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Check prices for these dates

Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Featured B&B in Historic Route 66

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 P4,186
P6,922 total
includes taxes & fees
Aug 3 - Aug 4
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 P5,058
P8,232 total
includes taxes & fees
Aug 3 - Aug 4
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, (439)
"Breakfasts was amazing "
The price is P8,545
P9,826 total
includes taxes & fees
Aug 3 - Aug 4
The Lodge at Grant's Trail
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, (475)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
The price is P8,244
P12,952 total
includes taxes & fees
Aug 3 - Aug 4
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 P11,256
P12,707 total
includes taxes & fees
Aug 4 - Aug 5
Ray's Bucktown B&B
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 P8,129
P9,584 total
includes taxes & fees
Aug 4 - Aug 5
Red Garter Inn
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 P6,452
P7,323 total
includes taxes & fees
Aug 3 - Aug 4
Walnut Street Inn
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 P9,570
P10,163 total
includes taxes & fees
Aug 1 - Aug 2
Loba Luna Bed & Breakfast
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 P12,903
P15,210 total
includes taxes & fees
Aug 1 - Aug 2
WangShi China Palace B&B
Wicker Park Inn
Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (249)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
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 P12,318
P14,461 total
includes taxes & fees
Aug 4 - Aug 5
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 P9,489
P11,187 total
includes taxes & fees
Aug 6 - Aug 7
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 P11,810
P13,333 total
includes taxes & fees
Aug 20 - Aug 21
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 P15,025
P17,201 total
includes taxes & fees
Aug 6 - Aug 7
Harvey House Bed & Breakfast
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 P17,081
P20,052 total
includes taxes & fees
Aug 6 - Aug 7
Villa D' Citta
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 P36,129
P41,013 total
includes taxes & fees
Aug 9 - Aug 10
Harwelden Mansion
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
Elden Trails Bed and Breakfast
Enjoy the serene surroundings from this outdoor deck, featuring a covered space and a comfortable seating area.

Elden Trails Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (115)
"Very pleasant stay. Situated well for the things we wanted to do in the area."
The price is P10,151
P11,285 total
includes taxes & fees
Aug 7 - Aug 8
Elden Trails 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
Four Kachinas Bed & Breakfast Inn
Enjoy a casual dining experience on the patio with a round table, comfortable chairs, and a beautiful potted plant.

Four Kachinas Bed & Breakfast Inn

3.5 star property
9.8 out of 10, Exceptional, (112)
"Friendly staff, good food,nice room, near plaza"
The price is P14,143
P16,291 total
includes taxes & fees
Aug 3 - Aug 4
Four Kachinas 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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"This place was awesome ! Very conveniently located walking distance from everywhere ! My room was very spacious, great bathroom lighting with mirror, the shower was really big. The view of the city from my room was really nice. We didn't eat at the restaurant in the hotel but it's great food options around the hotel. All of the staff were nice friendly and helpful. Breakfast was okay and you get 2 complementary drinks with your stay ! 10/10 would definitely stay again ! "
Jocelyn 2-night trip
Posted 7 hours ago
Embassy Suites by Hilton Chicago Downtown River North