Book The Best Hotels in Southwest Side, IL for 2026 from CA $101 - Fully Refundable Options

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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 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.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

CA $187

CA $233 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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

CA $149

CA $175 total

includes taxes & fees

Oct 6 - Oct 7

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

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.

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

3. Rainbow Motel

Garfield Ridge

Jerry

CA $119

CA $140 total

includes taxes & fees

Oct 6 - Oct 7

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.

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.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

CA $245

CA $291 total

includes taxes & fees

Nov 3 - Nov 4

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

5. Carleton of Oak Park

Oak Park

Brad

CA $160

CA $178 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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

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

6. Hilton Chicago

Downtown Chicago

Anna

CA $236

CA $323 total

includes taxes & fees

Oct 30 - Oct 31

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

A modern interior with wooden flooring, black furniture, and large windows offering city views.

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

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

7. Hotel 505 River North

Downtown Chicago

Giana

CA $326

CA $434 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

8. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

CA $158

CA $191 total

includes taxes & fees

Nov 2 - Nov 3

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.

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

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

9. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

CA $178

CA $205 total

includes taxes & fees

Nov 1 - Nov 2

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

10. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $157

CA $187 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

11. Congress Plaza Hotel

Downtown Chicago

Jessica

CA $164

CA $194 total

includes taxes & fees

Nov 2 - Nov 3

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 spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

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

Downtown Chicago

Shanequa

CA $326

CA $437 total

includes taxes & fees

Nov 1 - Nov 2

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

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

13. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

CA $139

CA $155 total

includes taxes & fees

Oct 6 - Oct 7

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.

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.

14. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

CA $271

CA $323 total

includes taxes & fees

Oct 25 - Oct 26

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.

15. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $269

CA $320 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a marble island, fruit bowls, and a city view.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

16. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

CA $241

CA $337 total

includes taxes & fees

Oct 31 - Nov 1

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 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.

17. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

CA $275

CA $327 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

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

18. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

CA $331

CA $418 total

includes taxes & fees

Oct 31 - Nov 1

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

A modern hotel with a corner location, large windows, and a green awning.

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

19. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

CA $197

CA $235 total

includes taxes & fees

Nov 1 - Nov 2

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.

20. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

CA $165

CA $197 total

includes taxes & fees

Nov 2 - Nov 3

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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

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Mom & daughter trip to meet in Chicago to see a concert. Lovely property in a good location to get everywhere we needed. Felt safe walking around day & night as needed."

Hilton Chicago

8/10 Good

"Solid 4 out of 5 star hotel. Great location and helpful staff. No room service keeps it from 5 star territory."

Congress Plaza Hotel

10/10 Excellent

"If you’re going to a bears game this place is amazing. About a 25 minute walk not horrible, bed was comfortable room was clean. Not haunted at all despite the rumors. Overall a great experience."

Hotel Riu Plaza Chicago

10/10 Excellent

"We had a good experience, nothing to complain!"

The Wade

10/10 Excellent

"Everything was super clean They made the bed everyday and made sure we had fresh towels. Every time we went into the elevator the staff was very friendly and even asked how our day was going or did we slept well"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Good place"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Clean sensible hotel. Can’t beat location."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Really nice place"

Sports Illustrated Resorts Chicago

8/10 Good

"Nice room and great location…need a restaurant and real bar-bar is sort of open…would like to see it after they really rebrand everything"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

CA $88

CA $101 total

Oct 14 - Oct 15

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $115

CA $129 total

Oct 11 - Oct 12

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $139

CA $155 total

Oct 6 - Oct 7

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $156

CA $185 total

Nov 1 - Nov 2

includes taxes & fees

8/10 Very good! (1,653 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $157

CA $187 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (2,885 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $178

CA $205 total

Nov 1 - Nov 2

includes taxes & fees

Hotels in Southwest Side with star rating

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Find hotels in Southwest Side, IL from CA $101

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. Carleton of Oak Park

6. Hilton Chicago

7. Hotel 505 River North

8. Hotel Saint Clair- Magnificent Mile

9. Hampton Inn Chicago-O'Hare International Airport

10. Travelodge by Wyndham Downtown Chicago

11. Congress Plaza Hotel

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

13. SureStay Plus Hotel by Best Western Chicago Lombard

14. Homewood Suites by Hilton Chicago Downtown South Loop

15. Hilton Garden Inn Chicago Downtown South Loop

16. Fairmont Chicago at Millennium Park

17. Hyatt House Chicago/West Loop-Fulton Market

18. Le Méridien Essex Chicago

19. Hampton Inn & Suites Chicago Downtown

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

Hotel Saint Clair- Magnificent Mile

Hilton Chicago

Congress Plaza Hotel

Hotel Riu Plaza Chicago

The Wade

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

InterContinental Chicago Magnificent Mile by IHG

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Sports Illustrated Resorts 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

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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