Find a Bed and Breakfast in Historic Route 66

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Browse Select Historic Route 66 B&B

The Villa Toscana
2.5 star property
7.6 out of 10, Good, 430 reviews
"GREAT stay and location! Very COZY and near LOTS of shops, restaurants, clubs, CTA, etc! Only thing is it's HUMANLESS Check-in/Out! All Communication/Codes are sent via email or text!"
The price is CA $56
CA $120 total
includes taxes & fees
Jun 5 - Jun 6
The Villa Toscana
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, 731 reviews
"Everything was winderful and i really enjoy my stay at Old Chicago Inn. The rooms are cute, everything is very secure, and staff is super friends and accommodating. I look forward to booking again with you soon! "
Old Chicago Inn
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, 219 reviews
"We really enjoyed our stay at the Wicker Park Inn. Nestled in a quiet street with many trees and birds it’s very peaceful and relaxing. There is a tram that runs behind the building periodically but it’s not a harsh sound, kind of pleasant to be honest, like a wave or roll of thunder that comes and goes. The Inn itself is spotless, comfortable and well appointed with great attention to detail. It’s obvious the owners understand the needs of their guests. The location is perfect, just a block...
The price is CA $309
CA $381 total
includes taxes & fees
Jul 1 - Jul 2
Wicker Park Inn
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Casa Culinaria The Gourmet Inn
3.5 star property
9.6 out of 10, Exceptional, 196 reviews
"AMAZING. Don't wait! "
The price is CA $271
CA $312 total
includes taxes & fees
Jun 5 - Jun 6
Casa Culinaria The Gourmet Inn
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, 290 reviews
"This is a great property to stay at while in Chicago. Many bars and restaurants nearby as well as easy to get to public transportation. Staff and breakfast are incredible. "
The price is CA $245
CA $277 total
includes taxes & fees
Jun 24 - Jun 25
Ray's Bucktown B&B
Benton Park Inn
3.5 star property
9.6 out of 10, Exceptional, 235 reviews
"We had a wonderful stay at the Benton Park Inn. Dan and his dog Rosie were very welcoming. The suite was spacious and comfortable. Breakfast was divine! Loved the Benton Park historic neighborhood, easy to walk to good restaurants from the Inn. We were not big B&B people but after this experience we will be back!"
The price is CA $172
CA $202 total
includes taxes & fees
Jul 4 - Jul 5
Benton Park Inn
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, 463 reviews
"Great traditional bnb. Friendly staff. Great patio. Comfortable and clean"
The price is CA $215
CA $331 total
includes taxes & fees
Jun 5 - Jun 6
House 5863 - Chicago Bed and Breakfast
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, 419 reviews
"Perfect choice while in town for a nearby family wedding. On a quiet leafy street, two blocks off commercial North Ave. Three story walk-up row house, only a few rooms, full kitchen/living room where continental breakfast is served daily, or on back deck. Loved our balcony room, a spacious king. Clean and newly painted. Friendly helpful staff. Only issue could be the street parking - and you do need a car to get around. You’re in a residential neighborhood with a school across the street....
The price is CA $268
CA $315 total
includes taxes & fees
Jun 13 - Jun 14
The Sono Chicago
The Lodge at Grant's Trail
3.5 star property
9.6 out of 10, Exceptional, 345 reviews
"My husband and I brought our toddler granddaughter here for the weekend and it was a wonderful venue ! The staff is amazing, breakfast was delicious and made to order. It was a great experience and we look forward to going back soon. "
The price is CA $201
CA $232 total
includes taxes & fees
Jun 12 - Jun 13
The Lodge at Grant's Trail
Red Garter Inn
3.0 star property
9.6 out of 10, Exceptional, 387 reviews
"It was like we were transported in a time capsule to 1890. The place is perfectly renovated and maintained. Very clean, cozy and comfortable. There was even fresh flowers in the room. We received excellent directions for check in and check out via text message. Many good restaurants within 3-5 min walk. I would highly recommend it to anyone who likes history. "
The price is CA $204
CA $241 total
includes taxes & fees
Jun 19 - Jun 20
Red Garter Inn
Trapper's Rendezvous
4.0 star property
9.8 out of 10, Exceptional, 12 reviews
"Absolutely beautiful. Very comfortable beds and homey feeling."
The price is CA $223
CA $262 total
includes taxes & fees
Jun 5 - Jun 6
Trapper's Rendezvous
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, 149 reviews
"Unique and bespoke style. Great west loop location "
The price is CA $316
CA $357 total
includes taxes & fees
Jun 16 - Jun 17
The Publishing House B&B
Bottger Mansion of Old Town
3.5 star property
9.6 out of 10, Exceptional, 103 reviews
"Excellent breakfast Charming room Nice neighborhood "
The price is CA $265
CA $306 total
includes taxes & fees
Jun 26 - Jun 27
Bottger Mansion of Old Town
Dos Hermanas Compound 7 Casitas Sleeps 22
3.0 star property
10.0 out of 10, Exceptional, 1 review
"I loved staying in a studio here. It was cute, comfy, and had everything I needed. I make sure you read the check in emails prior to arriving and it’s best to arrive in the day time because it’s kind of, but owners were responsive via text. Other than that, the place was lovely! "
The price is CA $270
CA $427 total
includes taxes & fees
Jun 17 - Jun 18
Dos Hermanas Compound 7 Casitas Sleeps 22
Loba Luna Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, 33 reviews
"We enjoyed our stay, the owners were great! The home was amazing and the food was delicious. "
The price is CA $290
CA $308 total
includes taxes & fees
Jun 5 - Jun 6
Loba Luna Bed & Breakfast
Red Horse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, 220 reviews
"Greeted warmly. Phil told us all about the interesting property history. Darlene is an excellent cook. They made feel as if we were part of the family in a very good way. We would be happy to stay there with out a doubt."
Red Horse Bed and Breakfast
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, 80 reviews
"Very nice place to stay in the Lincoln Park area. Comfortable rooms and wonderful amenities."
The price is CA $312
CA $366 total
includes taxes & fees
Jun 24 - Jun 25
Villa D' Citta
Elden Trails Bed and Breakfast
3.0 star property
9.0 out of 10, Wonderful, 106 reviews
"This is a cute studio behind the main house. I loved the chickens, gardens and being able to hike right out the back door. Nice people, comfortable bed and clean. Thank you!! "
The price is CA $217
CA $241 total
includes taxes & fees
Jun 9 - Jun 10
Elden Trails Bed and Breakfast
WangShi China Palace B&B
3.5 star property
9.6 out of 10, Exceptional, 67 reviews
"Very nice B&B! Staff was very helpful and the property is very unique. "
The price is CA $307
CA $350 total
includes taxes & fees
Jun 7 - Jun 8
WangShi China Palace B&B
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, 94 reviews
"Another amazingly relaxing stay at the Harvey House! Highly recommend it."
The price is CA $357
CA $396 total
includes taxes & fees
Jul 3 - Jul 4
Harvey House Bed & Breakfast
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See all available properties in Historic Route 66
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.

Other property types in Historic Route 66

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 424 reviews
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is CA $244
CA $327 total
includes taxes & fees
Jul 3 - Jul 4
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, 92 reviews
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is CA $125
CA $147 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 309 reviews
"Sonder rocks!"
The price is CA $277
CA $325 total
includes taxes & fees
Jul 2 - Jul 3
Sonder South Wabash
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.

Historic Route 66 B&B information

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