Cheap Flights from Chicago to Caribbean

Chicago to Caribbean Flights

Fly to Caribbean from Chicago and save! We specialize in finding every airfare and timetable option on all flights to and from Canada on every airline in the world. Search now to find the cheapest flights from Chicago to Caribbean.

Tired of searching dozens of travel sites in your hunt for a great deal? You come to the right place. You won’t find a better price to Caribbean anywhere else online.

Routes to Countries in Caribbean

• Chicago to Dominican Republic
• Chicago to Puerto Rico
• Chicago to US Virgin Islands
• Chicago to St Maarten
• Chicago to Aruba
• Chicago to Haiti
• Chicago to Jamaica
• Chicago to Grenada
• Chicago to Trinidad and Tobago

• Chicago to Bahamas
• Chicago to Cayman Islands
• Chicago to Barbados
• Chicago to British Virgin Islands
• Chicago to Antigua and Barbuda
• Chicago to Turks and Caicos
• Chicago to St Lucia
• Chicago to Curacao
• Chicago to St. Kitts And Nevis

• Chicago to Martinique
• Chicago to Bonaire
• Chicago to Dominica
• Chicago to Guadeloupe
• Chicago to Anguilla
• Chicago to Saint Vincent and the Grenadines
• Chicago to Netherlands Antilles
• Chicago to Cuba
• Chicago to Montserrat

Route Info

AVG FLIGHT TIME:

Top Routes to Caribbean From Chicago

• Chicago to Punta Cana
• Chicago to Aguadilla
• Chicago to San Juan
• Chicago to Montego Bay
• Chicago to Santo Domingo
• Chicago to Port of Spain
• Chicago to Nassau
• Chicago to Grand Cayman
• Chicago to Bridgetown
• Chicago to Beef Island

• Chicago to Tortola
• Chicago to Antigua
• Chicago to Providenciales
• Chicago to Willemstad
• Chicago to Puerto Plata
• Chicago to Treasure Cay
• Chicago to Negril
• Chicago to Ocho Rios
• Chicago to Bimini
• Chicago to Virgin Gorda

• Chicago to Cayman Brac
• Chicago to Saba
• Chicago to Grand Turk
• Chicago to St. Thomas
• Chicago to Cayo Coco
• Chicago to Havana
• Chicago to Holguin
• Chicago to Santiago De Cuba
• Chicago to Varadero
• Chicago to Vieques