Historic Route 66 Beach Vacations

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Flight and Beach hotel deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
CA $745
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,128 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $915
per person
Nov 19 - Nov 23
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great! But parking was bad.

Reviewed on Aug 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,615
per person
Nov 17 - Nov 21
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,069
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.

Reviewed on Aug 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
CA $1,572
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
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5* Beach holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,615
per person
Nov 17 - Nov 21
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,387
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!

Reviewed on Aug 25, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,076
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Beach holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,069
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.

Reviewed on Aug 26, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,950
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,623
per person
Nov 6 - Nov 9
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

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See all available trips from Columbus to Historic Route 66
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4 Night Beach holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,216
per person
Sep 30 - Oct 4
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great! But parking was bad.

Reviewed on Aug 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,473
per person
Sep 30 - Oct 4
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.

Reviewed on Aug 26, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,784
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
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Find the best beach vacations in Historic Route 66

What are some benefits when booking beach vacations in Historic Route 66?

When you travel to the beach in Historic Route 66, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Historic Route 66?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Historic Route 66 trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Historic Route 66?

There are quite a few things you can do to get cheap beach vacations in Historic Route 66. Prices range from CA $745, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Historic Route 66. These package deals let you save by booking your accommodation and your flight together with savings of up to 25.

Why should I book family beach vacations?

When you're travelling with the family to Historic Route 66, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Historic Route 66?

It's easy to find a beachfront vacation accommodation in Historic Route 66 using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Historic Route 66 as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Historic Route 66 is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout United States of America. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.