Top 10 Hotels in Southwest Side (from $71) 2026 - Competitive Prices

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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 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 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

Ashima

$141 nightly

$164 total

Nov 1 - Nov 2

Total with taxes and fees

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 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

Icaro

$119 nightly

$140 total

Oct 4 - Oct 5

Total with taxes and fees

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

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 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

$93 nightly

$109 total

Oct 2 - Oct 3

Total with taxes and fees

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

4. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Oct 15 - Oct 16

Total with taxes and fees

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.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$181 nightly

$216 total

Oct 29 - Oct 30

Total with taxes and fees

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.

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

Downtown Chicago

Shanequa

$240 nightly

$285 total

Oct 4 - Oct 5

Total with taxes and fees

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.

7. Hilton Chicago

Downtown Chicago

Alan

$190 nightly

$226 total

Oct 30 - Oct 31

Total with taxes and fees

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.

8. Congress Plaza Hotel

Downtown Chicago

Guadalupe

$125 nightly

$149 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

9. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$188 nightly

$223 total

Oct 25 - Oct 26

Total with taxes and fees

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.

10. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

$195 nightly

$229 total

Oct 31 - Nov 1

Total with taxes and fees

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 compact kitchen with a microwave, coffee maker, and sink.

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$120 nightly

$141 total

Nov 1 - Nov 2

Total with taxes and fees

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 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.

12. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Michael

$104 nightly

$116 total

Oct 4 - Oct 5

Total with taxes and fees

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 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.

13. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

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.

A modern gym with various exercise equipment, large windows, and a city view.

14. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$178 nightly

$212 total

Nov 1 - Nov 2

Total with taxes and fees

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

A modern hotel lobby with multiple dining areas, a central food station, and a high-ceiling atrium with balconies.

A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.

A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Patricia

$186 nightly

$221 total

Nov 1 - Nov 2

Total with taxes and fees

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

A hotel room with a large window, a bed, and a suitcase.

A modern living room with a fireplace, leather sofas, and a wooden floor.

16. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Julian

$101 nightly

$120 total

Nov 1 - Nov 2

Total with taxes and fees

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 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.

17. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$145 nightly

$172 total

Nov 1 - Nov 2

Total with taxes and fees

A spacious lobby with a central coffee table, sofas, and a large mirror.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

18. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Marta

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

19. The Wade

Downtown Chicago

Erin

$127 nightly

$151 total

Nov 1 - Nov 2

Total with taxes and fees

An outdoor seating area with sofas and tables, surrounded by greenery and modern buildings in the background.

A modern hotel with a glass facade, multiple floors, and a prominent sign.

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 hotel lobby with multiple round tables, comfortable seating, a large window offering a city view, and a contemporary art piece on the wall.

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

Downtown Chicago

Brock

$231 nightly

$274 total

Oct 30 - Oct 31

Total with taxes and fees

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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

Eurostars Magnificent Mile

10/10 Excellent

"Great location, incredible staff, very clean, nice and safe. Incredible value!!!!!"

L7 Chicago by LOTTE

10/10 Excellent

"Great room, super comfy bed, air filter in the room and no issues with fragrance. Nespresso, kettle and fridge in the room and a coffee machine downstairs in the lobby"

River Hotel

10/10 Excellent

"Excellent location and great views! Will be back!"

Hilton Chicago

8/10 Good

"Having a Starbucks on property was very helpful! Good location and incredibly helpful staff."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Excellent location!"

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"Nice place! Perfect location!"

Fairmont Chicago at Millennium Park

10/10 Excellent

"An amazing location for Chicago and a beautiful hotel"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."

Central Loop Hotel

10/10 Excellent

"I liked the location and staff"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

$62 nightly

$71 total

Oct 14 - Oct 15

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 8 - Oct 9

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$104 nightly

$116 total

Oct 4 - Oct 5

Total with taxes and fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$109 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,641 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$120 nightly

$141 total

Nov 1 - Nov 2

Total with taxes and fees

7.8/10 Good! (2,872 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

Hotels in Southwest Side with star-rating

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Things to do in Chicago

Find hotels in Southwest Side, IL from $71

Upfront pricing

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. Sable at Navy Pier Chicago, Curio Collection by Hilton

7. Hilton Chicago

8. Congress Plaza Hotel

9. Hilton Garden Inn Chicago Downtown South Loop

10. Homewood Suites by Hilton Chicago Downtown South Loop

11. Travelodge by Wyndham Downtown Chicago

12. SureStay Plus Hotel by Best Western Chicago Lombard

13. Hampton Inn Chicago-O'Hare International Airport

14. Hyatt House Chicago/West Loop-Fulton Market

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

16. Club Quarters Hotel, Central Loop, Chicago

17. Crowne Plaza Chicago West Loop by IHG

18. The Chicago Hotel Collection Ambassador Gold Coast

19. The Wade

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

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

Eurostars Magnificent Mile

L7 Chicago by LOTTE

River Hotel

Hilton Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hampton Inn Chicago Downtown/Magnificent Mile

Fairmont Chicago at Millennium Park

The Royal Sonesta Chicago Downtown

Central Loop Hotel

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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