Historic Route 66 Beach Holidays

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    Save up to £750 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Top flight + Beach hotel deals in Historic Route 66

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

Kinzie Hotel

Downtown Chicago
£1,088
per person
26 Nov - 3 Dec
found 3 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,384
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,475
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,273
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,793
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 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
£1,793
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,525
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is located in a prime location with shops and restaurants nearby. The staff was very accommodating and helpful.

Reviewed on 15 Sept 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
£2,091
per person
1 Nov - 5 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Very nice hotel With beautiful rooms

Reviewed on 14 Sept 2026

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3 Night Beach holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£989
per person
1 Dec - 4 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Awesome

Reviewed on 15 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£996
per person
1 Dec - 4 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,208
per person
1 Dec - 4 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
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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
£1,120
per person
1 Nov - 5 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£2,409
per person
12 Nov - 16 Nov
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,250
per person
12 Nov - 16 Nov
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
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Find your perfect Historic Route 66 beach holiday

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

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Historic Route 66 beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in Historic Route 66?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Historic Route 66 beach holidays, which start from £989. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in Historic Route 66?

Enjoy out-of-season seclusion on a beach holiday to Historic Route 66 during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in Historic Route 66 with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a Historic Route 66 beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute Historic Route 66 beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in Historic Route 66. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find Historic Route 66 beach holidays which are all inclusive?

A beach holiday to Historic Route 66 is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a Historic Route 66 beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a Historic Route 66 beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Historic Route 66 on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.