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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Fabian

$162 nightly

$188 total

Sep 27 - Sep 28

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

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

2. Carlton Inn Midway

Archer Heights

Icaro

$119 nightly

$140 total

Sep 23 - Sep 24

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

$86 nightly

$100 total

Sep 23 - Sep 24

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 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.

4. Carleton of Oak Park

Oak Park

Suzanne

$133 nightly

$148 total

Sep 28 - Sep 29

Total with taxes and fees

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

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

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

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

5. The Wade

Downtown Chicago

Fernanda

$149 nightly

$177 total

Sep 27 - Sep 28

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.

6. Congress Plaza Hotel

Downtown Chicago

John

$188 nightly

$223 total

Sep 27 - Sep 28

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.

7. Hilton Chicago

Downtown Chicago

Alan

$236 nightly

$281 total

Oct 12 - Oct 13

Total with taxes and fees

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

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.

A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

8. LIVN - West Loop Chicago

Downtown Chicago

chidubem

$190 nightly

$223 total

Sep 27 - Sep 28

Total with taxes and fees

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

A modern bathroom with a dual sink vanity, a large mirror, and a toilet.

9. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Ann

$373 nightly

$444 total

Oct 15 - Oct 16

Total with taxes and fees

A modern interior with a bar area, seating, and decorative wooden panels.

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.

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.

10. Best Western Grant Park Hotel

Downtown Chicago

Paige

$188 nightly

$224 total

Sep 27 - Sep 28

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

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

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

Downtown Chicago

Shanequa

$316 nightly

$376 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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.

12. River Hotel

Downtown Chicago

Isabella

$179 nightly

$213 total

Sep 27 - Sep 28

Total with taxes and fees

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

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

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

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

13. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Michael T.

$206 nightly

$245 total

Sep 27 - Sep 28

Total with taxes and fees

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

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

A spacious lobby with a marble floor, a reception desk, and a glass partition.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

14. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

$270 nightly

$321 total

Oct 13 - Oct 14

Total with taxes and fees

A grand lobby with a central bar, high ceilings, and classical architecture.

A modern living room with a sofa set, ottoman, and armchairs.

A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.

15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Tomasz

$143 nightly

$170 total

Sep 27 - Sep 28

Total with taxes and fees

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

A restaurant with outdoor seating and a sign for 'PIZANO'S PIZZA & PASTA'.

A neatly arranged hotel room with a large bed, a nightstand, a lamp, and a window with a view of buildings.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a coffee maker. There is a blue sofa and a round coffee table with a striped pattern. A dining area with a table and chairs is visible in the background.

16. LIVN - Millennium Park Downtown Chicago

Downtown Chicago

Rebecca

$222 nightly

$261 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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

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

17. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

$220 nightly

$262 total

Sep 27 - Sep 28

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

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

18. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Jacqueline

$142 nightly

$169 total

Sep 27 - Sep 28

Total with taxes and fees

A multi-story hotel with a prominent sign reading "Crowne Plaza."

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

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.

19. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Victoria

$189 nightly

$224 total

Sep 27 - Sep 28

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

20. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Tremecka

$152 nightly

$179 total

Sep 27 - Sep 28

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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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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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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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 Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Staff were very polite. Room very spacious. Would definitely stay there again. Thank you for the distilled water."

Hyatt Regency Chicago

10/10 Excellent

"Great place"

L7 Chicago by LOTTE

10/10 Excellent

"Excelent location, Good service and Great Restaurant."

River Hotel

8/10 Good

"N"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"My 4 y/o son loved the hotel pool. The location was nice as it was close to many attractions and a short walk to Whole Foods. Chief complaint: Car/motorcycle noise was bad. I’m a good sleeper, but the revving sounds kept me up."

Eurostars Magnificent Mile

10/10 Excellent

"."

Hilton Chicago

10/10 Excellent

"Rooms are large and very clean. Has a refrigerator, but no microwave."

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"amazing and friendly staff"

More cheap stays in Southwest Side

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$57 nightly

$64 total

Oct 7 - Oct 8

Total with taxes and fees

7.8/10 Good! (1,455 reviews)

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

$62 nightly

$70 total

Oct 4 - Oct 5

Total with taxes and fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

$118 nightly

$139 total

Oct 13 - Oct 14

Total with taxes and fees

8/10 Very Good! (2,123 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$152 nightly

$179 total

Sep 27 - Sep 28

Total with taxes and fees

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL

$190 nightly

$226 total

Sep 27 - Sep 28

Total with taxes and fees

8.4/10 Very Good! (1,347 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$195 nightly

$231 total

Sep 27 - Sep 28

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 $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. Carleton of Oak Park

5. The Wade

6. Congress Plaza Hotel

7. Hilton Chicago

8. LIVN - West Loop Chicago

9. Hilton Vacation Club Hotel Blake Chicago

10. Best Western Grant Park Hotel

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

12. River Hotel

13. The Chicago Hotel Collection Ambassador Gold Coast

14. Hotel Riu Plaza Chicago

15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

16. LIVN - Millennium Park Downtown Chicago

17. Hyatt Centric The Loop Chicago

18. Club Quarters Hotel, Central Loop, Chicago

19. Crowne Plaza Chicago West Loop by IHG

20. Travelodge by Wyndham Downtown Chicago

Stay near popular Southwest Side attractions

Marquette Park

S.S. Peter and Paul Church

Balzekas Museum of Lithuanian Culture

Union Stock Yard Gate

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

Hyatt Regency Chicago

L7 Chicago by LOTTE

River Hotel

InterContinental Chicago Magnificent Mile by IHG

Eurostars Magnificent Mile

Hilton Chicago

Holiday Inn Chicago – Midway Airport S by IHG

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Motel 6 Elk Grove Village, IL - O'Hare

Sleep Inn Midway Airport Bedford Park

Travelodge by Wyndham Downtown Chicago

Holiday Inn Express Chicago - Magnificent Mile by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star-rating

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