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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    £3092pp
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    OFFER

    Historic Route 66 Escorted Tour

    Explore America's most iconic road trip, taking in Chicago, the Old West in Oklahoma or kick up your heels in Albuque...
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    £1297pp
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    OFFER

    Chicago & Washington DC

    From the world-class museums, amazing shopping and vibrant nightlife of Chicago to the history and iconic sights of W...
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    £4579pp

    Eagle Rider Route 66 Self Guided Motorcycle Tour

    A 15 day journey riding along the world famous “Mother Road” highway from Chicago to Los Angeles by motorcycle
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    £857pp

    Chicago for St Patrick’s Day

    The Windy City, a town situated on the shores of Lake Michigan famed for the iconic skyscrapers that dot the skyline...
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    £2345pp
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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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    £1619pp
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    Chicago & New York

    Chicago is a city steeped in some of America’s richest history and yet it maintains a lively, energetic atmosphere ...
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    £2800pp
    CRUISE

    Chicago, Fort Lauderdale Stay & Caribbean Cruise

    From the moment you board Celebrity Equinox for your next cruise, you’ll know: this ship is something special!
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