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 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.

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

CA $186

CA $233 total

includes taxes & fees

Nov 9 - Nov 10

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 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 13 - Oct 14

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

3. Rainbow Motel

Garfield Ridge

Jerry

CA $99

CA $117 total

includes taxes & fees

Oct 14 - Oct 15

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

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

CA $174

CA $193 total

includes taxes & fees

Oct 12 - Oct 13

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.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

CA $258

CA $307 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

CA $236

CA $322 total

includes taxes & fees

Oct 30 - Oct 31

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

7. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

CA $178

CA $212 total

includes taxes & fees

Nov 9 - Nov 10

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 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.

8. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $156

CA $185 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Corinn

CA $216

CA $257 total

includes taxes & fees

Nov 9 - Nov 10

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 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.

10. Hotel 505 River North

Downtown Chicago

Giana

CA $269

CA $366 total

includes taxes & fees

Nov 8 - Nov 9

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.

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.

11. Congress Plaza Hotel

Downtown Chicago

Katimah

CA $165

CA $197 total

includes taxes & fees

Nov 5 - Nov 6

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

A hotel reception area with a black counter, a chandelier, a television, and a floral wallpaper.

A hallway with a patterned carpet, a chandelier, and a neon sign.

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

12. The Tremont Chicago Hotel

Downtown Chicago

"The room smelled of paint and wallpaper glue so strongly it made my nose run. Additionally, the controls for the wall were ancient and hard to use in the dark. There were open holes in the wall with cords running in them, grimy bathroom corners, and cracked door frames for the bathroom. The entrance seems nice, until you get to the rooms. The front desk wasn’t staffed when I tried to check out in the morning. After waiting for 5 minutes, I dropped my room key and left."

Seth

CA $141

CA $182 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

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

Downtown Chicago

Shanequa

CA $279

CA $381 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $181

CA $215 total

includes taxes & fees

Nov 9 - Nov 10

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

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

15. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

CA $199

CA $237 total

includes taxes & fees

Nov 1 - Nov 2

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

CA $190

CA $229 total

includes taxes & fees

Nov 2 - Nov 3

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.

17. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

CA $277

CA $330 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 hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

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.

18. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

CA $138

CA $153 total

includes taxes & fees

Oct 22 - Oct 23

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

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.

19. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

CA $164

CA $195 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

A person overlooking a cityscape from a high vantage point.

20. Palmer House a Hilton Hotel

Downtown Chicago

Christy

CA $271

CA $365 total

includes taxes & fees

Oct 31 - Nov 1

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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 Ambassador Gold Coast

10/10 Excellent

"It was way more that i expected, ample rooms, clean and well lighted, and don’t mention the location, it was great experience. 👍"

Hilton Chicago O'Hare Airport

10/10 Excellent

"Expensive, however, you are paying for convenience. For us it is well worth it. The staff is professional and friendly. The restaurant (Andiamo) is 5 stars, we look forward to eating there every time we stay."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Great staff and excellent location!"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great hotel, good location."

Congress Plaza Hotel

10/10 Excellent

"For a last minute booking they were very nice and helpful"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Breakfast is a buffet and was great!!! The breakfast blew my mind with how many options they had as well. Out of all of the resorts and hotels I’ve stayed at, the food blew the others out of the park. Never have seen so many options. Staff help was also excellent. The rooftop bar is a must do. The view was beautiful and is the tallest rooftop lounge in Chicago. Booking through Expedia is the way to go with this hotel for sure!!"

Eurostars Magnificent Mile

10/10 Excellent

"A"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

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

Freehand Chicago

10/10 Excellent

"Great great great great ."

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 22 - Oct 23

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $115

CA $129 total

Oct 15 - Oct 16

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $138

CA $153 total

Oct 22 - Oct 23

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $155

CA $185 total

Nov 1 - Nov 2

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $156

CA $185 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (2,890 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $178

CA $204 total

Nov 1 - Nov 2

includes taxes & fees

Hotels in Southwest Side with star rating

Explore a world of travel with Expedia

Things to do in Chicago

Book Hotels in Southwest Side on Expedia.com

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. Carleton of Oak Park

5. Hilton Vacation Club Hotel Blake Chicago

6. Hilton Chicago

7. Best Western Grant Park Hotel

8. Travelodge by Wyndham Downtown Chicago

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Hotel 505 River North

11. Congress Plaza Hotel

12. The Tremont Chicago Hotel

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

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hampton Inn & Suites Chicago Downtown

16. Hotel Saint Clair- Magnificent Mile

17. Hyatt House Chicago/West Loop-Fulton Market

18. SureStay Plus Hotel by Best Western Chicago Lombard

19. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

20. Palmer House a Hilton Hotel

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 Ambassador Gold Coast

Hilton Chicago O'Hare Airport

Hotel Saint Clair- Magnificent Mile

Fairmont Chicago at Millennium Park

Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

Eurostars Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

Freehand 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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