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Check prices for these dates

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun
In one month
19 Jun - 21 Jun
In two months
17 Jul - 19 Jul

Our top choices for Historic Route 66 bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (514 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is HK$1,019
HK$1,196 total
includes taxes & fees
26 May - 27 May
The Sono Chicago
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (205 reviews)
"Super nice staff and clean rooms. Really neat and unique place to stay. Very relaxing"
United States
Matthew
The price is HK$2,302
HK$2,598 total
includes taxes & fees
11 Jun - 12 Jun
The Publishing House B&B
Hallway

Benton Park Inn

Benton Park Inn
3.5 star property
Benton Park
9.6 out of 10, Exceptional, (329 reviews)
"Great stay"
United States
Conor
The price is HK$1,167
HK$1,365 total
includes taxes & fees
26 May - 27 May
Benton Park Inn
Miscellaneous

The Lodge at Grant's Trail

The Lodge at Grant's Trail
3.5 star property
St. Louis
9.6 out of 10, Exceptional, (497 reviews)
"This was a perfect property for us. The staff were so friendly and welcoming. We will definitely stay there again. "
United States
Jean
The price is HK$1,167
HK$1,342 total
includes taxes & fees
25 May - 26 May
The Lodge at Grant's Trail
Lobby

Vrooman Mansion B&B

Vrooman Mansion B&B
2.5 star property
Bloomington
9.4 out of 10, Exceptional, (285 reviews)
"Amazing every visit"
United States
Danielle
The price is HK$1,856
HK$2,078 total
includes taxes & fees
25 May - 26 May
Vrooman Mansion B&B
Exterior detail

Bluebird Place

Bluebird Place
3.0 star property
Elk City
9.8 out of 10, Exceptional, (7 reviews)
"The room was nice and the bed was great! "
United States
Tom
The price is HK$1,285
HK$1,469 total
includes taxes & fees
25 May - 26 May
Bluebird Place
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (130 reviews)
"Absolutely perfect stay in Chicago. Everything we needed was there, breakfast was over the top amazing. I LOVE the area and the pizza spot downstairs, this place includes other perks also like BOGO well drink downstairs. Big Gay Sal’s pizza also does room service. I have never felt so at home away from home. 10/10 recommend, HIGHLY recommend"
United States
Jennifer
The price is HK$392
HK$734 total
includes taxes & fees
26 May - 27 May
Dorothy's
Front of property

Red Garter Inn

Red Garter Inn
3.0 star property
Downtown Williams
9.6 out of 10, Exceptional, (536 reviews)
"Great place loved it!"
United States
Wendy
The price is HK$846
HK$998 total
includes taxes & fees
31 May - 1 Jun
Red Garter Inn
Terrace/patio

Elden Trails Bed and Breakfast

Elden Trails Bed and Breakfast
3.0 star property
Flagstaff
9.2 out of 10, Wonderful, (120 reviews)
"Lovely cozy place to stay. Hosts were so kind and welcoming. The breakfast was incredible. Will definitely stay again!"
United States
Julia
The price is HK$1,387
HK$1,542 total
includes taxes & fees
27 May - 28 May
Elden Trails Bed and Breakfast
Gazebo

Red Horse Bed and Breakfast

Red Horse Bed and Breakfast
3.5 star property
Albuquerque
10.0 out of 10, Exceptional, (253 reviews)
"The breakfast was lovely and plentiful. The room was large and very comfortable. The staff were superb and tried to cater to all our needs."
United States
Linda
The price is HK$1,629
HK$1,730 total
includes taxes & fees
27 May - 28 May
Red Horse Bed and Breakfast
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (399 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is HK$1,193
HK$1,347 total
includes taxes & fees
25 May - 26 May
Ray's Bucktown B&B
Property entrance

Two Hearts Inn

Two Hearts Inn
4.0 star property
Edmond
9.2 out of 10, Wonderful, (329 reviews)
"Great place to stay! The room was great and the food was delicious!"
United States
Christopher
The price is HK$1,403
HK$1,602 total
includes taxes & fees
25 May - 26 May
Two Hearts Inn
Exterior

Santuario Grande

Santuario Grande
3.0 star property
Los Ranchos de Albuquerque
10.0 out of 10, Exceptional, (7 reviews)
"Amazing stay! Very memorable and relaxing. We will be back!"
United States
Tonie
The price is HK$2,071
HK$2,525 total
includes taxes & fees
13 Jun - 14 Jun
Santuario Grande
In-room safe, individually decorated, individually furnished

Trapper's Rendezvous

Trapper's Rendezvous
4.0 star property
Williams
9.6 out of 10, Exceptional, (43 reviews)
"Really enjoyed our stay will definitely book again if we're in the area"
United States
April
The price is HK$1,141
HK$1,345 total
includes taxes & fees
25 May - 26 May
Trapper's Rendezvous
Porch

Walnut Street Inn

Walnut Street Inn
3.5 star property
Downtown Springfield
9.4 out of 10, Exceptional, (223 reviews)
"This is the only place I’ll ever stay when visiting Springfield! Amazing historic rooms! Amazing helpful & friendly staff! Amazing five star breakfast! Perfect location! I would recommend the Walnut Street Inn to everyone! Thank you for yet another wonderful stay!"
United States
Ann
The price is HK$1,086
HK$1,233 total
includes taxes & fees
4 Jun - 5 Jun
Walnut Street Inn
Living area

Duets Bed & Breakfast

Duets Bed & Breakfast
3.5 star property
Pearl District
10.0 out of 10, Exceptional, (11 reviews)
"They were so friendly, place was spotless! loved the décor and hospitality. will definitely come back and refer others"
United States
Hugh
The price is HK$2,351
HK$2,551 total
includes taxes & fees
25 May - 26 May
Duets Bed & Breakfast
Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (642 reviews)
"Great location, beautiful charming spot in Chicago that is quiet but somehow in the middle of a big social scene"
United States
Joseph J
The price is HK$458
HK$851 total
includes taxes & fees
25 May - 26 May
The Villa Toscana
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is HK$2,053
HK$2,278 total
includes taxes & fees
4 Jun - 5 Jun
Harvey House Bed & Breakfast
Property entrance

WangShi China Palace B&B

WangShi China Palace B&B
3.5 star property
Oklahoma City
9.4 out of 10, Exceptional, (117 reviews)
"Lovely place, very striking aesthetics when you first arrive and walk in. The staff are incredibly friendly and accommodating, everything was great, I would definitely return!"
United States
Jacob Patrick
The price is HK$1,763
HK$2,078 total
includes taxes & fees
23 Jun - 24 Jun
WangShi China Palace B&B
Exterior

The Judge's Chambers

The Judge's Chambers
3.0 star property
Guthrie
10.0 out of 10, Exceptional, (9 reviews)
"Very historic and interesting property, well adapted with modern amenities while keeping its natural & historic heritage. Robin and her sweet Aunt were more than accommodating and welcoming. Definitely recommend visiting, we’ll be back soon we can explore more of the town."
United States
Stewart
The price is HK$1,575
HK$1,827 total
includes taxes & fees
25 May - 26 May
The Judge's Chambers
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly and helpful. "
Jocelyn 3-night trip
Posted 6 hours ago
Hotel Riu Plaza Chicago

Find out more about Historic Route 66

Historic Route 66 B&B information

Number of reviews
4,516
Accommodation
17 B&B
Lowest Price
HK$734
Highest Price
HK$2,598

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