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...
  • Chicago Summer
    From
    £839pp
    HOT
    OFFER

    Chicago Summer

    You'll be spilt for choice of things to do in this fantastic city. Enjoy 4 nights on this Chicago City Break.
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  • Chicago Direct
    From
    £857pp

    Chicago Direct

    Explore Chicago's iconic architecture and vibrant culture in a city known for its innovation.
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  • Historic Route 66 Escorted Tour
    From
    £3295pp
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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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  • Chicago & Washington, DC
    From
    £1339pp
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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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  • Eagle Rider Route 66 Self Guided Motorcycle Tour
    From
    £5295pp

    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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  • Historic Route 66 Fly Drive
    From
    £2659pp
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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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  • Chicago & New York
    From
    £1139pp
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    OFFER

    Chicago & New York

    Chicago and New York City, with rich histories and vibrant atmospheres, attract global visitors seeking dynamic urban...
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