Top 10 Hotels in Southwest Side (from $71) 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 lobby with a vending machine, a statue, and an exit sign.

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

Paulina

$149 nightly

$173 total

Oct 25 - Oct 26

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

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 modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

2. Carlton Inn Midway

Archer Heights

Icaro

$119 nightly

$140 total

Oct 7 - Oct 8

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 compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

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

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 7 - Oct 8

Total with taxes and fees

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

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.

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

4. Carleton of Oak Park

Oak Park

Brad

$114 nightly

$127 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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

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.

6. Hilton Chicago

Downtown Chicago

Anna

$193 nightly

$227 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 waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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

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

Nov 1 - Nov 2

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 spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

8. Congress Plaza Hotel

Downtown Chicago

Katimah

$107 nightly

$127 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

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.

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$112 nightly

$131 total

Nov 2 - Nov 3

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 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 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

Shelby Ryann

$161 nightly

$192 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 snack and beverage kiosk with various snacks and drinks.

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 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.

11. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$89 nightly

$99 total

Oct 7 - Oct 8

Total with taxes and fees

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

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

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

12. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

$182 nightly

$216 total

Oct 25 - Oct 26

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 modern interior with a dining area, sofas, and artwork on the walls.

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.

13. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$128 nightly

$152 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$184 nightly

$219 total

Oct 25 - Oct 26

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 gym with various exercise equipment, large windows, and a city view.

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

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.

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

16. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

$143 nightly

$167 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 modern lounge area with a sofa, chairs, and a large potted plant.

A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.

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

17. The Emily Hotel

Downtown Chicago

Leslie

$204 nightly

$243 total

Nov 1 - Nov 2

Total with taxes and fees

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

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

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

18. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

$195 nightly

$232 total

Nov 1 - Nov 2

Total with taxes and fees

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

A hotel reception area with a black reception desk, a concierge service sign, and a tiled floor.

A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.

An indoor swimming pool with lounge chairs and a no diving sign.

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Patricia

$184 nightly

$219 total

Nov 1 - Nov 2

Total with taxes and fees

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 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.

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

20. Hotel 505 River North

Downtown Chicago

Giana

$256 nightly

$304 total

Nov 2 - Nov 3

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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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."

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"

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

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 13 - Oct 14

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$89 nightly

$99 total

Oct 7 - Oct 8

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

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

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$112 nightly

$131 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (2,887 reviews)

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

9.4/10 Exceptional! (2,396 reviews)

Hotels in Southwest Side with star-rating

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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. Congress Plaza Hotel

9. Travelodge by Wyndham Downtown Chicago

10. Best Western Grant Park Hotel

11. SureStay Plus Hotel by Best Western Chicago Lombard

12. Homewood Suites by Hilton Chicago Downtown South Loop

13. Hotel Saint Clair- Magnificent Mile

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hyatt House Chicago/West Loop-Fulton Market

16. Hampton Inn & Suites Chicago Downtown

17. The Emily Hotel

18. Hyatt Place Chicago/Downtown - The Loop

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

20. Hotel 505 River North

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

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection - Magnificent Mile

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

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