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 reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

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 $186

CA $233 total

includes taxes & fees

Nov 8 - Nov 9

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

Icaro

CA $149

CA $175 total

includes taxes & fees

Oct 26 - Oct 27

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 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 kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

3. Rainbow Motel

Garfield Ridge

Jerry

CA $99

CA $117 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

4. Carleton of Oak Park

Oak Park

Brad

CA $157

CA $174 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 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

CA $244

CA $290 total

includes taxes & fees

Nov 3 - Nov 4

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

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 $322 total

includes taxes & fees

Oct 30 - Oct 31

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

7. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

CA $229

CA $272 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

8. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $164

CA $195 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 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 hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.

9. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

CA $158

CA $191 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 spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

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

10. Congress Plaza Hotel

Downtown Chicago

Katimah

CA $165

CA $196 total

includes taxes & fees

Nov 2 - Nov 3

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

11. 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 $126

CA $164 total

includes taxes & fees

Oct 27 - Oct 28

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.

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

CA $259

CA $308 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 waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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

Downtown Chicago

Shanequa

CA $327

CA $437 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

CA $262

CA $311 total

includes taxes & fees

Oct 25 - Oct 26

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.

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

15. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

CA $178

CA $205 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

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

16. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

CA $212

CA $252 total

includes taxes & fees

Nov 5 - Nov 6

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.

17. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

CA $155

CA $184 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

18. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

CA $275

CA $327 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen area with a white countertop, wooden cabinets, and various appliances including a toaster, a coffee maker, and a sandwich press.

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

19. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

CA $138

CA $153 total

includes taxes & fees

Oct 26 - Oct 27

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.

A modern lounge area with a sofa, chairs, and a large potted plant.

A spacious indoor area with seating arrangements, large windows, and indoor plants.

20. The Emily Hotel

Downtown Chicago

Leslie

CA $234

CA $278 total

includes taxes & fees

Nov 1 - Nov 2

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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

Hilton Chicago

10/10 Excellent

"Our stay at the Hilton Chicago was excellent.The rooms were clean,staff very professional,and food was excellent."

The Godfrey Hotel Chicago

8/10 Good

"It was a great stay except for the fact that the toilet in the room made a lot of noise when it wasn’t being used - every 45 min or so it would make a loud noise"

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is in a nice neighborhood and the room was clean. The bed and toilet were both very low to the ground, and there were very few electrical outlets, but otherwise it was a pleasant stay."

Hilton Chicago O'Hare Airport

10/10 Excellent

"Excellent staff and friendly helpful. Excellent stay and will stay again."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Staff was amazing!! They were all so kind and attentive! I enjoyed my stay so much and I’m looking on planning another trip just to stay at this hotel!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"CQ is a reliable brand as this property demonstrated. I was particularly pleased with the size of the room and fitness facility. Best CQ I have stayed at and would return. Two quibbles: No desk lamp, therefore a dark work area and no hand soap (use body gel? I bring my own). Housekeeping excellent."

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 27 - Oct 28

includes taxes & fees

6.8/10 (2,350 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $115

CA $128 total

Oct 16 - Oct 17

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $138

CA $153 total

Oct 26 - Oct 27

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! (1,656 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $164

CA $195 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

9.4/10 Exceptional! (2,394 reviews)

Hotels in Southwest Side with star rating

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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. Hotel Saint Clair- Magnificent Mile

10. Congress Plaza Hotel

11. The Tremont Chicago Hotel

12. Homewood Suites by Hilton Chicago Downtown South Loop

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

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hampton Inn Chicago-O'Hare International Airport

16. Crowne Plaza Chicago West Loop by IHG

17. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

18. Hyatt House Chicago/West Loop-Fulton Market

19. SureStay Plus Hotel by Best Western Chicago Lombard

20. The Emily 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

Hilton Chicago

The Godfrey Hotel Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago O'Hare Airport

The Royal Sonesta Chicago Downtown

Club Quarters Hotel, Central Loop, 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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