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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured B&B in Historic Route 66 and around

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (62)
"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 €104
includes taxes & fees
13 Aug - 14 Aug
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
The price is €114
includes taxes & fees
12 Aug - 13 Aug
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, (441)
"Breakfasts was amazing "
The price is €147
includes taxes & fees
17 Aug - 18 Aug
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, (477)
"very beautiful place to stay"
The price is €143
includes taxes & fees
20 Aug - 21 Aug
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 €179
includes taxes & fees
11 Aug - 12 Aug
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, (478)
"Everything was taken care of! A wonderful stay. "
The price is €181
includes taxes & fees
13 Aug - 14 Aug
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 €196
includes taxes & fees
20 Aug - 21 Aug
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, (183)
"This place was cozy , welcoming, and beautiful "
The price is €109
includes taxes & fees
11 Aug - 12 Aug
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 €147
includes taxes & fees
11 Aug - 12 Aug
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 €154
includes taxes & fees
4 Sept - 5 Sept
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)
"Beautiful setting. Authentic southwestern adobe home with appropriate updates, true to the era. Period furniture and decor. I'd definitely stay again."
The price is €152
includes taxes & fees
10 Aug - 11 Aug
Loba Luna Bed & Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is €257
includes taxes & fees
11 Aug - 12 Aug
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 €227
includes taxes & fees
10 Aug - 11 Aug
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 €187
includes taxes & fees
10 Aug - 11 Aug
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 €244
includes taxes & fees
12 Aug - 13 Aug
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 €613
includes taxes & fees
10 Aug - 11 Aug
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 €231
includes taxes & fees
13 Aug - 14 Aug
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 "
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 €177
includes taxes & fees
21 Aug - 22 Aug
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

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Location, room, and staff friendliness made an excellent stay. It looks renovated and that's a plus. Room was spacious, breakfast was OK. Will definitely return!"
JOSE ANTHONY 1-night trip
Posted 16 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical