Holiday Deals Chicago

If you’re a first-time visitor or a seasoned Chicagoan, the city skyline never ceases to impress. Our advice is to go between May and September. That’s when the city comes alive with outdoor food and music festivals.

Holiday Deals

If you can dream it, we can make it happen...
  • From
    £789pp

    Chicago – Spring 2022

    Chicago is a city steeped in some of America’s richest history and yet it maintains a lively, energetic atmosphere ...
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  • From
    £2299pp
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    OFFER

    Heart & Soul of America – Route 66 Fly Drive

    A road trip across America is something that most people long to do and with this Drive America option you can drive ...
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    £1829pp
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    OFFER

    Historic Route 66 Fly Drive

    Get your kicks along America’s mother road and most historic highway, Route 66! Stroll through quaint small towns o...
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    £729pp
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    OFFER

    Chicago & Washington DC

    Washington is a city of history but it also buzzes with lively cafes and restaurants, great shopping and lots of fun ...
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    £3973pp

    Classic Route 66 Escorted Tour

    Explore historic Route 66, taking in Chicago, the Old West in Oklahoma or kick up your heels in Albuquerque.
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  • From
    £2775pp

    Route 66 by Rail

    Board Amtrak® and ride the rails along historic Route 66!
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    £2040pp

    California Coast by Rail

    Travel down the gorgeous California Coast as you venture from San Francisco to San Diego, with stops in Paso Robles a...
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