Top 10 Hotels in Southwest Side (from $64) 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 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.

A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Diane

$137 nightly

$159 total

Sep 7 - Sep 8

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 flat-screen TV mounted above a fireplace, flanked by two potted plants.

2. Carlton Inn Midway

Archer Heights

Rahul Pandit

$117 nightly

$137 total

Aug 31 - Sep 1

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

3. Rainbow Motel

Garfield Ridge

Noel

$77 nightly

$90 total

Aug 31 - Sep 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 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.

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

Downtown Chicago

Ashraf

$198 nightly

$236 total

Sep 7 - Sep 8

Total with taxes and fees

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

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

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.

5. Congress Plaza Hotel

Downtown Chicago

George

$116 nightly

$138 total

Sep 8 - Sep 9

Total with taxes and fees

A hotel entrance with a marquee and string lights above the entrance.

A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.

A hotel entrance with a marquee, American flag, and a person standing in front.

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

$181 nightly

$216 total

Sep 1 - Sep 2

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

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

7. Best Western Grant Park Hotel

Downtown Chicago

Diego

$143 nightly

$170 total

Sep 7 - Sep 8

Total with taxes and fees

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

A man in a suit sitting by a window with a vase of red flowers.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

8. River Hotel

Downtown Chicago

Patti

$140 nightly

$167 total

Sep 8 - Sep 9

Total with taxes and fees

A large, multi-story hotel with a prominent entrance and classical architectural details.

A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.

A spacious hotel lobby with a long reception desk, multiple seating areas, and a large fireplace.

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

9. Hilton Chicago

Downtown Chicago

Konner

$194 nightly

$230 total

Sep 7 - Sep 8

Total with taxes and fees

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

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.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

10. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Brittany

$117 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

A cozy room with a sofa, a dining table, and a window with a view of buildings.

A lobby with two brown leather chairs, a marble table, and a large potted plant.

A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

11. LIVN - West Loop Chicago

Downtown Chicago

Courtney

$128 nightly

$150 total

Aug 30 - Aug 31

Total with taxes and fees

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

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.

A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

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

12. The Wade

Downtown Chicago

Ayomikun Jedidiah

$149 nightly

$177 total

Aug 30 - Aug 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 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.

13. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dhannetta

$152 nightly

$181 total

Sep 7 - Sep 8

Total with taxes and fees

A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

A modern kitchen area with a long counter, various food items, and a coffee machine.

A modern room with a checkered floor, two round tables, two armchairs, and a large window with a view of the outside.

A hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.

14. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Karaline

$123 nightly

$146 total

Sep 7 - Sep 8

Total with taxes and fees

A hotel bathroom with a large mirror, a sink, and a vanity.

A bakery display with pastries and a coffee shop sign in the background.

A gym with various exercise equipment, including treadmills and weight machines.

A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.

15. Sports Illustrated Resorts Chicago

Downtown Chicago

CHRISTIE

$209 nightly

$249 total

Aug 31 - Sep 1

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 bed, a TV, a desk, and a chair.

A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.

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

16. Central Loop Hotel

Downtown Chicago

Yiyang

$137 nightly

$163 total

Aug 31 - Sep 1

Total with taxes and fees

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.

A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.

A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

17. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Jyothi Swaroop

$144 nightly

$171 total

Sep 7 - Sep 8

Total with taxes and fees

A grand staircase in a hotel lobby with marble walls, a patterned carpet, and seating areas with blue and brown upholstered chairs.

A tall building with a classic architectural style, featuring a central entrance with ornate details and large windows.

A grand hallway with ornate doors, a marble floor, and a chandelier.

A hotel room with a grey sofa, a bed with a wooden headboard, a wooden dresser, and a large window with curtains.

18. Club Quarters Hotel Wacker at Michigan, Chicago

Downtown Chicago

Daphnie

$117 nightly

$140 total

Sep 8 - Sep 9

Total with taxes and fees

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

19. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

susie

$161 nightly

$191 total

Sep 8 - Sep 9

Total with taxes and fees

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

A grilled pineapple on top of a stack of meat, served on a pan.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

20. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

$188 nightly

$224 total

Aug 30 - Aug 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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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 acclaimed theater 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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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 Wade

8/10 Good

"Conveniently located"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Gorgeous huge room with giant windows. Amazing fast staff, especially the valet/bellhops. Beautiful property, amazing location. Awesome pool."

Hyatt Regency Chicago

8/10 Good

"Muy bueno, vista espectacular, buen servicio"

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"The staff were super kind and helpful. The hotel qas in a great location. Would come back again!"

L7 Chicago by LOTTE

10/10 Excellent

"Amazing experience with the front desk Alex is great very helpful"

Hilton Chicago

10/10 Excellent

"I really enjoyed that they made the BTS ARMY guests feel welcomed"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Room was stylish and clean, comfy bed and nice bathroom. Great location right in the middle of Theater District/River North!"

River Hotel

10/10 Excellent

"Awesome place in a great location"

Palmer House a Hilton Hotel

10/10 Excellent

"Beautiful hotel with lots of personality and charm. Great staff, great location, lots of options for food easily available."

More cheap stays in Southwest Side

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$57 nightly

$64 total

Sep 13 - Sep 14

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$62 nightly

$69 total

Sep 8 - Sep 9

Total with taxes and fees

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

$83 nightly

$93 total

Sep 27 - Sep 28

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$115 nightly

$137 total

Aug 31 - Sep 1

Total with taxes and fees

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

$137 nightly

$159 total

Sep 7 - Sep 8

Total with taxes and fees

8.2/10 Very Good! (1,008 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$148 nightly

$176 total

Sep 7 - Sep 8

Total with taxes and fees

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia

Lodging

Find hotels in Southwest Side, IL from $64

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. Sable at Navy Pier Chicago, Curio Collection by Hilton

5. Congress Plaza Hotel

6. Hilton Vacation Club Hotel Blake Chicago

7. Best Western Grant Park Hotel

8. River Hotel

9. Hilton Chicago

10. The Chicago Hotel Collection Ambassador Gold Coast

11. LIVN - West Loop Chicago

12. The Wade

13. Hilton Garden Inn Chicago Downtown South Loop

14. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

15. Sports Illustrated Resorts Chicago

16. Central Loop Hotel

17. Courtyard by Marriott Chicago Magnificent Mile

18. Club Quarters Hotel Wacker at Michigan, Chicago

19. Hilton Chicago/Magnificent Mile Suites

20. Hyatt Centric The Loop Chicago

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

S.S. Peter and Paul Church

Union Stock Yard Gate

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Wade

InterContinental Chicago Magnificent Mile by IHG

Hyatt Regency Chicago

The Chicago Hotel Collection - Magnificent Mile

L7 Chicago by LOTTE

Hilton Chicago

The Allegro Royal Sonesta Hotel Chicago Loop

River Hotel

Palmer House a Hilton Hotel

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Quality Inn & Suites Orland Park - Chicago

Travelodge by Wyndham Downtown Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star-rating

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