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
    £836pp

    Mile After Magnificent Mile: A Taste of Route 66 Fly Drive

    Travel through the state of Illinois getting a taste of Route 66 and experience mile after magnificent mile.
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    £735pp

    Boston & Chicago

    Visit two of America’s most famous cities on this incredible holiday to East Coast USA.
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    £848pp

    Chicago Weekender

    3 Nights in The Windy City
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    £1673pp

    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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    £999pp

    New York & Chicago

    Immerse yourself in both of these vibrant cities, from the five boroughs head in The Windy City or visit the Brooklyn...
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    £2084pp

    Heart of the Nation – 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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    £799pp

    Las Vegas & Chicago

    A popular twin city trip combining the East Coast's windy city and the hot desert in Vegas
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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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    £3097pp

    Historic Route 66 Adventure

    Immortalized in folklore, film and song, Route 66 remains the iconic symbol of the great American road trip
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    £2755pp

    Route 66 by Rail

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