Explore top 2026 5 Star Hotels in Historic Route 66

Name: The St. Regis Chicago
Price range: $555 total
Rating: 9

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Top Historic Route 66 5 Star hotels

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$420 nightly

$493 total

Jan 11 - Jan 12, 2026

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 ...

9.2/10 Wonderful! (1,000 reviews)

This is a tough one as we enjoyed the property and staff but it did not live up to a 4 or higher star rating hotel - staff did not change feather pillows and sheets until day #2 as we requested in advance and, of course, we had allergic reactions, they did apologize, but considering their rates and ...

Reviewed on Dec 24, 2025

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$426 nightly

$500 total

Jan 25 - Jan 26, 2026

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, ...

9.6/10 Exceptional! (1,001 reviews)

The hotel is beautiful and the staff welcoming us was top notch. The reason I knocked off a star is because we picked the double bed option. I did not read the fine print and was expecting two queen beds instead of two full beds. We did not get much sleep both nights due to the lack of space in the ...

Reviewed on Dec 23, 2025

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$475 nightly

$558 total

Jan 4 - Jan 5, 2026

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. ...

9.6/10 Exceptional! (1,000 reviews)

Our stay

Reviewed on Dec 22, 2025

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$319 nightly

$374 total

Jan 4 - Jan 5, 2026

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 ...

9.4/10 Exceptional! (1,810 reviews)

Check in was smooth. Each Trump team member was welcoming, knowledgeable and efficient. My room was upgraded on a complementary basis. The room was well equipped, large, had a great view of the city and was clean and comfortable. The fitness center was was exceptionally equipped and spacious.The ...

Reviewed on Dec 28, 2025

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$356 nightly

$418 total

Jan 4 - Jan 5, 2026

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 ...

9.2/10 Wonderful! (1,003 reviews)

Super comfortable bed, and the deep bathtub alone is worth the stay!

Reviewed on Dec 26, 2025

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$387 nightly

$454 total

Jan 1 - Jan 2, 2026

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, ...

9.4/10 Exceptional! (999 reviews)

Great

Reviewed on Dec 17, 2025

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$319 nightly

$374 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...

9.2/10 Wonderful! (764 reviews)

Well stock bar

Reviewed on Dec 23, 2025

Four Seasons Hotel St Louis

999 North Second Street St. Louis MO

Fully refundableReserve now, pay when you stay

$415 nightly

$485 total

Jan 1 - Jan 2, 2026

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! (1,001 reviews)

Didn’t have breakfast

Reviewed on Dec 23, 2025

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$371 nightly

$435 total

Jan 2 - Jan 3, 2026

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, ...

9/10 Wonderful! (1,002 reviews)

I have nothing but great things to say about my stay. I’ve stayed at another five-star hotel in the same area, and the level of service here far surpassed my previous experience. I would absolutely recommend this hotel.

Reviewed on Dec 27, 2025

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$473 nightly

$555 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...

9/10 Wonderful! (86 reviews)

All the anove

Reviewed on Dec 15, 2025

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Historic Route 66 Resorts & 5 Star Hotels

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 5-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.

Recent Historic Route 66 hotel reviews by fellow wanderers

Hilton Chicago/Magnificent Mile Suites

5 out of 5

Posted 19 hours ago

Travelocity Verified Review

"Easy check in and check out, staff were very friendly, room was great, bed was very comfortable. The hotel was also very clean. We loved the location. It was so close to Michigan Avenue, but it was quiet. "

A verified traveler stayed at Hilton Chicago/Magnificent Mile Suites