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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

CA $190

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 flat-screen TV mounted above a fireplace, flanked by two potted plants.

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.

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 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 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 $118

CA $139 total

includes taxes & fees

Oct 22 - Oct 23

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

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

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

CA $242

CA $288 total

includes taxes & fees

Nov 4 - Nov 5

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 residential street with a sidewalk, houses, and greenery.

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 $173

CA $192 total

includes taxes & fees

Oct 27 - Oct 28

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

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.

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

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

6. Hotel 505 River North

Downtown Chicago

Jordan

CA $233

CA $322 total

includes taxes & fees

Nov 20 - Nov 21

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

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.

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

7. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $173

CA $205 total

includes taxes & fees

Nov 9 - Nov 10

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.

8. Best Western Grant Park Hotel

Downtown Chicago

Colin

CA $151

CA $180 total

includes taxes & fees

Nov 10 - Nov 11

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

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

CA $203

CA $242 total

includes taxes & fees

Nov 10 - Nov 11

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

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

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

Downtown Chicago

Shanequa

CA $273

CA $374 total

includes taxes & fees

Nov 12 - Nov 13

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

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

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

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

11. Hilton Chicago

Downtown Chicago

Anna

CA $239

CA $326 total

includes taxes & fees

Nov 20 - Nov 21

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.

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.

12. Congress Plaza Hotel

Downtown Chicago

Ashya

CA $147

CA $175 total

includes taxes & fees

Nov 10 - Nov 11

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

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.

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

13. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $150

CA $179 total

includes taxes & fees

Nov 11 - Nov 12

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

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.

A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

14. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

CA $227

CA $269 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 modern interior with a dining area, sofas, and artwork on the walls.

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

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

15. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Robert

CA $132

CA $159 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 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.

16. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Shonnette

CA $137

CA $152 total

includes taxes & fees

Oct 27 - Oct 28

A building with a stone facade and large glass windows.

A room with a large window, a patterned armchair, and a view of a cityscape with buildings and a street.

A hotel room with a large bed, two bedside tables with lamps, a chair, and a city view through large windows.

A balcony with outdoor seating, overlooking a busy street with cars and buildings.

17. Ohio House Motel

Downtown Chicago

John

CA $154

CA $181 total

includes taxes & fees

Nov 15 - Nov 16

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 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.

18. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Erin

CA $210

CA $250 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.

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

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

CA $198

CA $311 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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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.

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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 Riu Plaza Chicago

10/10 Excellent

"Super clean, the waitstaff is amazing. The breakfast buffet is unreal."

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"My stay was very nice here at this hotel. The staff were very helpful and polite. My room was okay with a nice view of the city but it had an unpleasant smell in the room and some of the wall paper was peeling. I still would say I’d stay here again. It was not horrible at all. 4 stars from me."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great location, clean rooms, great staff… and it smelled so good every time we walked into the hotel."

L7 Chicago by LOTTE

10/10 Excellent

"Friendly staff, huge rooms and an amazing location, will stay here again!"

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 😄"

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

Nov 2 - Nov 3

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $114

CA $128 total

Oct 29 - Oct 30

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $137

CA $152 total

Oct 27 - Oct 28

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $150

CA $179 total

Nov 11 - Nov 12

includes taxes & fees

7.8/10 Good! (2,930 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $155

CA $184 total

Nov 2 - Nov 3

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 $201 total

Oct 25 - Oct 26

includes taxes & fees

Hotels in Southwest Side with star rating

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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. Hilton Vacation Club Hotel Blake Chicago

5. Carleton of Oak Park

6. Hotel 505 River North

7. Hilton Garden Inn Chicago Downtown South Loop

8. Best Western Grant Park Hotel

9. Homewood Suites by Hilton Chicago Downtown South Loop

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

11. Hilton Chicago

12. Congress Plaza Hotel

13. Travelodge by Wyndham Downtown Chicago

14. Crowne Plaza Chicago West Loop by IHG

15. Hotel Saint Clair- Magnificent Mile

16. SureStay Plus Hotel by Best Western Chicago Lombard

17. Ohio House Motel

18. Hampton Inn & Suites Chicago Downtown

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

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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

Hotel Riu Plaza Chicago

The Chicago Hotel Collection - Magnificent Mile

The Royal Sonesta Chicago Downtown

L7 Chicago by LOTTE

The Chicago Hotel Collection Ambassador Gold Coast

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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