Cheapest trips from Chicago

Walled colonial city on the Caribbean with colourful balconies, salsa rhythms, and the Rosario Islands offshore.

The Big Easy — French Quarter jazz, Creole cuisine, voodoo history, and nonstop festival energy.

Jamaica's resort coast with jerk-chicken shacks, Dunn's River Falls, reggae beats, and Blue Mountain coffee.

High-altitude capital with a thriving food revolution, street art, and the Gold Museum.

Keep Portland Weird — food-cart pods, Powell’s Books, craft coffee, and Mount Hood on the horizon.

Metroplex hub with the JFK memorial, Fort Worth stockyards, and Texas-sized BBQ and Tex-Mex culture.

Live Music Capital of the World with BBQ trails, bat bridges, and a tech-fueled creative energy.

Massive capital with world-class museums, ancient Aztec ruins, incredible tacos, and vibrant neighborhoods.

All-inclusive Caribbean paradise with palm-fringed beaches, golf courses, and Saona Island day trips.

Banking hub with NASCAR speedways, whitewater rafting in the city centre, and a booming brewery district.