Western Chicago Lombard

11. Congress Plaza Hotel

12. Hampton Inn Chicago-O'Hare International Airport

13. Hyatt House Chicago/West Loop-Fulton Market

14. Hilton Garden Inn Chicago Downtown South Loop

15. The Tremont Chicago Hotel

16. Travelodge by Wyndham Downtown Chicago

17. Palmer House a Hilton Hotel

18. Hotel Saint Clair- Magnificent Mile

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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

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

The Chicago Hotel Collection - Magnificent Mile

Hotel Saint Clair- Magnificent Mile

The Royal Sonesta Chicago Downtown

Hilton Chicago O'Hare Airport

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Sports Illustrated Resorts Chicago

The Godfrey Hotel Chicago

Hilton Chicago

InterContinental Chicago Magnificent Mile by IHG

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

Explore a world of travel with Expedia

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