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Check prices for these dates

Next weekend
Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
In one month
Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Featured B&B in Historic Route 66

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (521)
"Awesome"
The price is P1,820
P4,484 total
includes taxes & fees
Jan 27 - Jan 28
The Villa Toscana
Red Garter Inn
Terrace/patio

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (426)
"Love the rooms and how it feels like a home rather than a hotel. Everything was in walking distance to get to. "
The price is P8,269
P9,749 total
includes taxes & fees
Feb 9 - Feb 10
Red Garter Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (443)
"Our stay at The Sono was great! We were only staying a night and booked a queen room, and they gave us a free upgrade to a king room since it was unoccupied. The room was fantastic & clean, the breakfast was delicious with lots of variety and the voucher for free street parking made this the best option for our stay. I would definitely stay again."
The Sono Chicago
Trapper's Rendezvous
Front of property

Trapper's Rendezvous

4.0 star property
9.8 out of 10, Exceptional, (23)
"Feels like a luxury cabin. Great place to stop by and I would definitely consider going back to that location. "
The price is P8,451
P9,963 total
includes taxes & fees
Jan 29 - Jan 30
Trapper's Rendezvous
Casa Culinaria The Gourmet Inn
Meeting facility

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (228)
"What a gem this is! The brunch was excellent. We throughly enjoyed our stay."
The price is P6,163
P7,099 total
includes taxes & fees
Jan 26 - Jan 27
Casa Culinaria The Gourmet Inn
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (166)
"Was surprisingly excellent "
The price is P8,820
P9,957 total
includes taxes & fees
Feb 6 - Feb 7
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, (120)
"I particularly valued the opportunity to speak with the owner about the history of the property and my family's connection to it. I felt very much at home."
The price is P8,803
P10,179 total
includes taxes & fees
Jan 27 - Jan 28
Bottger Mansion of Old Town
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is P10,667
P12,522 total
includes taxes & fees
Jan 30 - Jan 31
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (340)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is P10,143
P11,451 total
includes taxes & fees
Jan 26 - Jan 27
Ray's Bucktown B&B
The Lodge at Grant's Trail
Exterior

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (377)
"The rooms were clean. Our room needs a little TLC as it had some small dents in the wall. But the room had very nice ambience. Also, your only pillow choices are "Memory Foam" pillows which were incredibly firm. I am not a memory foam pillow sleeper, and so it felt like I was sleeping on a "brick" all night. It would be nice if the inn offered at least 1 or 2 pillows that were not memory foam."
The price is P8,692
P9,995 total
includes taxes & fees
Jan 26 - Jan 27
The Lodge at Grant's Trail
Benton Park Inn
Front of property

Benton Park Inn

3.5 star property
9.6 out of 10, Exceptional, (270)
"Host and historic home."
The price is P8,109
P9,481 total
includes taxes & fees
Jan 27 - Jan 28
Benton Park Inn
Loba Luna Bed & Breakfast
Indoor spa tub

Loba Luna Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (48)
"Place is so amazing! Danny and Sarah are fantastic hosts. Also, their breakfast is better than any hotel chain. They use non seed oils (avocado oil and EVOO) and organic ingredients! "
The price is P12,413
P13,181 total
includes taxes & fees
Jan 26 - Jan 27
Loba Luna Bed & Breakfast
WangShi China Palace B&B
Property entrance

WangShi China Palace B&B

3.5 star property
9.6 out of 10, Exceptional, (77)
"Absolutely beautiful! "
The price is P13,126
P15,472 total
includes taxes & fees
Jan 26 - Jan 27
WangShi China Palace 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, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is P13,476
P14,955 total
includes taxes & fees
Jan 27 - Jan 28
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is P12,008
P14,097 total
includes taxes & fees
Jan 27 - Jan 28
Villa D' Citta
Red Horse Bed and Breakfast
Gazebo

Red Horse Bed and Breakfast

3.5 star property
9.8 out of 10, Exceptional, (227)
"Simply Magical 💫"
The price is P9,561
P10,153 total
includes taxes & fees
Jan 27 - Jan 28
Red Horse Bed and Breakfast
Sheridan House Inn - Adult Only
Private spa tub

Sheridan House Inn - Adult Only

4.0 star property
10.0 out of 10, Exceptional, (168)
"Great Stay, great property. Dinner was awesome "
The price is P15,094
P17,796 total
includes taxes & fees
Jan 27 - Jan 28
Sheridan House Inn - Adult Only
Harwelden Mansion
Front of property

Harwelden Mansion

3.5 star property
10.0 out of 10, Exceptional, (21)
"Wonderful place to stay we will be back!"
The price is P34,710
P39,402 total
includes taxes & fees
Jan 26 - Jan 27
Harwelden Mansion
Elden Trails Bed and Breakfast
Terrace/patio

Elden Trails Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (112)
"Friendly staff, right by hiking trails"
The price is P9,859
P10,961 total
includes taxes & fees
Jan 26 - Jan 27
Elden Trails Bed and Breakfast
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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Other property types in Historic Route 66

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (663)
"We stayed at Sentral after a trip to the Shedd with the kids. We had a great day and evening in the city and when we finally got to our room, we couldn't believe it! It was so spacious, we could have stayed for a week. Full kitchen, stocked with appliances, utensils, plates and glasses. Two full baths, two bedrooms and more closet space than we could have possibly used. Location was close to everything you'd need. We'll definitely be back."
The price is P6,397
P9,221 total
includes taxes & fees
Jan 26 - Jan 27
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (421)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is P5,646
P6,628 total
includes taxes & fees
Feb 25 - Feb 26
Sonder South Wabash
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1957)
"Excellent just a few insects here and there it’s a cabin so whatever but the screen on the front door didn’t work which was a little strange. Over all excellent experience very relaxing."
The price is P10,413
P11,965 total
includes taxes & fees
Jan 26 - Jan 27
Junipine Resort
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.