Five Star Hotels in Historic Route 66

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Check availability on Historic Route 66 5 Star Hotels

Top 5 Stars Hotels in Historic Route 66

The Peninsula Chicago
Stylish hotel building with a unique architectural design, set amidst a vibrant urban landscape.

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1002)
"Always love our stay at The Peninsula! "
The price is S$939
includes taxes & fees
13 Jul - 14 Jul
The Peninsula Chicago
The Langham, Chicago
Relax in our spacious lobby with a central seating area, reception desk, and stunning city views.

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1006)
"I had such a lovely staycation, and I recommend a stay here to everyone I know. "
The price is S$765
includes taxes & fees
10 Aug - 11 Aug
The Langham, Chicago
Four Seasons Hotel Chicago
Experience the grandeur of our lobby, featuring a grand staircase and elegant floral arrangements.

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (999)
"great hotel and close to all the activite"
The price is S$811
includes taxes & fees
10 Aug - 11 Aug
Four Seasons Hotel Chicago
Trump International Hotel & Tower Chicago
Panoramic city views of a historic clock tower and modern skyscraper, set against a serene river and bridge.

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1626)
"Great hotel with great staff."
The price is S$704
includes taxes & fees
20 Jul - 21 Jul
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"The room service and overall staff at this property is excellent "
The price is S$812
includes taxes & fees
3 Aug - 4 Aug
Waldorf Astoria Chicago
Rosewood Inn of the Anasazi
Welcome to the Inn of the Anasazi, a traditional hotel with a charming entrance.

Rosewood Inn of the Anasazi

5.0 star property
9.4 out of 10, Exceptional, (831)
"Ou favorite place to stay"
The price is S$777
includes taxes & fees
21 Jul - 22 Jul
Rosewood Inn of the Anasazi
Nobu Hotel Chicago
Relax by the pool with steps leading into the water and comfortable seating.

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (691)
"Always a great stay! Staff are amazing and attentive! Will be back. Also great neighborhood for walking and amazing food options. "
The price is S$778
includes taxes & fees
13 Jul - 14 Jul
Nobu Hotel Chicago
Four Seasons Hotel St Louis
Relax by the fire pit in our rooftop lounge, surrounded by comfortable seating and a bar area.

Four Seasons Hotel St Louis

5.0 star property
9.4 out of 10, Exceptional, (1000)
"The staff were professional, courteous and very attentive. Sat poolside for two days and had a great time!"
The price is S$741
includes taxes & fees
13 Jul - 14 Jul
Four Seasons Hotel St Louis
The Ritz-Carlton, St. Louis
Dine al fresco with a view of the surrounding cityscape from this outdoor dining area.

The Ritz-Carlton, St. Louis

5.0 star property
9.2 out of 10, Wonderful, (537)
"Great place"
The price is S$863
includes taxes & fees
13 Jul - 14 Jul
The Ritz-Carlton, St. Louis
Park Hyatt Chicago
Enjoy dining on the rooftop with a city view.

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Superb customer service, clean hotel!"
The price is S$794
includes taxes & fees
12 Jul - 13 Jul
Park Hyatt Chicago
The St. Regis Chicago
Relax by the pool with a panoramic city view.

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (71)
"Excellent service! Always a great time! "
The price is S$900
includes taxes & fees
10 Aug - 11 Aug
The St. Regis Chicago
The Ritz-Carlton, Chicago
Standing tall in the heart of the city, this high-rise building boasts a unique grid-like facade and a striking vertical structure.

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1002)
"Best hotel in Chicago "
The price is S$727
includes taxes & fees
10 Aug - 11 Aug
The Ritz-Carlton, Chicago
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
Relax by the serene pool surrounded by lush greenery and flowering plants, with lounge chairs and a table for a peaceful evening.

La Posada de Santa Fe, A Tribute Portfolio Resort & Spa

5.0 star property
8.2 out of 10, Very good, (1003)
"It's an amazing property, quiet, historic, and quintessentially Santa Fe but not cliche."
The price is S$435
includes taxes & fees
3 Aug - 4 Aug
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
Bishop's Lodge Auberge Resorts Collection
Cozy seating area with a stone fireplace, sofas, and a leather couch.

Bishop's Lodge Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (74)
"Great place "
Bishop's Lodge Auberge Resorts Collection
Four Seasons Resort Rancho Encantado Santa Fe
Relax in the outdoor seating area surrounded by a central fire feature and lanterns.

Four Seasons Resort Rancho Encantado Santa Fe

5.0 star property
9.4 out of 10, Exceptional, (260)
"Beautiful property … amazing staff I think that is the most valuable asset of this four seasons. B they made our stay wonderful and went out of their way to make us comfortable.. highly recommend it ."
The price is S$1,170
includes taxes & fees
27 Jul - 28 Jul
Four Seasons Resort Rancho Encantado Santa Fe
The Inn of The Five Graces
Stunning archways and intricate patterns line this elegant corridor, leading to a room with a unique view.

The Inn of The Five Graces

5.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful accommodations and a stellar staff made this stay so memorable. "
The price is S$1,806
includes taxes & fees
26 Jul - 27 Jul
The Inn of The Five Graces
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Historic Route 66.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL
The price is S$330 per night from 7 Aug to 8 Aug
S$330
7 Aug - 8 Aug
includes taxes & fees
8.4/10 Very Good! (4,376 reviews)
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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.

Learn more about Historic Route 66

Venture to sights like National Route 66 Museum and Skelly Field at H.A. Chapman Stadium as you discover Historic Route 66.

See all hotels in Historic Route 66
Tulsa featuring a river or creek, a skyscraper and a city

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Historic Route 66?
There are a range of pricing options for a 5-star hotel in Historic Route 66 on Expedia. The amount you pay will depend on when you travel, length of stay and other factors. Compare all of the available accommodation for your desired dates and make use of our pricing and other filters to lock in the ideal luxury stay.

  • Search for the lowest price per night from S$269

What makes a hotel 5 stars in Historic Route 66?
In Historic Route 66, a hotel is required to offer a specific number of high-end amenities to earn a 5-star rating. These can include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their outstanding standard of service. You can look forward to things like in-room massages, nightly turn-down services and concierge services. Some may even offer additional touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Historic Route 66?
Use our handy filters to find an upscale retreat in Historic Route 66 where everything you need is included in the price. After your initial search, refine your results for resorts that have a rating of 5 stars and are categorized as "All inclusive." The most important thing to look forward to at these stays? Pure indulgence and relaxation.