Explore top 2026 5 Star Hotels in Historic Route 66

Name: The St. Regis Chicago
Price range: $524 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

$395 nightly

$464 total

Mar 15 - Mar 16

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! (998 reviews)

Wonderful!

Reviewed on Feb 9, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$431 nightly

$506 total

Mar 15 - Mar 16

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! (1,002 reviews)

Best service in Chicago — whether desk service, room service, etc. Stunning property. Amazing bathtubs.

Reviewed on Feb 12, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$525 nightly

$616 total

Feb 15 - Feb 16

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)

Nice upgrade and amazing service

Reviewed on Feb 9, 2026

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$319 nightly

$374 total

Feb 22 - Feb 23

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! (1,840 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$406 nightly

$476 total

Mar 15 - Mar 16

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! (1,002 reviews)

Staff was great. Mattress not so great but room was awesome & location was awesome

Reviewed on Feb 8, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$395 nightly

$464 total

Feb 16 - Feb 17

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! (1,002 reviews)

All good

Reviewed on Feb 7, 2026

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$319 nightly

$374 total

Mar 8 - Mar 9

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! (788 reviews)

Everything was great about the property. Staff was super accomodating.

Reviewed on Jan 27, 2026

Four Seasons Hotel St Louis

999 North Second Street St. Louis MO

Fully refundableReserve now, pay when you stay

$415 nightly

$485 total

Feb 15 - Feb 16

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! (1,000 reviews)

Staff was extremely nice and room was great. Will definitely be staying here again.

Reviewed on Feb 1, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$396 nightly

$465 total

Mar 1 - Mar 2

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! (1,001 reviews)

The room was spotless, the staff was incredibly courteous. I don't want to say anywhere else in Chicago

Reviewed on Feb 7, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$446 nightly

$524 total

Feb 26 - Feb 27

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! (93 reviews)

The staff was exceptional, and the amenities, coupled with the stunning views of the river or city, make this a fantastic choice. The on-site restaurants provide convenient access to food. My only minor complaint is the absence of a mini fridge in the room to keep some drinks cool. I would definitely ...

Reviewed on Jan 12, 2026

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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.