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

Go beyond your typical stay in Southwest Side

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

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

$145 nightly

$168 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 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

$107 nightly

$126 total

Oct 20 - Oct 21

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

A compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 19 - Oct 20

Total with taxes and fees

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

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

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.

4. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Nov 8 - Nov 9

Total with taxes and fees

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

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

5. Best Western Grant Park Hotel

Downtown Chicago

Colin

$107 nightly

$127 total

Nov 10 - Nov 11

Total with taxes and fees

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

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

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

6. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

$144 nightly

$171 total

Nov 10 - Nov 11

Total with taxes and fees

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

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

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

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

7. Le Méridien Essex Chicago

Downtown Chicago

Caitlin Vania

$157 nightly

$187 total

Nov 9 - Nov 10

Total with taxes and fees

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

A conference room with a long table, chairs, and a large screen.

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

A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

8. Hilton Chicago

Downtown Chicago

Anna

$194 nightly

$230 total

Nov 13 - Nov 14

Total with taxes and fees

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

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.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

9. Congress Plaza Hotel

Downtown Chicago

Ashya

$108 nightly

$129 total

Nov 11 - Nov 12

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 hotel room with two beds, a desk, a chair, a TV, and a window with a view.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

10. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

$124 nightly

$143 total

Oct 25 - Oct 26

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 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 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

Caleb

$97 nightly

$107 total

Oct 26 - Oct 27

Total with taxes and fees

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

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.

12. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

$172 nightly

$204 total

Nov 3 - Nov 4

Total with taxes and fees

A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.

A hotel room with a bed, desk, chair, two small tables, a sofa, and a large window with a city view.

A modern lobby with a central seating area, a reception desk, and elevators.

A spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.

13. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Donna

$158 nightly

$188 total

Nov 11 - Nov 12

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 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.

14. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$112 nightly

$133 total

Nov 11 - Nov 12

Total with taxes and fees

A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a staircase, and large windows providing natural light.

A modern restaurant with a mix of seating options including tables and sofas, a kitchen area, and large windows offering views of the outdoors.

A hotel room with a bed, a desk, a chair, a sofa, and a television.

A swimming pool with lounge chairs and a view of the outside.

15. Wingate by Wyndham Tinley Park

Tinley Park

Erica

$116 nightly

$131 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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.

16. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Christian

$121 nightly

$143 total

Nov 11 - Nov 12

Total with taxes and fees

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

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.

A modern lounge area with seating, a bar, and large windows offering views.

17. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

$195 nightly

$232 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 hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

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

18. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

$161 nightly

$191 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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 hotel lobby with a reception desk, seating area, and a view of the city.

19. Best Western River North Hotel

Downtown Chicago

Jordan

$118 nightly

$140 total

Nov 9 - Nov 10

Total with taxes and fees

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

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

A modern interior with a dining area, sofas, and artwork on the walls.

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

20. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Robert

$142 nightly

$168 total

Nov 2 - Nov 3

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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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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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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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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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

Congress Plaza Hotel

10/10 Excellent

"The location is spectacular! The lobby is beautiful with historic charm. Our room was updated and modern. I’d stay here again!"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"We had an early arrival, and first had only planned to store the luggage. Very friendly at reception had a nice surprise that rooms were already available - no extra costs. All staff was very attentive,"

L7 Chicago by LOTTE

8/10 Good

"We loved the window seats, and Nespresso machine, but we were disappointed that a microwave wasn’t included in the room. We did not try the restaurant on-site. Parking was valet and $69. Room was spacious and beds were comfortable. Room was a little noisy, with ambulance and traffic sounds."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Room is spacious, very clean hotel. I would recommend."

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 26 - Oct 27

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 25 - Oct 26

Total with taxes and fees

6.4/10 (1,313 reviews)

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$97 nightly

$107 total

Oct 26 - Oct 27

Total with taxes and fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$110 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,682 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$112 nightly

$133 total

Nov 11 - Nov 12

Total with taxes and fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

$124 nightly

$143 total

Oct 25 - Oct 26

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

Go beyond your typical stay in Southwest Side

Check prices for these dates

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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. Best Western Grant Park Hotel

6. Homewood Suites by Hilton Chicago Downtown South Loop

7. Le Méridien Essex Chicago

8. Hilton Chicago

9. Congress Plaza Hotel

10. Hampton Inn Chicago-O'Hare International Airport

11. SureStay Plus Hotel by Best Western Chicago Lombard

12. Hilton Vacation Club Hotel Blake Chicago

13. Holiday Inn & Suites Chicago - Downtown by IHG

14. Travelodge by Wyndham Downtown Chicago

15. Wingate by Wyndham Tinley Park

16. The Chicago Hotel Collection Ambassador Gold Coast

17. Hyatt House Chicago/West Loop-Fulton Market

18. Crowne Plaza Chicago West Loop by IHG

19. Best Western River North Hotel

20. Hotel Saint Clair- Magnificent Mile

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

S.S. Peter and Paul Church

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Congress Plaza Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

L7 Chicago by LOTTE

The Royal Sonesta Chicago Downtown

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