Five Star Hotels in Historic Route 66

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Historic Route 66 5 Star Hotels

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Historic Route 66 5 Stars Hotels

Trump International Hotel & Tower Chicago
Enjoy breathtaking views of the city skyline from the expansive window.

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1680)
"Great hotel "
The price is RM1,958
RM2,299 total
includes taxes & fees
7 Sept - 8 Sept
Trump International Hotel & Tower 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 location and amenities!"
The price is RM2,441
RM2,865 total
includes taxes & fees
7 Sept - 8 Sept
Four Seasons Hotel 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, (1002)
"Very nice location super friendly staff very modern and clear hotel "
The price is RM2,308
RM2,710 total
includes taxes & fees
31 Aug - 1 Sept
The Langham, Chicago
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, (1001)
"Excellent very clean Quiet great location"
The price is RM2,648
RM3,108 total
includes taxes & fees
24 Aug - 25 Aug
The Peninsula Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great location "
The price is RM2,384
RM2,798 total
includes taxes & fees
1 Sept - 2 Sept
Waldorf Astoria Chicago
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, (707)
"Beautiful, staffed with great people."
The price is RM2,013
RM2,363 total
includes taxes & fees
10 Aug - 11 Aug
Nobu Hotel Chicago
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, (540)
"Wish they still had a pool"
The price is RM2,453
RM2,857 total
includes taxes & fees
10 Aug - 11 Aug
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, (1001)
"It's a beautiful and comfortable hotel."
The price is RM2,381
RM2,796 total
includes taxes & fees
8 Sept - 9 Sept
Park Hyatt Chicago
The Ritz-Carlton, Chicago
Relax in the contemporary lobby with a central bar area, featuring a geometric patterned floor and comfortable seating.

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful place "
The price is RM2,089
RM2,452 total
includes taxes & fees
7 Sept - 8 Sept
The Ritz-Carlton, 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)
"We’ve stayed at this hotel several times and keep coming back. Great hotel staff and property. "
The price is RM1,800
RM2,105 total
includes taxes & fees
20 Aug - 21 Aug
Four Seasons Hotel St Louis
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, (836)
"Loved this hotel! Gorgeous rooms."
The price is RM2,033
RM2,571 total
includes taxes & fees
13 Aug - 14 Aug
Rosewood Inn of the Anasazi
The St. Regis Chicago
Enjoy a sophisticated dining experience with unobstructed views of the city.

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (72)
"Amazing hotel"
The price is RM2,499
RM2,934 total
includes taxes & fees
1 Sept - 2 Sept
The St. Regis Chicago
Bishop's Lodge Auberge Resorts Collection
Guests can enjoy a peaceful evening in this serene outdoor space surrounded by trees and lush vegetation.

Bishop's Lodge Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (77)
"Close to downtown but everything you would want in a high end resort from stargazing to horseback riding to quality restaurant and pool with attentive and friendly staff"
Bishop's Lodge Auberge Resorts Collection
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
Stroll through the serene garden, surrounded by a central water feature, well-manicured flower beds, and a variety of shrubs.

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

5.0 star property
8.2 out of 10, Very good, (1003)
"Beautiful and relaxing."
The price is RM1,102
RM1,439 total
includes taxes & fees
24 Aug - 25 Aug
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
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, (261)
"Food options were good, but limited. The scenery was breathtaking as well as the nearby Santa Fe and the tours we took to the Indian reservation and Los Alamos"
The price is RM2,887
RM3,479 total
includes taxes & fees
7 Sept - 8 Sept
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 Inn of The Five Graces
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL
The price is RM736 per night from 22 Aug to 23 Aug
RM736
RM970 total
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
Still don't see what you're looking for?
See all properties in Historic Route 66.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 which includes a city, a sunset and a river or creek

Top Historic Route 66 Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Historic Route 66?
The amount you pay for a 5-star hotel in Historic Route 66 can vary depending on the time of year you travel and how long you plan to stay, among other factors. Take advantage of our price per night filter and other search tools to score the best rate on a luxurious stay.

  • Search for the lowest price per night from RM568

What makes a hotel 5 stars in Historic Route 66?
In Historic Route 66, a hotel must offer a specific number of upscale amenities to earn 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their superior service. You can expect things like nightly turn-down services, in-room massages and concierge services. Some may even offer special touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Historic Route 66?
Use Expedia's filters to find a high-end retreat in Historic Route 66 where most of what you need is included in the price. From there, narrow down your results for accommodation that have a 5-star rating and are categorised as "All inclusive." The first thing on the agenda at these stays? Pure relaxation and indulgence.