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5 Star Hotels in Historic Route 66

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Featured 5 Star Historic Route 66 Hotels

Trump International Hotel & Tower Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $462 per night from Nov 24 to Nov 25
$462
includes taxes & fees
Nov 24 - Nov 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Trump International Hotel & Tower Chicago
The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $616 per night from Nov 24 to Nov 25
$616
includes taxes & fees
Nov 24 - Nov 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
The Peninsula Chicago
The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $586 per night from Dec 1 to Dec 2
$586
includes taxes & fees
Dec 1 - Dec 2
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Langham, Chicago
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Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $436 per night from Dec 15 to Dec 16
$436
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Waldorf Astoria Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $369 per night from Dec 15 to Dec 16
$369
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Nobu Hotel Chicago
Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $487 per night from Dec 17 to Dec 18
$487
includes taxes & fees
Dec 17 - Dec 18
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Four Seasons Hotel Chicago
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $484 per night from Dec 8 to Dec 9
$484
includes taxes & fees
Dec 8 - Dec 9
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Park Hyatt Chicago
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $453 per night from Dec 15 to Dec 16
$453
includes taxes & fees
Dec 15 - Dec 16
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Ritz-Carlton, Chicago
Four Seasons Hotel St Louis
5 out of 5
Fully refundable
  • 7 hours drive from Route 66 Raceway
The price is $491 per night from Nov 23 to Nov 24
$491
includes taxes & fees
Nov 23 - Nov 24
Stay at this 5-star luxury hotel in St. Louis. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff in our reviews. ...
Four Seasons Hotel St Louis
Rosewood Inn of the Anasazi
5 out of 5
Fully refundableReserve now, pay when you stay
  • 33 hours drive from Route 66 Raceway
The price is $559 per night from Nov 26 to Nov 27
$559
includes taxes & fees
Nov 26 - Nov 27
Book a stay at this business-friendly hotel in Santa Fe. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Rosewood Inn of the Anasazi
The St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Route 66 Raceway
The price is $545 per night from Dec 15 to Dec 16
$545
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The St. Regis Chicago
The Ritz-Carlton, St. Louis
5 out of 5
Fully refundableReserve now, pay when you stay
  • 7 hours drive from Route 66 Raceway
The price is $640 per night from Dec 8 to Dec 9
$640
includes taxes & fees
Dec 8 - Dec 9
Book a stay at this business-friendly hotel in St. Louis. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff ...
The Ritz-Carlton, St. Louis
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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.

5-Star Hotel in Historic Route 66

It’s time. No more meh motels and so-so stays. This vacation it’s all about living it up, and that starts with a great hotel. You want first-class service and award-winning restaurants. Well, let us introduce you to a 5-star hotel in Historic Route 66.

So nice you’ll blink twice

What makes a hotel worthy of supreme star-age? For starters, the service has to be top-notch and personalized. These hotels often have 24-hour room service, a welcome gift upon your arrival, and help you with your bags—even if you travel light.

Are they nicer? Heck yeah, they are! Most 5-star hotels have jaw-dropping aesthetics that give an authentic feel of class. And we’re not talking about that faux-gold soap dish your Aunt Tilda puts out for the guests—it’s the real deal.

Stars in your eyes

Are 5-stars hotels worth it? If you like the finer things in life, then yes, they sure are. But we also know you’re the type that likes to get your caviar on a fish stick budget. We’re right there with you, and that is why we make it easy to find the best 5-star hotel in Historic Route 66 for you. Sort by:

  • Price: Want to live large, but keep that budget balanced? We got you. We have 5-star hotels starting at $369.

  • Amenities: Historic Route 66 skyline view? Maybe a heated indoor pool? Looking for a Michelin-star restaurant? Search for the hotels that have the amenities you desire.

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book, and you might just save a ton.

When you’re looking for the top 5-star hotels in Historic Route 66—but don’t want to pay top dollar—let us help you out. You can get that posh palace of your dreams, and have money left to take on Historic Route 66 your way.