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Check prices for these dates

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

B&B in Historic Route 66

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (58)
"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."
$123 nightly
The price is $138
Aug 6 - Aug 7
Total includes taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
$132 nightly
The price is $148
Aug 6 - Aug 7
Total includes taxes and fees
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 "
$133 nightly
The price is $154
Aug 10 - Aug 11
Total includes taxes and fees
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"
$149 nightly
The price is $175
Aug 10 - Aug 11
Total includes taxes and fees
Red Garter Inn
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (476)
"Everything was taken care of! A wonderful stay. "
$180 nightly
The price is $212
Aug 6 - Aug 7
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast
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! "
$174 nightly
The price is $196
Aug 6 - Aug 7
Total includes taxes and fees
Ray's Bucktown 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."
$167 nightly
The price is $177
Aug 6 - Aug 7
Total includes taxes and fees
Loba Luna Bed & Breakfast
Walnut Street Inn
Suite, 1 Queen Bed | 1 bedroom, individually decorated, individually furnished

Walnut Street Inn

3.5 star property
9.4 out of 10, Exceptional, (183)
"This place was cozy , welcoming, and beautiful "
$125 nightly
The price is $142
Aug 6 - Aug 7
Total includes taxes and fees
Walnut Street Inn
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 "
$225 nightly
The price is $265
Aug 6 - Aug 7
Total includes taxes and fees
WangShi China Palace B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
$184 nightly
The price is $216
Aug 6 - Aug 7
Total includes taxes and fees
The Sono Chicago
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."
$165 nightly
The price is $195
Aug 6 - Aug 7
Total includes taxes and fees
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!"
$163 nightly
The price is $185
Sep 4 - Sep 5
Total includes taxes and fees
The Publishing House B&B
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"
$262 nightly
The price is $300
Aug 11 - Aug 12
Total includes taxes and fees
Harvey House Bed & 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!"
$199 nightly
The price is $229
Aug 7 - Aug 8
Total includes taxes and fees
Casa Culinaria The Gourmet 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. "
$700 nightly
The price is $795
Aug 6 - Aug 7
Total includes taxes and fees
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!!"
$263 nightly
The price is $309
Aug 6 - Aug 7
Total includes taxes and fees
Villa D' Citta
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
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 "
$389 nightly
The price is $448
Aug 12 - Aug 13
Total includes taxes and fees
Inn Of The Turquoise Bear
Central West End B&B
(Lil Dynasty) No Private Bathroom | Premium bedding, iron/ironing board, free WiFi, bed sheets

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."
$163 nightly
The price is $191
Aug 18 - Aug 19
Total includes taxes and fees
Central West End B&B
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."
$247 nightly
The price is $284
Aug 12 - Aug 13
Total includes taxes and fees
El Farolito Bed & Breakfast Inn
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great location! Clean rooms. Comfy beds. "
Nicole 2-night trip
Posted 3 hours ago
Crowne Plaza Chicago West Loop by IHG