Find a Bed and Breakfast in Historic Route 66 from CA $96

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Historic Route 66 B&B

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (63)
"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 CA $96
CA $161 total
includes taxes & fees
Sep 7 - Sep 8
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (590)
"Was a great stay!"
The price is CA $120
CA $196 total
includes taxes & fees
Sep 8 - Sep 9
The Villa Toscana
The Lodge at Grant's Trail
Exterior

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (442)
"Breakfasts was amazing "
The price is CA $185
CA $213 total
includes taxes & fees
Aug 20 - Aug 21
The Lodge at Grant's Trail
Red Garter Inn
Classic Room, 2 Queen Beds | City view

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (478)
"very beautiful place to stay"
The price is CA $195
CA $230 total
includes taxes & fees
Aug 26 - Aug 27
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, (369)
"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 CA $239
CA $270 total
includes taxes & fees
Aug 14 - Aug 15
Ray's Bucktown 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 CA $188
CA $299 total
includes taxes & fees
Aug 25 - Aug 26
House 5863 - Chicago Bed and Breakfast
Casa Culinaria The Gourmet Inn
Terrace/patio

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (251)
"So well run. Grounds are amazing with so many edible plants used by the chef when preparing her delicious gourmet brunch. Highly recommend if looking for a complete experience in a boutique hotel combining excellent spacious rooms, each with pieces of the owners history, a wonderful gourmet brunch, beautiful grounds, and only 10 minutes from the Plaza. We will be back!"
The price is CA $260
CA $300 total
includes taxes & fees
Aug 26 - Aug 27
Casa Culinaria The Gourmet Inn
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 CA $155
CA $176 total
includes taxes & fees
Aug 19 - Aug 20
Walnut Street Inn
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 CA $201
CA $237 total
includes taxes & fees
Aug 17 - Aug 18
Trapper's Rendezvous
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 CA $267
CA $302 total
includes taxes & fees
Sep 2 - Sep 3
The Publishing House B&B
Loba Luna Bed & Breakfast
Indoor spa tub

Loba Luna Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (65)
"The staff was fantastic and so sweet. The property is beautiful."
The price is CA $230
CA $244 total
includes taxes & fees
Aug 27 - Aug 28
Loba Luna Bed & Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is CA $361
CA $413 total
includes taxes & fees
Aug 14 - Aug 15
Harvey House Bed & Breakfast
WangShi China Palace B&B
Property entrance

WangShi China Palace B&B

3.5 star property
9.2 out of 10, Wonderful, (95)
"It was what I need I loved the whole site of the property can't wait too come back "
The price is CA $310
CA $365 total
includes taxes & fees
Aug 17 - Aug 18
WangShi China Palace B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (466)
"Loved the shared kitchen access! "
The price is CA $248
CA $291 total
includes taxes & fees
Aug 18 - Aug 19
The Sono Chicago
Bobcat Inn Bed and Breakfast
Courtyard view

Bobcat Inn Bed and Breakfast

3.0 star property
9.6 out of 10, Exceptional, (83)
"Excellent staff property b+ area away from all attractions "
Bobcat Inn Bed and Breakfast
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 CA $340
CA $391 total
includes taxes & fees
Sep 1 - Sep 2
El Farolito Bed & Breakfast Inn
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 CA $867
CA $985 total
includes taxes & fees
Aug 26 - Aug 27
Harwelden Mansion
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 CA $394
CA $463 total
includes taxes & fees
Aug 17 - Aug 18
Villa D' Citta
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 "
The price is CA $358
CA $413 total
includes taxes & fees
Aug 20 - Aug 21
Inn Of The Turquoise Bear
Central West End B&B
(Lil Dynasty) No Private Bathroom

Central West End B&B

3.5 star property
7.8 out of 10, Good, (53)
"We enjoyed our stay in this historic house. The breakfast was good, though not elaborate or fancy. The owner and the staff were both friendly."
The price is CA $215
CA $272 total
includes taxes & fees
Aug 14 - Aug 15
Central West End B&B
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Super fun place to stay in the heart of Chicago. The lights and shades are controlled by an IPad. One of the many features is the ability to change the color and intensity of the lights. There are also built in "mood" sound tracks to play to help you unwind, relax, or focus. The location couldn't be better, just steps from shopping, river strolling, and amazing restaurants. "
Laura 3-night trip
Posted 3 hours ago
citizenM Chicago Downtown

Frequently asked questions

What is the nightly rate for a B&B in Historic Route 66?
Prices for B&Bs in Historic Route 66 often vary, but you can find a great deal from CA $96 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Historic Route 66 B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Historic Route 66 Bed and Breakfast and a hotel?
Every Historic Route 66 B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Historic Route 66 B&Bs.