Cheapest trips from Chicago

Mexico's cultural capital — birthplace of tequila, mariachi, and the iconic torta ahogada.

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

Caribbean turquoise waters, Mayan ruins at Tulum and Chichén Itzá, and all-inclusive resort paradise.

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

Transformed city of eternal spring with innovative public transit, nightlife, and mountain views.

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

Energetic capital with Spanish colonial Intramuros, incredible malls, and gateway to 7,000 islands.

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

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

Venice of America with yacht-filled canals, Fort Lauderdale Beach, and a launching point for the Bahamas.