Guest Houses in Southwest Side
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An airport with multiple runways, parked airplanes, and a large terminal building.

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your current months are November, 2026 and December, 2026.

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Our top choices for Southwest Side guest houses

A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.

A neatly made bed with a headboard, two bedside tables with lamps, and a wall-mounted artwork above the bed.

A room with a wooden herringbone ceiling, a wall clock, and shelves with various decorative items and books.

A modern kitchen with white cabinets, stainless steel appliances, and patterned wallpaper.

1. Villa Dubois Guest House

Villa Dubois Guest House

2.0 star property

Bronzeville

8.4 out of 10, Very good, (131 reviews)

8.4/10

Very good

(131 reviews)

"Our stay was great! The staff answered all of my questions promptly, it was easy to find and not having to pay for parking was a nice bonus."

Allie

The price is ￥14,379

￥14,379

￥16,879 total

includes taxes & fees

Dec 3 - Dec 4

Villa Dubois Guest House

A modern living room with a dark blue sofa, a glass coffee table, and a wooden log wall.

A bedroom with a large bed, a headboard, a wall-mounted artwork, and a window with curtains.

A modern living room with a fireplace, two armchairs, a sofa, and a large plant.

A modern kitchen with dark cabinetry, a stainless steel stove, and a glass-fronted upper cabinet.

2. Mccormick Place Guest House

Mccormick Place Guest House

3.0 star property

Bronzeville

8.6 out of 10, Excellent, (80 reviews)

8.6/10

Excellent

(80 reviews)

"Great parking and big living room."

Jasmine

The price is ￥15,143

￥15,143

￥17,776 total

includes taxes & fees

Dec 3 - Dec 4

Mccormick Place Guest House

A corner building with a black door, numbered 3305, and a black iron fence in front.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

A bedroom with a bed, bedside table, and a mirror on the wall.

3. Chicago Avenue Inn

Chicago Avenue Inn

2.0 star property

Humboldt Park

6.8 out of 10, (134 reviews)

6.8/10

(134 reviews)

"Clean place with a decent location."

Evelyn

The price is ￥7,929

￥7,929

￥18,208 total

includes taxes & fees

Nov 16 - Nov 17

Chicago Avenue Inn

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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.

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Search Guest Houses in Southwest Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Side guest houses

1. Villa Dubois Guest House

2. Mccormick Place Guest House

3. Chicago Avenue Inn

Learn more about Southwest Side

Explore a world of travel with Expedia