Search Historic Route 66 Bed & Breakfast

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured B&B in Historic Route 66

Our top choices for Historic Route 66 bed & breakfast

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (66)
"Very friendly and helpful staff. Rooms and bathrooms are very clean. I enjoyed my stay., it was cozy and comfortable. I would definitely stay at Dorothys again if I am back in the area.. I would also recommend it to friends meeting to stay near Wrigley or downtown."
The price is AU$146
includes taxes & fees
3 Sept - 4 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (592)
"Was a great stay!"
The price is AU$155
includes taxes & fees
1 Sept - 2 Sept
The Villa Toscana
The Lodge at Grant's Trail
Miscellaneous

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (444)
"Breakfasts was amazing "
The price is AU$240
includes taxes & fees
31 Aug - 1 Sept
The Lodge at Grant's Trail
Walnut Street Inn
Suite, 1 Queen Bed

Walnut Street Inn

3.5 star property
9.4 out of 10, Exceptional, (184)
"This place was cozy , welcoming, and beautiful "
The price is AU$196
includes taxes & fees
9 Sept - 10 Sept
Walnut Street Inn
Red Garter Inn
Classic Room, 2 Queen Beds | City view

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (479)
"very beautiful place to stay"
The price is AU$242
includes taxes & fees
2 Sept - 3 Sept
Red Garter Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (370)
"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 AU$319
includes taxes & fees
1 Sept - 2 Sept
Ray's Bucktown B&B
The Publishing House B&B
Staircase

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 AU$369
includes taxes & fees
21 Sept - 22 Sept
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (479)
"Everything was taken care of! A wonderful stay. "
The price is AU$302
includes taxes & fees
1 Sept - 2 Sept
House 5863 - Chicago Bed and Breakfast
The Mansion at Elfindale
Porch

The Mansion at Elfindale

3.5 star property
9.4 out of 10, Exceptional, (220)
"Very unique stay"
The price is AU$183
includes taxes & fees
10 Sept - 11 Sept
The Mansion at Elfindale
Loba Luna Bed & Breakfast
Indoor spa tub

Loba Luna Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (68)
"The staff was fantastic and so sweet. The property is beautiful."
The price is AU$271
includes taxes & fees
30 Aug - 31 Aug
Loba Luna Bed & Breakfast
Trapper's Rendezvous
Front of property

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 AU$256
includes taxes & fees
1 Sept - 2 Sept
Trapper's Rendezvous
Benton Park Inn
Hallway

Benton Park Inn

3.5 star property
9.6 out of 10, Exceptional, (298)
"Very inviting. Spacious room. Excellent breakfast. "
The price is AU$239
includes taxes & fees
22 Sept - 23 Sept
Benton Park Inn
Casa Culinaria The Gourmet Inn
Terrace/patio

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (253)
"Quaint, quiet and inviting. "
The price is AU$351
includes taxes & fees
1 Sept - 2 Sept
Casa Culinaria The Gourmet Inn
WangShi China Palace B&B
Property entrance

WangShi China Palace B&B

3.5 star property
9.2 out of 10, Wonderful, (97)
"Excellent"
The price is AU$406
includes taxes & fees
30 Aug - 31 Aug
WangShi China Palace B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (470)
"Loved the shared kitchen access! "
The price is AU$315
includes taxes & fees
3 Sept - 4 Sept
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AU$459
includes taxes & fees
1 Sept - 2 Sept
Harvey House Bed & Breakfast
Bottger Mansion of Old Town
Outdoor dining

Bottger Mansion of Old Town

3.5 star property
9.6 out of 10, Exceptional, (138)
"Wonderful experience, wonderful hosts. "
The price is AU$353
includes taxes & fees
8 Sept - 9 Sept
Bottger Mansion of Old Town
Bobcat Inn Bed and Breakfast
Courtyard view

Bobcat Inn Bed and Breakfast

3.0 star property
9.6 out of 10, Exceptional, (84)
"Location and the accomodation were lovely and the hosts were incredibly friendly and helpful."
Bobcat Inn Bed and Breakfast
Harwelden Mansion
Front of property

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 AU$1,095
includes taxes & fees
30 Aug - 31 Aug
Harwelden Mansion
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (106)
"Would stay again anytime!!"
The price is AU$536
includes taxes & fees
29 Sept - 30 Sept
Villa D' Citta
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Historic Route 66 Hotel Reviews

Find out more about Historic Route 66

Find out more about Historic Route 66

Historic Route 66 B&B information

Number of reviews
1,218
Accommodation
26 B&B
Lowest Price
AU$146
Highest Price
AU$1,095

Explore a world of travel with Expedia

Explore a world of travel with Expedia