Historic Route 66 Romantic Holidays 2026

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Top flight + Romantic hotel deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

AU$2,913

per person

7 Dec - 12 Dec

found 20 hours ago

Return flight included

Melbourne (MEL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on 28 Sept 2026

Swissotel - Chicago

Downtown Chicago

AU$3,043

per person

7 Dec - 12 Dec

found 20 hours ago

Return flight included

Melbourne (MEL) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Wonderful rooms and great views

Reviewed on 27 Sept 2026

The Talbott, Autograph Collection

Downtown Chicago

AU$3,013

per person

7 Dec - 12 Dec

found 20 hours ago

Return flight included

Melbourne (MEL) to Chicago (ORD)

9.4/10 Exceptional! (178 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

AU$2,953

per person

7 Dec - 12 Dec

found 20 hours ago

Return flight included

Melbourne (MEL) to Chicago (ORD)

8.6/10 Excellent! (1,011 reviews)

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

AU$3,180

per person

7 Dec - 12 Dec

found 20 hours ago

Return flight included

Melbourne (MEL) to Chicago (ORD)

9.4/10 Exceptional! (3,867 reviews)

Hotel was amazing with great views!

Reviewed on 27 Sept 2026

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5* Romantic holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

AU$1,983

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9.6/10 Exceptional! (2,025 reviews)

It was great great great !

Reviewed on 28 Sept 2026

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

AU$2,452

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

AU$2,772

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9.8/10 Exceptional! (1,010 reviews)

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4 Night Romantic holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

AU$828

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Reviewed on 28 Sept 2026

Swissotel - Chicago

Downtown Chicago

AU$921

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Wonderful rooms and great views

Reviewed on 27 Sept 2026

Level Chicago Fulton Market

Downtown Chicago

AU$888

per person

8 Dec - 12 Dec

found 21 hours ago

Return flight included

Phoenix (PHX) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

👍

Reviewed on 28 Sept 2026

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See all available trips from Columbus to Historic Route 66

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How can I book a romantic getaway in Historic Route 66?

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Plan your ultimate couple’s getaway in Historic Route 66 with our user-friendly search tools. Opt for a hotel suite with a view worth sharing on Instagram. Cruise with the top down and feel the warm breeze in your hair with a luxury car hire. Decide on a romantic couple’s spa treatment, a beachfront candle-lit dinner, or a glamorous night out on the town.

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How can I find great weekend couple’s holiday packages Historic Route 66?

Escape the weekly grind with fantastic couple’s weekend getaways in Historic Route 66. Enter your location and date preferences in your Expedia search and let us reveal hidden gems to leave you refreshed and love-struck for the week ahead.

Where can I find the most luxurious couple’s holiday packages in Historic Route 66?

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Why should book I my romantic Historic Route 66 holiday with Expedia?

Choose from our latest incredible deals or customise your trip in just a few clicks, with simple search and filter functions that make finding your next romantic Historic Route 66 getaway easy. Plus, booking a package with Expedia could save you money, too, making a Historic Route 66 holiday for couples all the more attractive.