A mural on a building with a man holding a machine and a sign that says "THIS LAND IS YOUR LAND".

Historic Route 66 Fishing Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Top Fishing holiday packages in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
  • 20 Jan - 24 Jan

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,007 reviews)
    "I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items."
    Reviewed November 9, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £898
    £720
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,081 reviews)
    "Very good service"
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,797
    £1,324
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - 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, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,091
    £819
    per traveller
    found 1 day ago
    Pendry Chicago
  • 11 Jan - 16 Jan

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,012 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • 1 stop
    £1,079
    £841
    per traveller
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • 20 Jan - 24 Jan

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,310 reviews)
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,202
    £956
    per traveller
    found 1 day ago
    Viceroy Chicago

Top Fishing Historic Route 66 Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Historic Route 66 travel package cost?

Be ready to book, because a getaway to Historic Route 66 starts from just £720. When you combine your hotels, flights and car rentals into a package, you'll enjoy the lowest prices.

If I'm not able to travel, can I cancel my Historic Route 66 travel package?

Don't worry if you're rethinking your Historic Route 66 travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We know life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

How do I get a cheap travel package to Historic Route 66?

Book everything in one place with our Historic Route 66 travel packages. We have incredible bargains on hotels, flights and more that'll keep your wallet happy and adventurous side satisfied. And, with more than 550 air carriers and 1,000,000 properties all over the world to select from, you'll have the flexibility to mix and match as you please.

Does Expedia offer Book Now, Pay Later Historic Route 66 holidays?

We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you want to grab an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you secure your getaway.

How far in advance should I book my Historic Route 66 holiday?

While prices do change, we generally advise reserving your seat as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If you're booking late, you may still get lucky. Cheaper tickets to Historic Route 66 sometimes emerge only weeks before departure.

What does an Expedia Historic Route 66 travel package include?

With Expedia, you can select a combination of hotels, flights and car rentals to build your perfect Historic Route 66 package. Once you've made your booking, you can add on fun stuff like tours and experiences. Remember — the more you bundle, the more deals you'll score!

What should I know before booking a Historic Route 66 travel package?

Locking in all the parts of your holiday together is a simple way to save. Combine your car rentals, flights and hotels into a neat little package. But it's not just hotels. Expedia features all sorts of properties, including holiday rentals such as beach villas and city residences. The list goes on!

Can I choose my airline with a Historic Route 66 Expedia travel package?

You can, and with over 550 airlines to choose from around the world, you're spoiled for choice. Have a look through the available options and find out which airline best fits your needs and budget.