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...
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    €699pp
    HOT
    OFFER

    Christmas Shopping in Chicago

    Enjoy the magic of Christmas in the city of Chicago where you can enjoy Christmas markets, ice skating, fantastic sho...
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    €1995pp
    HOT
    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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    €792pp

    Chicago & Philadelphia

    Start your holiday to America in Chicago on the stunning shores of Lake Michigan before travelling to Philadelphia, k...
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    €979pp

    Chicago & New York

    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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    €919pp

    Chicago, Boston & Washington DC

    Visit three of America’s most famous cities on this incredible holiday to East Coast USA.
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    €945pp

    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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    €1013pp

    Chicago & Detroit: Singing the Best of the Blues & Motown!

    These 2 great cities are steeped in music heritage that you can still experience today.
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    €2355pp

    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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    €4369pp

    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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    €3562pp

    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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    €3115pp

    Route 66 by Rail

    Board Amtrak® and ride the rails along historic Route 66!
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    €2300pp

    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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