Find a Bed and Breakfast in Far Southwest Side from CA $111

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Browse Select Far Southwest Side B&B

Relax in this stylish living area with a large sofa, glass coffee table, and patterned rug.

"Great little spot with all you need. Clean, cozy and a great breakfast!"

CA $179 total

includes taxes & fees

Jul 23 - Jul 24

Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

"Was a great stay!"

CA $190 total

includes taxes & fees

Jul 23 - Jul 24

Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "

CA $290 total

includes taxes & fees

Jul 23 - Jul 24

Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "

CA $286 total

includes taxes & fees

Jul 23 - Jul 24

Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"

CA $370 total

includes taxes & fees

Aug 6 - Aug 7

Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

"Excellent location. Beautiful property, extremely clean."

CA $336 total

includes taxes & fees

Jul 23 - Jul 24

Staircase leads to an upper level with potted plants and decorative shelves.

"What a lovely place to stay. This bnb was perect!"

CA $337 total

includes taxes & fees

Jul 24 - Jul 25

Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"

CA $412 total

includes taxes & fees

Jul 24 - Jul 25

Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"

CA $461 total

includes taxes & fees

Jul 29 - Jul 30

Kitchen features a gas range, double sink, and dishwasher.

"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"

CA $266 total

includes taxes & fees

Jul 22 - Jul 23

"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...

CA $289 total

includes taxes & fees

Jul 22 - Jul 23