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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured B&B in Historic Route 66 and around

Dorothy's
Relax in this stylish living area with a large sofa, glass coffee table, and patterned rug.

Dorothy's

3.0 star property
8.4 out of 10, Very good, (57)
"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."
The price is €132
includes taxes & fees
4 Aug - 5 Aug
Dorothy's
The Villa Toscana
Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (587)
"Was a great stay!"
The price is €132
includes taxes & fees
4 Aug - 5 Aug
The Villa Toscana
The Lodge at Grant's Trail
Stunning lodge-style building with a charming front porch and stone pillars.

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (440)
"Breakfasts was amazing "
The price is €148
includes taxes & fees
4 Aug - 5 Aug
The Lodge at Grant's Trail
Red Garter Inn
Enjoy the charming balcony with a metal railing and two wicker chairs.

Red Garter Inn

3.0 star property
9.6 out of 10, Exceptional, (476)
"very beautiful place to stay"
The price is €144
includes taxes & fees
4 Aug - 5 Aug
Red Garter Inn
House 5863 - Chicago Bed and Breakfast
Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

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. "
The price is €183
includes taxes & fees
4 Aug - 5 Aug
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (368)
"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! "
The price is €180
includes taxes & fees
4 Aug - 5 Aug
Ray's Bucktown B&B
Loba Luna Bed & Breakfast
Relax in the cabin's central hot tub, surrounded by views of the surrounding area.

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."
The price is €153
includes taxes & fees
6 Aug - 7 Aug
Loba Luna Bed & Breakfast
Walnut Street Inn
Cozy retreat with a four-poster bed, nightstands, and a fireplace.

Walnut Street Inn

3.5 star property
9.4 out of 10, Exceptional, (182)
"This place was cozy , welcoming, and beautiful "
The price is €110
includes taxes & fees
5 Aug - 6 Aug
Walnut Street Inn
WangShi China Palace B&B
Surrounded by lush greenery, this outdoor space features a stone column structure and a metal roof, with a pathway leading to a glass door 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 "
The price is €229
includes taxes & fees
4 Aug - 5 Aug
WangShi China Palace B&B
The Sono Chicago
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
The price is €202
includes taxes & fees
4 Aug - 5 Aug
The Sono Chicago
Trapper's Rendezvous
Charming single-story home with a front porch and a gravel driveway.

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."
The price is €148
includes taxes & fees
4 Aug - 5 Aug
Trapper's Rendezvous
The Publishing House B&B
Staircase leads to an upper level with potted plants and decorative shelves.

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!"
The price is €197
includes taxes & fees
27 Aug - 28 Aug
The Publishing House B&B
Harvey House Bed & Breakfast
Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

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"
The price is €259
includes taxes & fees
11 Aug - 12 Aug
Harvey House Bed & Breakfast
Casa Culinaria The Gourmet Inn
Relax in a serene outdoor space with a wicker sofa, chair, and table, surrounded by lush greenery and a sheltered canopy.

Casa Culinaria The Gourmet Inn

3.5 star property
9.6 out of 10, Exceptional, (250)
"Beautiful hotel on a quiet street!"
The price is €178
includes taxes & fees
4 Aug - 5 Aug
Casa Culinaria The Gourmet Inn
Harwelden Mansion
Stately brick building with a central entrance and symmetrical facade, surrounded by a beautifully maintained garden.

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. "
The price is €617
includes taxes & fees
4 Aug - 5 Aug
Harwelden Mansion
Villa D' Citta
Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (104)
"Would stay again anytime!!"
The price is €290
includes taxes & fees
6 Aug - 7 Aug
Villa D' Citta
Bobcat Inn Bed and Breakfast
Relax in a serene outdoor setting with a covered patio and peaceful pond.

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
Guests can enjoy a serene natural setting from this charming balcony with a scalloped edge, surrounded by lush greenery and beautiful flowers.

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 "
Inn Of The Turquoise Bear
Central West End B&B
Cozy retreat with a fireplace, round table, and large mirror.

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."
The price is €179
includes taxes & fees
5 Aug - 6 Aug
Central West End B&B
El Farolito Bed & Breakfast Inn
Experience a serene retreat amidst lush greenery and a charming entrance.

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."
The price is €245
includes taxes & fees
18 Aug - 19 Aug
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"🤘"
Ronald 1-night trip
Posted 18 hours ago
Freehand Chicago