Southwest Side B&B

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Our top choices for Southwest Side bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Lakeview

Ginny

RM315 total

includes taxes & fees

24 Nov - 25 Nov

A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

2. The Villa Toscana

Lakeview

John

RM438 total

includes taxes & fees

3 Nov - 4 Nov

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

3. The Sono Chicago

Near North Side

Tavarion

RM772 total

includes taxes & fees

9 Nov - 10 Nov

A bathroom with a glass-tiled wall, a sink, and a shower area.

4. Ray's Bucktown B&B

Bucktown

Lora

RM895 total

includes taxes & fees

3 Nov - 4 Nov

A grand foyer with a wooden staircase, a chandelier, and a large window.

5. Villa D' Citta

Lincoln Park

Hernando

RM981 total

includes taxes & fees

2 Dec - 3 Dec

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

6. Harvey House Bed & Breakfast

Oak Park

Monica

RM1,162 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

7. House 5863 - Chicago Bed and Breakfast

Edgewater

Malena

RM814 total

includes taxes & fees

8 Nov - 9 Nov

A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

West Town

Mary

RM1,198 total

includes taxes & fees

16 Nov - 17 Nov

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

9. The Publishing House B&B

Downtown Chicago

Nobue

RM1,446 total

includes taxes & fees

8 Nov - 9 Nov

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Top Southwest Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"The staff at the concierge were very knowledgeable and helpful day 1 until 4, On my second night, oct 29th, except for the lady staff who was in the lobby bar, she was not accommodating and just giving us a negative answer when we are asking if there if coffee is included in the drinks voucher, she did not even us told us that there was Keurig coffee maker an the right side corner, she is the only one that"

L7 Chicago by LOTTE

10/10 Excellent

"Best hotel sleep in years, which is wild given the central location in a busy city. In-room amenities like the steamer, robe, kettle and yoga mat really elevated my stay. No onsite food except that expensive restaurant downstairs, but there’s an amazing pub literally across the street that’s huge, reasonable and open late. Free coffee in lobby was nice too. Only drawback was the lack of a desk chair in the room. There was a lounger and a table but trying to work from it for more than a few hours was a little rough in my back. I’d definitely stay again."

Arlo Chicago

10/10 Excellent

"Arlo Chicago was perfect! If you are in a wheelchair, the ADA King room was fully accessible with a low sitting bed, walk-in shower, open sinks, and enough space to get around room. It was quiet with electric blinds making it easy to open/close. The location is within walking distance of just about anything, or a bus stop and train station right out front or a block down to access train. The famous Bean site was a 2 minute walk, the Riverwalk about 5 minutes, and so much more. The parking was so easy. You pull right at back door & unload, and the parking garage is literally at the end of that alley. That was my biggest concern being my first overnight stay in a wheelchair where I must transfer in/out my chair. There is a bar and restaurant inside the hotel, drinks (for a fee) already in the room, a refrigerator, alcohol, water, soda, coffee machine, toiletries, robes, etc. The view was awesome. Thank you for the amazing staff who were so kind & helpful...especially Terell who was more than accommodating in helping us register with parking garage online. The room was clean, common areas welcoming, and I will only stay at this location in the future. My only criticism is that the ADA room had a heavy door and was a sharp right angle to enter, which could potentially be an issue for an electric wheelchair user if they were traveling alone...but the staff would have helped. Be prepared financially, but our room was worth the rate & reasonable for all the amenities."

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