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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured B&B in Historic Route 66

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

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (51)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is S$191
includes taxes & fees
16 Jul - 17 Jul
Dorothy's
The Villa Toscana
Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (583)
"Was a great stay!"
The price is S$158
includes taxes & fees
16 Jul - 17 Jul
The Villa Toscana
The Lodge at Grant's Trail
Stunning lodge-style building with a charming front porch and stone pillars.

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (434)
"This is a quaint bed and breakfast. Wonderfully decorated and breakfast was cooked to order. Highly recommend this B&B"
The price is S$197
includes taxes & fees
16 Jul - 17 Jul
The Lodge at Grant's Trail
House 5863 - Chicago Bed and Breakfast
Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (474)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is S$289
includes taxes & fees
21 Jul - 22 Jul
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (365)
"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! "
The price is S$283
includes taxes & fees
16 Jul - 17 Jul
Ray's Bucktown B&B
Red Garter Inn
Enjoy the charming balcony with a metal railing and two wicker chairs.

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (472)
"I was not expecting such a nice room and so I was very surprised at how nice this Inn is in the great location in the historic downtown. I will definitely stay here again!"
The price is S$202
includes taxes & fees
21 Jul - 22 Jul
Red Garter Inn
Walnut Street Inn
Cozy retreat with a four-poster bed, nightstands, and a fireplace.

Walnut Street Inn

3.5 star property
9.4 out of 10, Exceptional, (177)
"I have always loved staying at the Walnut Street Inn. Comfortable rooms, great staff and yummy breakfast!"
The price is S$209
includes taxes & fees
9 Aug - 10 Aug
Walnut Street Inn
Loba Luna Bed & Breakfast
Relax in the cabin's central hot tub, surrounded by views of the surrounding area.

Loba Luna Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (62)
"The team here was fantastic and the food was amazing! We highly recommend! "
The price is S$227
includes taxes & fees
16 Jul - 17 Jul
Loba Luna Bed & Breakfast
WangShi China Palace B&B
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.

WangShi China Palace B&B

3.5 star property
9.4 out of 10, Exceptional, (93)
"It was what I need I loved the whole site of the property can't wait too come back "
The price is S$240
includes taxes & fees
9 Aug - 10 Aug
WangShi China Palace B&B
Wicker Park Inn
Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (248)
"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!"
Wicker Park Inn
The Sono Chicago
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (463)
"Excellent location. Beautiful property, extremely clean."
The price is S$314
includes taxes & fees
23 Jul - 24 Jul
The Sono Chicago
Trapper's Rendezvous
Charming single-story home with a front porch and a gravel driveway.

Trapper's Rendezvous

4.0 star property
9.8 out of 10, Exceptional, (30)
"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."
The price is S$220
includes taxes & fees
17 Jul - 18 Jul
Trapper's Rendezvous
The Publishing House B&B
Staircase leads to an upper level with potted plants and decorative shelves.

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is S$264
includes taxes & fees
27 Jul - 28 Jul
The Publishing House B&B
Harvey House Bed & Breakfast
Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"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!"
The price is S$384
includes taxes & fees
16 Jul - 17 Jul
Harvey House Bed & Breakfast
Villa D' Citta
Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (103)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
The price is S$396
includes taxes & fees
16 Jul - 17 Jul
Villa D' Citta
Harwelden Mansion
Stately brick building with a central entrance and symmetrical facade, surrounded by a beautifully maintained garden.

Harwelden Mansion

3.5 star property
10.0 out of 10, Exceptional, (27)
"The Sycamore Suite was very comfortable and inviting. Lots of room. The patio was nice as well. Beautiful grounds. "
The price is S$916
includes taxes & fees
16 Jul - 17 Jul
Harwelden Mansion
Bobcat Inn Bed and Breakfast
Relax in a serene outdoor setting with a covered patio and peaceful pond.

Bobcat Inn Bed and Breakfast

3.0 star property
9.8 out of 10, Exceptional, (82)
"Location and the accomodation were lovely and the hosts were incredibly friendly and helpful."
Bobcat Inn Bed and Breakfast
Elden Trails Bed and Breakfast
Enjoy the serene surroundings from this outdoor deck, featuring a covered space and a comfortable seating area.

Elden Trails Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (115)
"Very pleasant stay. Situated well for the things we wanted to do in the area."
The price is S$252
includes taxes & fees
7 Aug - 8 Aug
Elden Trails Bed and Breakfast
Inn Of The Turquoise Bear
Guests can enjoy a serene natural setting from this charming balcony with a scalloped edge, surrounded by lush greenery and beautiful flowers.

Inn Of The Turquoise Bear

4.0 star property
9.8 out of 10, Exceptional, (67)
"This is a beautiful place, a quiet peaceful oasis in the city "
Inn Of The Turquoise Bear
Four Kachinas Bed & Breakfast Inn
Enjoy a casual dining experience on the patio with a round table, comfortable chairs, and a beautiful potted plant.

Four Kachinas Bed & Breakfast Inn

3.5 star property
9.8 out of 10, Exceptional, (111)
"Location was great and convenient. "
The price is S$329
includes taxes & fees
16 Jul - 17 Jul
Four Kachinas Bed & Breakfast 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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