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 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 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 modern lobby with a vending machine, a statue, and an exit sign.

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 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.

A reception area with a wooden reception desk, a sofa, and a coffee table.

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 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

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

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

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

$112 nightly

$124 total

Oct 12 - Oct 13

Total with taxes and fees

A large, historic building with a central courtyard surrounded by trees.

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

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.

5. Hilton Chicago

Downtown Chicago

Alan

$190 nightly

$226 total

Oct 30 - Oct 31

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 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.

6. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$184 nightly

$219 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.

A modern restaurant interior with a long counter, booths, and tables.

7. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

$195 nightly

$231 total

Oct 31 - Nov 1

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

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

Downtown Chicago

Shanequa

$328 nightly

$390 total

Oct 29 - Oct 30

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.

9. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$191 nightly

$227 total

Nov 1 - Nov 2

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 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

Guadalupe

$125 nightly

$149 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 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 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.

11. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

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

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.

12. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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

$118 nightly

$139 total

Nov 1 - Nov 2

Total with taxes and fees

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

A modern hotel room with a large bed, a desk, a chair, a lamp, and a view of the city through large windows.

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

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

14. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

$247 nightly

$294 total

Nov 1 - Nov 2

Total with taxes and fees

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

A hotel room with a large bed, a bedside table with a lamp, a small table, a chair, and a view of a building through the window.

A conference room with rows of chairs, a large window with a view of buildings, and a ceiling with recessed lighting.

A modern living room with a large bookshelf, a sofa, a coffee table, and a view of the cityscape.

15. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Terri

$216 nightly

$257 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 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 modern gym with various exercise equipment, large windows, and a city view.

16. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$178 nightly

$212 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 room with a large window, a sofa, a small table, and a kitchen area with wine bottles.

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.

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

Downtown Chicago

Brock

$201 nightly

$239 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 hotel room with a large window, a bed, and a suitcase.

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

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

18. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Julian

$101 nightly

$120 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.

An indoor swimming pool with lounge chairs and a no diving sign.

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.

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Patricia

$188 nightly

$223 total

Nov 1 - Nov 2

Total with taxes and fees

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

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$145 nightly

$172 total

Nov 1 - Nov 2

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

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."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Staff was very helpful"

Central Loop Hotel

10/10 Excellent

"I liked the location and staff"

Hilton Chicago

10/10 Excellent

"Convenient location walk to anything you might need, restaurants, shopping, Room was so nice and comfortable"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"If I could give more than 5 stars I would. The staff was amazing and extremely accommodating and flexible. The rooms were gorgeous and the hotel was beautiful."

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."

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

6.8/10 (2,363 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 7 - Oct 8

Total with taxes and fees

6.2/10 (1,295 reviews)

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! (1,640 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$118 nightly

$139 total

Nov 1 - Nov 2

Total with taxes and fees

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 Chicago

6. Hilton Garden Inn Chicago Downtown South Loop

7. Homewood Suites by Hilton Chicago Downtown South Loop

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

9. Hilton Vacation Club Hotel Blake Chicago

10. Congress Plaza Hotel

11. SureStay Plus Hotel by Best Western Chicago Lombard

12. Hampton Inn Chicago-O'Hare International Airport

13. Travelodge by Wyndham Downtown Chicago

14. Le Méridien Essex Chicago

15. Hampton Inn Chicago West Loop Fulton Market Area

16. Hyatt House Chicago/West Loop-Fulton Market

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

18. Club Quarters Hotel, Central Loop, Chicago

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

20. Crowne Plaza Chicago West Loop by IHG

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 Royal Sonesta Chicago Downtown

Hotel Saint Clair- Magnificent Mile

Central Loop Hotel

Hilton Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Hampton Inn Chicago Downtown/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

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

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