Book The Best Hotels in Southwest Side, IL for 2026 from CA $100 - 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 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.

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 $191

CA $238 total

includes taxes & fees

Oct 25 - Oct 26

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

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 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.

2. Carlton Inn Midway

Archer Heights

stephen T

CA $139

CA $164 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

3. Rainbow Motel

Garfield Ridge

Jerry

CA $119

CA $139 total

includes taxes & fees

Oct 21 - Oct 22

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

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.

A residential street with a sidewalk, houses, and greenery.

4. Carleton of Oak Park

Oak Park

Brad

CA $173

CA $192 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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.

5. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $173

CA $206 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

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

6. Best Western Grant Park Hotel

Downtown Chicago

Colin

CA $151

CA $180 total

includes taxes & fees

Nov 10 - Nov 11

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A hotel room with a flat-screen TV mounted on a wooden wall, a sofa with a teal pillow, a desk with a lamp, and a coffee maker.

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 hotel room with a large bed, a sofa, a nightstand, a lamp, and a window with curtains.

7. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

CA $243

CA $289 total

includes taxes & fees

Nov 4 - Nov 5

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

A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

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

8. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

CA $203

CA $242 total

includes taxes & fees

Nov 10 - Nov 11

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.

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

9. Hilton Chicago

Downtown Chicago

Anna

CA $239

CA $326 total

includes taxes & fees

Nov 13 - Nov 14

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

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

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

Downtown Chicago

Shanequa

CA $269

CA $369 total

includes taxes & fees

Nov 12 - Nov 13

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

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

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

Ashya

CA $148

CA $176 total

includes taxes & fees

Nov 10 - Nov 11

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

12. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $150

CA $179 total

includes taxes & fees

Nov 11 - Nov 12

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

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

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.

13. Hotel 505 River North

Downtown Chicago

Jordan

CA $242

CA $333 total

includes taxes & fees

Oct 25 - Oct 26

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

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

14. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

CA $227

CA $270 total

includes taxes & fees

Nov 15 - Nov 16

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 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.

15. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Robert

CA $132

CA $160 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

16. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Erin

CA $198

CA $236 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 snack and beverage kiosk with various snacks and drinks.

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.

17. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Shonnette

CA $137

CA $152 total

includes taxes & fees

Oct 26 - Oct 27

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 modern office setup with two monitors, a keyboard, and leather chairs.

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

Downtown Chicago

Brock

CA $269

CA $320 total

includes taxes & fees

Oct 30 - Oct 31

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

A conference room with a long table, chairs, a projector screen, and a carpeted floor.

A large banquet hall with round tables, blue tablecloths, and white chairs with blue sashes.

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

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

CA $201

CA $316 total

includes taxes & fees

Nov 12 - Nov 13

A rooftop terrace with lounge chairs and tables, offering a city skyline view.

A hotel room with a large bed, two armchairs, a wooden dresser, a desk with a chair, a flat-screen TV, and framed pictures on the wall.

A modern bar area with a stainless steel bar counter, multiple stools, a refrigerated display, and a large window offering a view of the city.

A modern office space with two desks, each with a computer monitor, a printer, and a lamp. There is an exit sign on the ceiling.

20. Best Western River North Hotel

Downtown Chicago

Jordan

CA $167

CA $199 total

includes taxes & fees

Nov 9 - Nov 10

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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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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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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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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.

See properties

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

"Stayed for 3 days, and it was great! The staff was super kind when helping me after I accidentally selected the wrong type of room.It was cozy and breakfast was great! I’d stay again 😄"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Cl"

L7 Chicago by LOTTE

10/10 Excellent

"Staff was friendly and helpful! Gave my family and I great ideas for restaurants!"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"Clean room staff was great"

The Royal Sonesta Chicago Downtown

8/10 Good

"."

Fairmont Chicago at Millennium Park

10/10 Excellent

"To quality service from every staff member. Great views. Upgrade to the gold rooms for a wonderful view and access to the lounge. Lounge breakfast and dinner and dessert is WORTH THE $."

The Chicago Hotel Collection River North

10/10 Excellent

"I love that I had my own parking spot with the hotel"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Had a great night in a great room!"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

CA $87

CA $100 total

Oct 26 - Oct 27

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $114

CA $128 total

Oct 25 - Oct 26

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $137

CA $152 total

Oct 26 - Oct 27

includes taxes & fees

9/10 Wonderful! (3,082 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $150

CA $179 total

Nov 11 - Nov 12

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $155

CA $184 total

Nov 1 - Nov 2

includes taxes & fees

8/10 Very good! (1,684 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $175

CA $202 total

Oct 25 - Oct 26

includes taxes & fees

9.4/10 Exceptional! (2,403 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 $100

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 Garden Inn Chicago Downtown South Loop

6. Best Western Grant Park Hotel

7. Hilton Vacation Club Hotel Blake Chicago

8. Homewood Suites by Hilton Chicago Downtown South Loop

9. Hilton Chicago

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

11. Congress Plaza Hotel

12. Travelodge by Wyndham Downtown Chicago

13. Hotel 505 River North

14. Crowne Plaza Chicago West Loop by IHG

15. Hotel Saint Clair- Magnificent Mile

16. Hampton Inn & Suites Chicago Downtown

17. SureStay Plus Hotel by Best Western Chicago Lombard

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

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

20. Best Western River North Hotel

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

S.S. Peter and Paul Church

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection - Magnificent Mile

L7 Chicago by LOTTE

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

The Royal Sonesta Chicago Downtown

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection River North

Hotel Saint Clair- 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

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

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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