Romantic Vacations in Historic Route 66 2026

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Flight and Romantic hotel deals in Historic Route 66

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

Hotel 505 River North

Downtown Chicago

Save 100% on your flight

CA $1,216

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (2,924 reviews)

The property is in a great location. The rooms are ok nothing special. Needs better attention to cleanliness; I found hair in the bathroom. The restaurant is very poor; the menu is below average, and the buffet breakfast is worse than a free Holiday Inn breakfast, yet they still wanted to charge you $40 for it. If you arrive late, after 10 pm, you can not find food on the premises, not even room service. No restaurant on Sundays and Mondays. I would say the only good thing was location.

Reviewed on Oct 13, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

CA $1,699

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $2,787

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Great location

Reviewed on Oct 12, 2026

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

CA $1,230

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

8.6/10 Excellent! (2,274 reviews)

Great stay

Reviewed on Oct 13, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

CA $1,226

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

8.2/10 Very good! (3,105 reviews)

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5* Romantic holidays in Historic Route 66

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

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

Historic Eastside

CA $1,818

per person

Dec 6 - Dec 12

found 1 hour ago

Roundtrip non-stop flight included

Vancouver (YVR) to Albuquerque (ABQ)

8.2/10 Very good! (1,001 reviews)

This was our first time staying at La Posada de Santa Fe. The experience was nice. They had no heating or hot water due to a gas leak. However, the manager provided a discount and also a complimentary breakfast. The staff were friendly. The room was very cozy.

Reviewed on Oct 11, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $2,787

per person

Nov 17 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Great location

Reviewed on Oct 12, 2026

Rosewood Inn of the Anasazi

Downtown Santa Fe

CA $3,403

per person

Dec 14 - Dec 20

found 15 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Albuquerque (ABQ)

9.6/10 Exceptional! (918 reviews)

Arrived late. Staff offered to have a Caesar salad waiting for me in the fridge. And it was complimentary. Also brought me a pot of tea and cookies. All complimentary. Lovely room but chilly. They had the fireplace on before I came. Also, several snacks were in the room were, without charge, and they told me to take them home if I didn’t use them. Also, daily water - no charge. Restaurant food was very good with a nice variety. I only had breakfast there. Also, they will drive you anywhere, also complimentary. They picked me up at a store, drive me to UPS and waited for me and drove me to another store. Outstanding property and service. Location is in the middle of everything.

Reviewed on Oct 6, 2026

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3 Night Romantic holidays in Historic Route 66

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

The Talbott, Autograph Collection

Downtown Chicago

CA $1,093

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Only negative was light water pressure at the shower, everything else was top notch. Great location, large immaculate rooms, great beds and nice bar and breakfast.

Reviewed on Oct 13, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,385

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Great location

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,203

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

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4 Night Romantic holidays in Historic Route 66

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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

CA $1,164

per person

Dec 2 - Dec 6

found 19 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,822

per person

Nov 19 - Nov 23

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Great location

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

CA $1,233

per person

Nov 19 - Nov 23

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

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What are some of the benefits of booking a romantic Historic Route 66 vacation?

When booking a romantic Historic Route 66 vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in United States of America.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Historic Route 66 destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in Historic Route 66?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,093 and can enjoy savings of up to 28 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in Historic Route 66?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Historic Route 66 certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Historic Route 66.

Can I book a romantic Historic Route 66 vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Historic Route 66 search.

Can I book a romantic trip to Historic Route 66 that is fully refundable?

Several romantic Historic Route 66 vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.