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

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Southwest Side

Pet friendly

Apartment

Condo

Spa

Apart hotel

Hot tub

Pool

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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

Allen

$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 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.

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 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.

A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 5 - Oct 6

Total with taxes and fees

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

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

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 27 - Oct 28

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

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

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$172 nightly

$204 total

Nov 3 - Nov 4

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.

6. Hilton Chicago

Downtown Chicago

Alan

$190 nightly

$226 total

Oct 30 - Oct 31

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

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

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

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

Downtown Chicago

Shanequa

$258 nightly

$307 total

Oct 4 - Oct 5

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 hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

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.

8. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$85 nightly

$94 total

Oct 4 - Oct 5

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 cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

9. Congress Plaza Hotel

Downtown Chicago

Guadalupe

$113 nightly

$135 total

Nov 2 - Nov 3

Total with taxes and fees

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

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.

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

10. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

$190 nightly

$226 total

Oct 25 - Oct 26

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 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.

11. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$190 nightly

$225 total

Oct 25 - Oct 26

Total with taxes and fees

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

$116 nightly

$136 total

Nov 2 - Nov 3

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 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.

13. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$193 nightly

$229 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 restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

A modern living room with a sofa, chairs, 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.

14. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

$247 nightly

$294 total

Oct 31 - Nov 1

Total with taxes and fees

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

A modern lounge area with a sofa, chairs, and a large potted plant.

A spacious indoor area with seating arrangements, large windows, and indoor plants.

A modern lobby with a sofa, coffee table, and potted plants.

15. The Emily Hotel

Downtown Chicago

Leslie

$209 nightly

$248 total

Nov 1 - Nov 2

Total with taxes and fees

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

Catherine

$138 nightly

$164 total

Nov 1 - Nov 2

Total with taxes and fees

A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

A grand hall with a central aisle, ornate chandeliers, and rows of chairs.

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

17. Palmer House a Hilton Hotel

Downtown Chicago

Gabriella

$218 nightly

$256 total

Oct 31 - Nov 1

Total with taxes and fees

A modern kitchen with a marble island, fruit bowls, and a city view.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

18. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

$199 nightly

$237 total

Oct 31 - Nov 1

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 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.

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.

19. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$128 nightly

$152 total

Nov 2 - Nov 3

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 a seating area, a reception desk, and a large screen.

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$145 nightly

$172 total

Nov 1 - Nov 2

Total with taxes and fees

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate.

See properties

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.

See properties

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

L7 Chicago by LOTTE

10/10 Excellent

"Nice rooms, decor and well placed for city experiences"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"This was comfortable, well-located and cheaper than many of the other options during a busy week. The best amenity turned out to be the washer and drier since I was here for a cooking class and need to wash a chef's jacket every night."

Central Loop Hotel

10/10 Excellent

"Clean room great staff"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great location in the middle of et; amazing view of the river;"

Eurostars Magnificent Mile

8/10 Good

"Slight wear and tear on the furniture dates the place and I wish the rooms were brighter, but excellent location and great value. Loved the shower!"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Excellent location!"

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 (2,342 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 10 - Oct 11

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$93 nightly

$104 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

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$116 nightly

$136 total

Nov 2 - Nov 3

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

Explore a world of travel with Expedia

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. Hilton Chicago

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

8. SureStay Plus Hotel by Best Western Chicago Lombard

9. Congress Plaza Hotel

10. Homewood Suites by Hilton Chicago Downtown South Loop

11. Hilton Garden Inn Chicago Downtown South Loop

12. Travelodge by Wyndham Downtown Chicago

13. Hyatt House Chicago/West Loop-Fulton Market

14. Le Méridien Essex Chicago

15. The Emily Hotel

16. Hampton Inn & Suites Chicago Downtown

17. Palmer House a Hilton Hotel

18. Fairmont Chicago at Millennium Park

19. Hotel Saint Clair- 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

L7 Chicago by LOTTE

The Chicago Hotel Collection Ambassador Gold Coast

Hotel Saint Clair- Magnificent Mile

Central Loop Hotel

The Royal Sonesta Chicago Downtown

Eurostars Magnificent Mile

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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

Go further with the Expedia app