𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Southwest Side from S$91 (2026) - Fully Refundable Options

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

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

S$209

includes taxes & fees

2 Nov - 3 Nov

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

2. Carlton Inn Midway

Archer Heights

Icaro

S$157

includes taxes & fees

15 Oct - 16 Oct

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

3. Rainbow Motel

Garfield Ridge

Jerry

S$126

includes taxes & fees

8 Oct - 9 Oct

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

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

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

S$261

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

5. Carleton of Oak Park

Oak Park

Brad

S$174

includes taxes & fees

27 Oct - 28 Oct

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 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.

6. Hilton Chicago

Downtown Chicago

Anna

S$289

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

Shelby Ryann

S$245

includes taxes & fees

25 Oct - 26 Oct

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

8. Congress Plaza Hotel

Downtown Chicago

Katimah

S$178

includes taxes & fees

4 Nov - 5 Nov

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

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.

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

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

S$172

includes taxes & fees

3 Nov - 4 Nov

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

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.

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.

10. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

S$139

includes taxes & fees

7 Oct - 8 Oct

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.

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

A modern restaurant interior with a long counter, booths, and tables.

11. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

S$276

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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.

12. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

S$171

includes taxes & fees

4 Nov - 5 Nov

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

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.

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

S$379

includes taxes & fees

31 Oct - 1 Nov

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

A modern hotel with a corner location, large windows, and a green awning.

14. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

S$228

includes taxes & fees

2 Nov - 3 Nov

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

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

Downtown Chicago

Shanequa

S$392

includes taxes & fees

1 Nov - 2 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

16. Hotel 505 River North

Downtown Chicago

Giana

S$389

includes taxes & fees

5 Nov - 6 Nov

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

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise 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.

17. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

S$283

includes taxes & fees

25 Oct - 26 Oct

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

A spacious lobby with a seating area, a reception desk, and a large screen.

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".

18. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Tommy

S$236

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

19. Palmer House a Hilton Hotel

Downtown Chicago

Sydney

S$327

includes taxes & fees

31 Oct - 1 Nov

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

20. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

S$328

includes taxes & fees

31 Oct - 1 Nov

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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 galleries.

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Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit 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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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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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

River Hotel

10/10 Excellent

"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"very helpful staff, large rest areas for waiting, good price, convenient location. A nice no-frills restaurant and bar onsite. Best choice for an Unpretentious visit stay."

Congress Plaza Hotel

8/10 Good

"Old hotel! Front desk wasn’t helpful l, ask for several things and they never showed up. No A.C., coffee pot broken, ran out of toilet paper and towels. No ice in machine, vending machine served hot beverages. Maintenance men were very nice, Christian at the bar was excellent! I’ll never stay there again."

The Wade

10/10 Excellent

"Real nice room facing the lake, comfy bed, nice decor, rain shower head, I prefer reg shower head, no Biggy ....one more thing, no coffee maker in the room but fresh coffee in the lobby."

Hyatt Regency Chicago

10/10 Excellent

"Beautiful hotel in a great location!"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Fantastic hotel! Really nice, clean, staff was incredibly friendly. We got the Fairmont gold room edition and it was totally worth it having food and drinks available during the day. We ate breakfast there each morning and it was great! Would definitely stay here again Next time we come to visit."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great location, good sized rooms, comfortable beds"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Midland hotel was clean and tidy, and the staff were accommodating, friendly, and helpful throughout our stay. We had a pleasant experience and would definitely return in the future!"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

S$91

21 Oct - 22 Oct

includes taxes & fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

S$116

12 Oct - 13 Oct

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

S$139

7 Oct - 8 Oct

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

S$172

3 Nov - 4 Nov

includes taxes & fees

7.8/10 Good! (2,887 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

S$197

25 Oct - 26 Oct

includes taxes & fees

9.4/10 Exceptional! (2,396 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

S$256

2 Nov - 3 Nov

includes taxes & fees

8/10 Very good! (1,658 reviews)

Southwest Side Hotels from S$91

Change your mind

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. Hilton Vacation Club Hotel Blake Chicago

5. Carleton of Oak Park

6. Hilton Chicago

7. Best Western Grant Park Hotel

8. Congress Plaza Hotel

9. Travelodge by Wyndham Downtown Chicago

10. SureStay Plus Hotel by Best Western Chicago Lombard

11. Homewood Suites by Hilton Chicago Downtown South Loop

12. Hotel Saint Clair- Magnificent Mile

13. Hyatt House Chicago/West Loop-Fulton Market

14. Hampton Inn & Suites Chicago Downtown

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

16. Hotel 505 River North

17. Hilton Garden Inn Chicago Downtown South Loop

18. Crowne Plaza Chicago West Loop by IHG

19. Palmer House a Hilton Hotel

20. Fairmont Chicago at Millennium Park

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

River Hotel

Club Quarters Hotel, Central Loop, Chicago

Congress Plaza Hotel

The Wade

Hyatt Regency Chicago

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection - Magnificent Mile

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star rating

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