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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 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, (64)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is AU$174
includes taxes & fees
7 Sept - 8 Sept
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (591)
"Was a great stay!"
The price is AU$218
includes taxes & fees
25 Aug - 26 Aug
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$238
includes taxes & fees
28 Aug - 29 Aug
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$197
includes taxes & fees
25 Aug - 26 Aug
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$257
includes taxes & fees
5 Sept - 6 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$315
includes taxes & fees
26 Aug - 27 Aug
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$350
includes taxes & fees
7 Sept - 8 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$304
includes taxes & fees
24 Aug - 25 Aug
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$184
includes taxes & fees
9 Sept - 10 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$273
includes taxes & fees
3 Sept - 4 Sept
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$264
includes taxes & fees
24 Aug - 25 Aug
Trapper's Rendezvous
Casa Culinaria The Gourmet Inn
Terrace/patio

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (252)
"We loved the property. It is a unique boutique establishment that is clearly decorated and maintained with care (including all of the little touches in both the rooms and in the gardens). We just wished that management were more hospitable. They can come across, intentionally or not, as a little brusque, if not rude. Without that, five stars for sure."
The price is AU$318
includes taxes & fees
24 Aug - 25 Aug
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$409
includes taxes & fees
31 Aug - 1 Sept
WangShi China Palace B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (468)
"Loved the shared kitchen access! "
The price is AU$282
includes taxes & fees
26 Aug - 27 Aug
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$462
includes taxes & fees
25 Aug - 26 Aug
Harvey House Bed & Breakfast
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
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is AU$518
includes taxes & fees
25 Aug - 26 Aug
Villa D' Citta
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$1,102
includes taxes & fees
5 Sept - 6 Sept
Harwelden Mansion
El Farolito Bed & Breakfast Inn
Front of property

El Farolito Bed & Breakfast Inn

3.5 star property
9.8 out of 10, Exceptional, (87)
"Loved the decor in our room. Breakfast was very good and the staff was very attentive and friendly."
The price is AU$438
includes taxes & fees
24 Aug - 25 Aug
El Farolito Bed & Breakfast Inn
Inn Of The Turquoise Bear
View from room

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
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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Top Historic Route 66 Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"It was great!"
Dewey Grant 3-night trip
Posted 6 hours ago
Hilton Chicago/Magnificent Mile Suites