Find a Bed and Breakfast in Historic Route 66 from CA $56

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Browse Select Historic Route 66 B&B

The Villa Toscana
Double Room, Private Bathroom (Venetian) | Exterior
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 $121 total
includes taxes & fees
Jun 6 - Jun 7
The Villa Toscana
Old Chicago Inn
Fireplace
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
Property entrance
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 $310
CA $383 total
includes taxes & fees
Jul 1 - Jul 2
Wicker Park Inn
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Casa Culinaria The Gourmet Inn
Meeting facility
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 $300
CA $345 total
includes taxes & fees
Jun 9 - Jun 10
Casa Culinaria The Gourmet Inn
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, 291 reviews
"What a gem! Beautiful neighborhood, close to restaurants, shopping and the surrounding area is so pretty. The place itself is so warm, quirky and set up so well! We got a garage spot to park which was bonus! The cooked to order breakfast was delicious and the staff were so friendly! Communication was excellent and check in was super smooth. Highly recommend Ray’s Bucktown B & B! "
The price is CA $245
CA $277 total
includes taxes & fees
Jun 24 - Jun 25
Ray's Bucktown B&B
Benton Park Inn
Front of property
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 $185
CA $217 total
includes taxes & fees
Jun 16 - Jun 17
Benton Park Inn
House 5863 - Chicago Bed and Breakfast
Exterior
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 $332 total
includes taxes & fees
Jun 11 - Jun 12
House 5863 - Chicago Bed and Breakfast
The Sono Chicago
Private kitchen
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, 419 reviews
"The Sono is a terrific property and highly recommended. Rooms are lovely, the common areas are outstanding, we enjoyed hanging out with our traveling group along with a frig stocked with waters. Breakfast in the morning is a really nice feature. The only drawback is the location in a largely residential area. Yet it is an easy walk or Uber downtown. I would highly recommend the property and special thanks to Addie. "
The price is CA $249
CA $293 total
includes taxes & fees
Jun 17 - Jun 18
The Sono Chicago
The Lodge at Grant's Trail
Exterior
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 $171
CA $197 total
includes taxes & fees
Jun 10 - Jun 11
The Lodge at Grant's Trail
Red Garter Inn
Classic Room, 2 Queen Beds | Terrace/patio
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 25 - Jun 26
Red Garter Inn
Trapper's Rendezvous
Front of property
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 $263 total
includes taxes & fees
Jun 6 - Jun 7
Trapper's Rendezvous
The Publishing House B&B
Staircase
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
Outdoor dining
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 $281
CA $324 total
includes taxes & fees
Jul 4 - Jul 5
Bottger Mansion of Old Town
Dos Hermanas Compound 7 Casitas Sleeps 22
Exterior
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 24 - Jun 25
Dos Hermanas Compound 7 Casitas Sleeps 22
Loba Luna Bed & Breakfast
Indoor spa tub
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 14 - Jun 15
Loba Luna Bed & Breakfast
Red Horse Bed and Breakfast
Gazebo
Red Horse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, 220 reviews
"Peaceful stay--a great respite on a long journey. Great shower, bathroom, and bed. Thanks Darlene for the delicious breakfast and Phil for your hospitality. Our one complaint was that we could not take our dog off leash because it was not fully fenced in. "
Red Horse Bed and Breakfast
Villa D' Citta
Lobby sitting area
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, 81 reviews
"Very nice place to stay in the Lincoln Park area. Comfortable rooms and wonderful amenities."
The price is CA $313
CA $367 total
includes taxes & fees
Jun 24 - Jun 25
Villa D' Citta
Elden Trails Bed and Breakfast
Terrace/patio
Elden Trails Bed and Breakfast
3.0 star property
9.0 out of 10, Wonderful, 106 reviews
"Super friendly very helpful would stay again and again"
The price is CA $218
CA $242 total
includes taxes & fees
Jun 9 - Jun 10
Elden Trails Bed and Breakfast
WangShi China Palace B&B
Property entrance
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 14 - Jun 15
WangShi China Palace B&B
Harvey House Bed & Breakfast
Property entrance
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
Jun 13 - Jun 14
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
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 426 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 $245
CA $328 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, 94 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 $117
CA $138 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 309 reviews
"Sonder rocks!"
The price is CA $249
CA $293 total
includes taxes & fees
Jun 9 - Jun 10
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

Number of reviews
3,888
Accommodation
22 B&B
Lowest Price
CA $56
Highest Price
CA $357

Recent Reviews in Historic Route 66
Expedia verified reviews

Central Loop Hotel

Central Loop Hotel

5/5 Excellent
"Very central location, clean, friendly staff, and affordable."
A verified traveller stayed at Central Loop Hotel
Posted 17 hours ago
Central Loop Hotel