Five Star Hotels in Historic Route 66

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Check availability on Historic Route 66 5 Star Hotels

Tonight
24 Jul - 25 Jul
Tomorrow
25 Jul - 26 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top 5 Stars Hotels in Historic Route 66

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1662)
"Great hotel "
The price is S$702
includes taxes & fees
3 Aug - 4 Aug
Trump International Hotel & Tower Chicago
The Peninsula Chicago
Front of property – evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1008)
"Excellent very clean Quiet great location"
The price is S$936
includes taxes & fees
24 Aug - 25 Aug
The Peninsula Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1008)
"I had such a lovely staycation, and I recommend a stay here to everyone I know. "
The price is S$815
includes taxes & fees
24 Aug - 25 Aug
The Langham, Chicago
Four Seasons Hotel Chicago
Reception

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$802
includes taxes & fees
24 Aug - 25 Aug
Four Seasons Hotel Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (700)
"Beautiful, staffed with great people."
The price is S$587
includes taxes & fees
27 Jul - 28 Jul
Nobu Hotel Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1005)
"The room service and overall staff at this property is excellent "
The price is S$810
includes taxes & fees
17 Aug - 18 Aug
Waldorf Astoria Chicago
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
Property amenity

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

5.0 star property
8.2 out of 10, Very good, (1007)
"Well located and walkable to both center of town and Canyon road. Ate there and it was delicious"
The price is S$433
includes taxes & fees
10 Aug - 11 Aug
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa
Four Seasons Hotel St Louis
Rooftop bar

Four Seasons Hotel St Louis

5.0 star property
9.4 out of 10, Exceptional, (1006)
"Great hotel, loved the room"
The price is S$739
includes taxes & fees
2 Aug - 3 Aug
Four Seasons Hotel St Louis
Park Hyatt Chicago
1 bedroom, premium bedding, down duvets, pillow-top beds

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1003)
"It's a beautiful and comfortable hotel."
The price is S$881
includes taxes & fees
22 Aug - 23 Aug
Park Hyatt Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1005)
"Beautiful place "
The price is S$713
includes taxes & fees
24 Aug - 25 Aug
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (72)
"Amazing hotel"
The price is S$898
includes taxes & fees
24 Aug - 25 Aug
The St. Regis Chicago
Rosewood Inn of the Anasazi
Exterior

Rosewood Inn of the Anasazi

5.0 star property
9.4 out of 10, Exceptional, (836)
"Loved this hotel! Gorgeous rooms."
The price is S$775
includes taxes & fees
24 Aug - 25 Aug
Rosewood Inn of the Anasazi
The Ritz-Carlton, St. Louis
Meeting facility

The Ritz-Carlton, St. Louis

5.0 star property
9.2 out of 10, Wonderful, (539)
"Wish they still had a pool"
The price is S$861
includes taxes & fees
24 Aug - 25 Aug
The Ritz-Carlton, St. Louis
Bishop's Lodge Auberge Resorts Collection
Exterior

Bishop's Lodge Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (75)
"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
Four Seasons Resort Rancho Encantado Santa Fe
Terrace/patio

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$1,167
includes taxes & fees
24 Aug - 25 Aug
Four Seasons Resort Rancho Encantado Santa Fe
The Inn of The Five Graces
Deep-tissue massages, Swedish massages, massages

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$1,801
includes taxes & fees
24 Aug - 25 Aug
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.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL
The price is S$407 per night from 22 Aug to 23 Aug
S$407
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (2,094 reviews)
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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

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?
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.