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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

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 AU$175
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, (590)
"Was a great stay!"
The price is AU$222
includes taxes & fees
24 Aug - 25 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, (443)
"Breakfasts was amazing "
The price is AU$250
includes taxes & fees
19 Aug - 20 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, (478)
"very beautiful place to stay"
The price is AU$243
includes taxes & fees
27 Aug - 28 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 AU$311
includes taxes & fees
19 Aug - 20 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, (479)
"Everything was taken care of! A wonderful stay. "
The price is AU$325
includes taxes & fees
20 Aug - 21 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 AU$317
includes taxes & fees
19 Aug - 20 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, (184)
"This place was cozy , welcoming, and beautiful "
The price is AU$196
includes taxes & fees
19 Aug - 20 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 AU$261
includes taxes & fees
24 Aug - 25 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 AU$365
includes taxes & fees
7 Sept - 8 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, (67)
"The staff was fantastic and so sweet. The property is beautiful."
The price is AU$272
includes taxes & fees
20 Aug - 21 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, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AU$461
includes taxes & fees
21 Aug - 22 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, (96)
"Excellent"
The price is AU$408
includes taxes & fees
19 Aug - 20 Aug
WangShi China Palace B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (467)
"Loved the shared kitchen access! "
The price is AU$273
includes taxes & fees
25 Aug - 26 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 AU$437
includes taxes & fees
24 Aug - 25 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 AU$1,099
includes taxes & fees
19 Aug - 20 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 AU$475
includes taxes & fees
19 Aug - 20 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 AU$318
includes taxes & fees
19 Aug - 20 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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"It was nice "
lexi 2-night trip
Posted 10 hours ago
Hilton Chicago