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 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 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.

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

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.

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

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

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

3. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Oct 15 - Oct 16

Total with taxes and fees

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

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

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

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

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

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

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

5. 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 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.

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

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$172 nightly

$204 total

Nov 3 - Nov 4

Total with taxes and fees

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.

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.

7. 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 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.

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

8. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

$190 nightly

$226 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 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.

A snack and beverage kiosk with various snacks and drinks.

9. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$93 nightly

$104 total

Oct 4 - Oct 5

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.

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

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 lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

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 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.

A restaurant with booths, tables, and a green wall in the background.

12. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$116 nightly

$136 total

Nov 2 - Nov 3

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

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

13. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

$247 nightly

$294 total

Oct 31 - Nov 1

Total with taxes and fees

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

A modern building with large glass windows and a covered walkway.

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

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

14. Palmer House a Hilton Hotel

Downtown Chicago

Gabriella

$218 nightly

$256 total

Oct 31 - Nov 1

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

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

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

15. Wingate by Wyndham Tinley Park

Tinley Park

Gregory

$105 nightly

$118 total

Nov 1 - Nov 2

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

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

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

16. The Emily Hotel

Downtown Chicago

Leslie

$209 nightly

$248 total

Nov 1 - Nov 2

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.

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

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

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

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.

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

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

18. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

$199 nightly

$237 total

Oct 31 - Nov 1

Total with taxes and fees

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

A bar with a brick archway, wooden bar counter, and stools.

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.

19. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Synova

$102 nightly

$122 total

Nov 1 - Nov 2

Total with taxes and fees

A bar area with a bar counter, multiple stools, a shelf with bottles, and a framed portrait on the wall.

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.

20. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Marta

$143 nightly

$170 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

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"The room was very spacious. The location of the hotel was great. The breakfast was delicious. We will definitely stay here again!"

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;"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Stayed for a couple of days with my wife, no real issues. Room was clean and well-maintained, bed was comfortable. We did not op for the vip package so we were room only. All our needs were met and we would come back!"

L7 Chicago by LOTTE

10/10 Excellent

"Great hotel right by the river, clean and spacious rooms"

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 (2,368 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 9 - Oct 10

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. Carlton Inn Midway

2. Rainbow Motel

3. Carleton of Oak Park

4. Hilton Chicago

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

6. Hilton Vacation Club Hotel Blake Chicago

7. Congress Plaza Hotel

8. Homewood Suites by Hilton Chicago Downtown South Loop

9. SureStay Plus Hotel by Best Western Chicago Lombard

10. Hyatt House Chicago/West Loop-Fulton Market

11. Hilton Garden Inn Chicago Downtown South Loop

12. Travelodge by Wyndham Downtown Chicago

13. Le Méridien Essex Chicago

14. Palmer House a Hilton Hotel

15. Wingate by Wyndham Tinley Park

16. The Emily Hotel

17. Hampton Inn Chicago-O'Hare International Airport

18. Fairmont Chicago at Millennium Park

19. Club Quarters Hotel, Central Loop, Chicago

20. The Chicago Hotel Collection Ambassador Gold Coast

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 Chicago Hotel Collection - Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Central Loop Hotel

The Royal Sonesta Chicago Downtown

The Chicago Hotel Collection Ambassador Gold Coast

L7 Chicago by LOTTE

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