Historic Route 66 Romantic Holidays
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Top Romantic holiday packages in Historic Route 66
- Swissotel - Chicago
27 Dec - 31 DecSwissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,584 reviews)"The Swisshotel was a last minute choice when the hotel where I was originally booked had some staffing issues. Swisshotel is a modern, well maintained property. I did have some issues with the wifi, but other than that the stay was good. Spacious room with good work areas."Reviewed November 13, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct£957£806found 11 hours agoper traveller - Trump International Hotel & Tower Chicago
27 Dec - 31 DecTrump International Hotel & Tower Chicago + Flight
Downtown Chicago4 nights5.0 star property9.6/10 - Exceptional (2,075 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct£1,543£1,215found 11 hours agoper traveller - The Peninsula Chicago
27 Dec - 31 DecThe Peninsula Chicago + Flight
Downtown Chicago4 nights5.0 star property9.8/10 - Exceptional (1,000 reviews)Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct£1,858£1,513found 11 hours agoper traveller - Pendry Chicago
27 Dec - 31 DecPendry Chicago + Flight
Downtown Chicago4 nights4.5 star property9.2/10 - Wonderful (1,164 reviews)"The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."Reviewed November 8, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct£1,085£886found 11 hours agoper traveller - L7 CHICAGO by LOTTE HOTELS
27 Dec - 31 DecL7 CHICAGO by LOTTE HOTELS + Flight
Downtown Chicago4 nights4.5 star property9.6/10 - Exceptional (5,240 reviews)"We chose a room with a river view. It was magnificent. The staff were pleasant and helpful enough. In particular the door person, Christy, was very friendly and helpful ( Thank you). Our room was clean and spacious and we really liked the big shower. We checked out the restaurant at the bar for happy hour which was quite good. They do give a discount for guests. If you go for breakfast, make sure you have a bit of extra time, as the kitchen was a bit slow and the bacon and potatoes were a..."Reviewed November 13, 2026Return • Dublin (DUB) - Chicago (ORD)DUB - ORD • Direct ORD - DUB • Direct£1,032£855found 11 hours agoper traveller
Top Romantic Historic Route 66 Hotels
Ramada by Wyndham Williams/Grand Canyon Area
Ramada by Wyndham Williams/Grand Canyon Area
Quality Inn Holbrook near Petrified Forest
Quality Inn Holbrook near Petrified Forest"Great room and close to the petrified forest. Everything you need when road tripping"
"We enjoyed our stay! The property was very clean and our room was nice! We would definitely recommend staying here! ❤️"
The L Motel - Downtown Flagstaff
The L Motel - Downtown Flagstaff
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood"The place was okay, but the room smelled strongly of urine (maybe a previous pet). It was more of a 6-7 star place. Not sure why so many websites had it as 8-9 stars."
Americas Best Value Inn & Suites Flagstaff
Americas Best Value Inn & Suites Flagstaff
Terrace #1 | 2 BR/1BA | Spend Spring in Flagstaff!
Terrace #1 | 2 BR/1BA | Spend Spring in Flagstaff!"This stay was AWESOME ! The beds were so comfortable, the home was immaculate.m and we felt so incredibly safe so close to Downtown. We had the pleasure of staying here with our puppy and the accessibility to the backyard was absolutely fantastic. Our stay was met with calm and serene every time we stepped foot in the door. Everything that we wanted to explore was walking distance. The host responded quickly with any questions we had. "
Terrace Main | 5BR/3BA | Spend Spring in Flagstaff!
Terrace Main | 5BR/3BA | Spend Spring in Flagstaff!"The house was ok. There was an issue with the outlets not working in one room, the dishwasher was not secured and would fall forward when the trays were pulled out, and one of the pans in the kitchen needs to be replaced. Other than that, it was fine."
How to find a romantic Historic Route 66 holiday
How can I find the best Historic Route 66 vacation packages for couples?
Use our easy-to-use holiday search tools to plan your most-romantic getaway to Historic Route 66. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.
Can I book cheap Historic Route 66 romantic holidays for two?
Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Historic Route 66 that start from £806. Prices and availability are subject to change. Additional terms may apply.
What should I think about when booking a Historic Route 66 romantic getaway?
The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.
What should I look for in a luxury romantic holiday to Historic Route 66?
Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.
Can I book a romantic hot-tub holiday in Historic Route 66?
What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.
How can I find romantic holidays for couples in Historic Route 66 that are all inclusive?
Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.
Can I book a romantic trip to Historic Route 66 with free cancellation and/or flexible dates?
Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.
Why should I book my Historic Route 66 romantic holiday with Expedia?
At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.