Bed and Breakfast in Historic Route 66

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Featured B&B in Historic Route 66

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!"

includes taxes & fees

24 July - 25 July

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

"Was a great stay!"

includes taxes & fees

24 July - 25 July

Stunning lodge-style building with a charming front porch and stone pillars.

"This is a quaint bed and breakfast. Wonderfully decorated and breakfast was cooked to order. Highly recommend this B&B"

includes taxes & fees

28 July - 29 July

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 "

includes taxes & fees

3 Aug - 4 Aug

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! "

includes taxes & fees

24 July - 25 July

Enjoy the charming balcony with a metal railing and two wicker chairs.

"Great stay! "

includes taxes & fees

24 July - 25 July

Cozy retreat with a four-poster bed, nightstands, and a fireplace.

"I have always loved staying at the Walnut Street Inn. Comfortable rooms, great staff and yummy breakfast!"

includes taxes & fees

27 July - 28 July

Relax in the cabin's central hot tub, surrounded by views of the surrounding area.

"The team here was fantastic and the food was amazing! We highly recommend! "

includes taxes & fees

24 July - 25 July

Surrounded by lush greenery, this outdoor space features a stone column structure and a metal roof, with a pathway leading to a glass door entrance.

"It was what I need I loved the whole site of the property can't wait too come back "

includes taxes & fees

13 Aug - 14 Aug

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!"

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

"Excellent location. Beautiful property, extremely clean."

includes taxes & fees

4 Aug - 5 Aug

Charming single-story home with a front porch and a gravel driveway.

"Great spot! Very close to historic Route 66, and other attractions. Very clean, easy check-in, and love the fire pits/giant Jenga/hammocks on site."

includes taxes & fees

28 July - 29 July

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

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

includes taxes & fees

20 Aug - 21 Aug

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!"

includes taxes & fees

24 July - 25 July