Explore top 2026 5 Star Hotels in Historic Route 66

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Top Historic Route 66 5 Star hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$469 nightly
The price is $557 total per night from Jun 21 to Jun 22
$557 total
Jun 21 - Jun 22
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...
9.6/10 Exceptional! (1,893 reviews)
"Perfect!"

Reviewed on Jun 12, 2026

Opens in a new windowTrump International Hotel & Tower Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place Chicago IL
Fully refundableReserve now, pay when you stay
$505 nightly
The price is $600 total per night from Jun 28 to Jun 29
$600 total
Jun 28 - Jun 29
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (1,004 reviews)
"We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special"

Reviewed on Jun 1, 2026

Opens in a new windowFour Seasons Hotel Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$531 nightly
The price is $631 total per night from Jun 28 to Jun 29
$631 total
Jun 28 - Jun 29
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.8/10 Exceptional! (1,010 reviews)
"Very good hotel"

Reviewed on Jun 11, 2026

Opens in a new windowThe Langham, Chicago
La Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott

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

5 out of 5
330 E Palace Ave Santa Fe NM
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $298 total per night from Jun 14 to Jun 15
$298 total
Jun 14 - Jun 15
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
8.2/10 Very Good! (1,002 reviews)
"Nothing to criticize. All went well. In-house breakfast was as good as could be. Shuttle to near-by attractions was a plus. And the look of the place was in keeping with the architecture of the whole town. A lovely place, overall."

Reviewed on Jun 2, 2026

Opens in a new windowLa Posada de Santa Fe, A Tribute Portfolio Resort & Spa by Marriott
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$575 nightly
The price is $684 total per night from Jun 28 to Jun 29
$684 total
Jun 28 - Jun 29
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...
9.8/10 Exceptional! (1,007 reviews)
"We had a wonderful stay! It was absolutely beautiful and the service was top notch! We have a new favorite place to stay in Chicago! 😍"

Reviewed on Jun 9, 2026

Opens in a new windowThe Peninsula Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$513 nightly
The price is $609 total per night from Jul 5 to Jul 6
$609 total
Jul 5 - Jul 6
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...
9.4/10 Exceptional! (1,006 reviews)
"The staff was exceptional…going the extra mile at every opportunity."

Reviewed on Jun 12, 2026

Opens in a new windowWaldorf Astoria Chicago
The Ritz-Carlton, St. Louis

The Ritz-Carlton, St. Louis

5 out of 5
100 Carondelet Plaza St. Louis MO
Fully refundableReserve now, pay when you stay
$499 nightly
The price is $583 total per night from Jun 13 to Jun 14
$583 total
Jun 13 - Jun 14
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business ...
9.2/10 Wonderful! (570 reviews)
"We went on Memorial Day weekend which may have been why but there were so many weddings! (7) The car park was situated so that unless you walked outside and hiked the perimeter of the property you had to navigate through wedding guests to get to your car."

Reviewed on Jun 5, 2026

Opens in a new windowThe Ritz-Carlton, St. Louis
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$446 nightly
The price is $531 total per night from Jun 28 to Jun 29
$531 total
Jun 28 - Jun 29
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
9.2/10 Wonderful! (1,000 reviews)
"best service. nicest people. great room. excellent restaurants. its the Ritz and lived up to its reputation."

Reviewed on May 26, 2026

Opens in a new windowThe Ritz-Carlton, Chicago
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$494 nightly
The price is $587 total per night from Jun 28 to Jun 29
$587 total
Jun 28 - Jun 29
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.6/10 Exceptional! (1,003 reviews)
"The entire experience was incredible! The only place I will stay at while in Chicago from now on!"

Reviewed on Jun 10, 2026

Opens in a new windowPark Hyatt Chicago
Four Seasons Hotel St Louis

Four Seasons Hotel St Louis

5 out of 5
999 North Second Street St. Louis MO
Fully refundableReserve now, pay when you stay
$355 nightly
The price is $415 total per night from Jun 14 to Jun 15
$415 total
Jun 14 - Jun 15
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate kid-friendly dining and in-room childcare. ...
9.4/10 Exceptional! (1,007 reviews)
"Property great. They deliver excellent service at a great value without being intrusive. Food at Gordon Ramsay’s kitchen was exceptional and the ambiance was wonderful"

Reviewed on May 25, 2026

Opens in a new windowFour Seasons Hotel St Louis
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Five Star Hotels in Historic Route 66

Looking for your own little slice of heaven during your next trip? Check out all the best 5 star hotels in Historic Route 66 to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the five star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Historic Route 66 5 star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5 star hotels in Historic Route 66 before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

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