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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    £635pp
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    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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    £1840pp
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    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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    £720pp

    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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    £895pp

    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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    £836pp

    Chicago, Boston & Washington DC

    Visit three of America’s most famous cities on this incredible holiday to East Coast USA.
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    £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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    £897pp
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    OFFER

    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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    £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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    £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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    £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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