Book Bed and Breakfast in Historic Route 66

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Featured B&B in Historic Route 66

The Lodge at Grant's Trail

The Lodge at Grant's Trail

3.5 out of 5
4398 Hoffmeister Ave. St. Louis MO
$139 nightly
The price is $160 total per night
$160 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Lodge at Grant's Trail features free WiFi in public areas, conference space, and a terrace. Free parking is included with your stay. This smoke-free bed & breakfast also has wedding services.
Parking included
Free WiFi
The Sono Chicago

The Sono Chicago

3.5 out of 5
1428 N Cleveland Ave Chicago IL
$131 nightly
The price is $154 total per night
$154 total
Dec 16 - Dec 17
Total with taxes and fees
At The Sono Chicago, guests have access to a rooftop terrace, free WiFi in public areas, and a terrace. Free parking is included with your stay. Front-desk staff can assist with luggage storage and concierge services. This smoke-free bed & breakfast also has a fireplace in the lobby.
Dorothy's

Dorothy's

3 out of 5
3445 N Halsted St Chicago IL
$67 nightly
The price is $72 total per night
$72 total
Dec 17 - Dec 18
Total with taxes and fees
Guests of Dorothy's enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. If you plan to drive, free offsite parking is available. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Additional amenities include laundry facilities, local meal delivery service, and a TV in a common area.
Breakfast included
Pet friendly
The Villa Toscana

The Villa Toscana

2.5 out of 5
3447 N Halsted Chicago IL
$67 nightly
The price is $72 total per night
$72 total
Dec 16 - Dec 17
Total with taxes and fees
Guests of The Villa Toscana enjoy free WiFi in public areas, express check-in, and express check-out. You can take advantage of free parking if you drive. Helpful staff is there to provide luggage storage, as well as offer insight about the area. This adults-only bed & breakfast also has wedding services.
Red Garter Inn

Red Garter Inn

3 out of 5
137 W Railroad Ave Williams AZ
$80 nightly
The price is $95 total per night
$95 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At Red Garter Inn, guests have access to a golf course, a winery, and free WiFi in public areas. A stay here includes free parking. Other amenities at this golf bed & breakfast include coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area.
Parking included
Free WiFi
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 out of 5
2144 N. Leavitt St Chicago IL
$147 nightly
The price is $166 total per night
$166 total
Dec 16 - Dec 17
Total with taxes and fees
Guests of Ray's Bucktown B&B enjoy a rooftop terrace, free WiFi in public areas, and a 24-hour business center. If you decide to drive, there's free parking. Staff members can help with accommodation requests, and provide luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area.
The Publishing House B&B

The Publishing House B&B

3.5 out of 5
108 N May Street Chicago IL
$188 nightly
The price is $213 total per night
$213 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of The Publishing House B&B enjoy features like a winery, free WiFi in public areas, and a business center. Front-desk staff can assist with luggage storage and concierge services. Additional amenities include a microwave in a common area, a refrigerator in a common area, and a library.
Wicker Park Inn

Wicker Park Inn

3.5 out of 5
1331 N Wicker Park Ave Chicago IL
$186 nightly
The price is $218 total per night
$218 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of Wicker Park Inn enjoy access to free WiFi in public areas, meeting rooms, and spa services. Self parking is offered for USD 45.00 per night. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include express check-in, express check-out, and a garden.
Walnut Street Inn

Walnut Street Inn

3.5 out of 5
900 E Walnut Street Springfield MO
$113 nightly
The price is $128 total per night
$128 total
Dec 29 - Dec 30
Total with taxes and fees
Walnut Street Inn features free WiFi in public areas, coffee in a common area, and a meeting room. If you drive, put free parking to good use. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Additional amenities include express check-in, express check-out, and a terrace.
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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.

Hotel Options in Historic Route 66

    Club Quarters Hotel, Central Loop, Chicago

    Club Quarters Hotel, Central Loop, Chicago

    111 West Adams Street Chicago IL
    $87 nightly
    The price is $102 total per night from Dec 21 to Dec 22
    $102 total
    Dec 21 - Dec 22
    Total with taxes and fees
    8.6/10 Excellent! (3,314 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $81 nightly
    The price is $95 total per night from Jan 5 to Jan 6
    $95 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,467 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Dec 21 to Dec 22
    $149 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.2/10 Wonderful! (2,109 reviews)

Bed and Breakfast

Book a bed and breakfast in Historic Route 66
A romantic getaway awaits when you book a bed and breakfast in Historic Route 66. The beauty of renting a B&B is that each one is unique. A farm B&B is cozy and rustic, while a luxury B&B provides top-of-the-line luxuries, including in-room jet tubs and thousand thread-count sheets. And let’s not forget the most important part of its name…breakfast! Bed & breakfasts are famous for putting out a great spread each morning. Fill your plate with fluffy pancakes with maple syrup, hot eggs right from the pan, and a cup of hot coffee to help get you ready for the rest of your day.

All are welcome at Historic Route 66 bed n breakfasts
Some cheap accommodations are designed to simply give travelers a roof overhead and a comfortable bed to sleep on between adventures or business meetings. This definitely isn’t the case with a bed and breakfast (also known as a breakfast inn). The right B&B doesn’t just host your vacation to Historic Route 66, it becomes part of it. In many cases, travelers get to know the manager of the B&B, as well as mingle with other guests. Many B&Bs also arrange activities for guests, such as hikes in the area, bird watching outings, or fun game nights. 

B&B hotels have a reputation as a romantic retreat for couples. However, B&Bs are actually for all sorts of travelers. Book one with a parent, child, or your favorite travel buddy. Want to take your fur child on your adventure to Historic Route 66? A quick search through Orbitz will bring up pet-friendly B&B options so your best friend can come along.

Historic Route 66 B&B essential information

Accommodation
30 B&B
Lowest Price
$72
Highest Price
$218
Popular accommodation
The Lodge at Grant's Trail, The Sono Chicago, Dorothy's, The Villa Toscana, Red Garter Inn, Ray's Bucktown B&B, The Publishing House B&B, Wicker Park Inn, Walnut Street Inn

More to Explore