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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 24 B&B in Historic Route 66 with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (549)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is AED 378
AED 591 total
includes taxes & fees
12 May - 13 May
The Villa Toscana
Red Garter Inn
Classic Room, 2 Queen Beds | City view

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (454)
"Beautiful clean quiet place to stay "
The price is AED 521
AED 614 total
includes taxes & fees
25 May - 26 May
Red Garter Inn
The Lodge at Grant's Trail
Exterior

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (406)
"The lodge is simply amazing! Service is wonderful, the decor is beautiful and it's location is very convenient for our trips into St. Louis. "
The price is AED 504
AED 579 total
includes taxes & fees
14 May - 15 May
The Lodge at Grant's Trail
Walnut Street Inn
Suite, 1 Queen Bed | Individually decorated, individually furnished, iron/ironing board

Walnut Street Inn

3.5 star property
9.4 out of 10, Exceptional, (167)
"Very friendly and helpful staff. The room was lovely "
The price is AED 444
AED 504 total
includes taxes & fees
20 May - 21 May
Walnut Street Inn
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (172)
"Amazing stay! Great location and beautiful hotel that made you feel cozy"
The price is AED 837
AED 945 total
includes taxes & fees
26 May - 27 May
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (349)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is AED 619
AED 699 total
includes taxes & fees
12 May - 13 May
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very Good, (32)
"We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!"
The price is AED 345
AED 534 total
includes taxes & fees
21 May - 22 May
Dorothy's
Trapper's Rendezvous
Front of property

Trapper's Rendezvous

4.0 star property
9.8 out of 10, Exceptional, (28)
"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 AED 698
AED 823 total
includes taxes & fees
12 May - 13 May
Trapper's Rendezvous
Benton Park Inn
Front of property

Benton Park Inn

3.5 star property
9.6 out of 10, Exceptional, (281)
"We had a wonderful stay! Host was friendly and had great suggestions for dining and activities. The house was absolutely charming! Will definitely stay again."
The price is AED 511
AED 597 total
includes taxes & fees
15 May - 16 May
Benton Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (453)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 520
AED 611 total
includes taxes & fees
12 May - 13 May
The Sono Chicago
WangShi China Palace B&B
Property entrance

WangShi China Palace B&B

3.5 star property
9.4 out of 10, Exceptional, (86)
"Absolutely amazing we will definitely be staying again so quiet staff is nice everything is super quiet!"
The price is AED 826
AED 974 total
includes taxes & fees
12 May - 13 May
WangShi China Palace B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Great spot for a quick stay!"
The price is AED 1,010
AED 1,185 total
includes taxes & fees
19 May - 20 May
Wicker Park Inn
Bottger Mansion of Old Town
Outdoor dining

Bottger Mansion of Old Town

3.5 star property
9.6 out of 10, Exceptional, (128)
"Outstanding breakfast. "
The price is AED 646
AED 747 total
includes taxes & fees
27 May - 28 May
Bottger Mansion of Old Town
Casa Culinaria The Gourmet Inn
Terrace/patio

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (246)
"The owners (man/wife) were wonderful, very personable. The Chef (the wife) was amazing and her brunches were incomparable!"
The price is AED 694
AED 800 total
includes taxes & fees
12 May - 13 May
Casa Culinaria The Gourmet Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is AED 841
AED 987 total
includes taxes & fees
12 May - 13 May
Villa D' Citta
Loba Luna Bed & Breakfast
Indoor spa tub

Loba Luna Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (57)
"The team here was fantastic and the food was amazing! We highly recommend! "
The price is AED 613
AED 651 total
includes taxes & fees
27 May - 28 May
Loba Luna Bed & Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Awesome, comfortable stay good food options would recommend "
The price is AED 962
AED 1,068 total
includes taxes & fees
12 May - 13 May
Harvey House Bed & Breakfast
El Farolito Bed & Breakfast Inn
Garden

El Farolito Bed & Breakfast Inn

3.5 star property
9.8 out of 10, Exceptional, (86)
"Loved the decor in our room. Breakfast was very good and the staff was very attentive and friendly."
The price is AED 776
AED 894 total
includes taxes & fees
12 May - 13 May
El Farolito Bed & Breakfast Inn
Red Horse Bed and Breakfast
Gazebo

Red Horse Bed and Breakfast

3.5 star property
9.8 out of 10, Exceptional, (233)
"Staff and food were excellent. Beautiful and well maintained."
Red Horse Bed and Breakfast
Harwelden Mansion
Front of property

Harwelden Mansion

3.5 star property
10.0 out of 10, Exceptional, (26)
"Wonderful place to stay we will be back!"
The price is AED 2,057
AED 2,335 total
includes taxes & fees
13 May - 14 May
Harwelden Mansion
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, (749)
"we enjoyed the stay"
The price is AED 528
AED 727 total
includes taxes & fees
26 May - 27 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (500)
"Great stay "
The price is AED 425
AED 499 total
includes taxes & fees
27 May - 28 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (279)
"Cool location"
The price is AED 461
AED 542 total
includes taxes & fees
26 May - 27 May
Sonder Market Hall
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.