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
    £579pp

    Chicago for St. Patrick’s Day

    Spend St. Patricks Day in The Windy City
    • More Detail
  • From
    £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...
    • More Detail
  • From
    £919pp

    Chicago, Boston & New York

    Visit three of America’s most famous cities on this incredible holiday to East Coast USA.
    • More Detail
  • From
    £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...
    • More Detail
  • From
    £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 ...
    • More Detail
  • From
    £869pp

    New York, Chicago & Las Vegas

    Three Cities...The Windy City...The City That Never Sleeps...Sin City
    • More Detail
  • From
    £799pp

    Las Vegas & Chicago

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

    Historic Route 66 Adventure

    Immortalized in folklore, film and song, Route 66 remains the iconic symbol of the great American road trip
    • More Detail
  • From
    £2267pp

    Route 66 by Rail

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