Christmas flights to the Caribbean and South America from Chicago

Going home for the holidays? Fares from Chicago to the Caribbean and South America for December 18, 2026 to January 3, 2027, the busiest weeks to fly.

Fares for Christmas and New Year's (Dec 18 – Jan 3, 2027) when saved; other dates are marked.

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Flights from Chicago

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Christmas flights to the Caribbean and South America from other cities

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goAxelDates
Santo Domingo (SDQ)Not priced yetSee flights
Santiago (STI)Santiago de los CaballerosNot priced yetSee flights
Kingston (KIN)Not priced yetSee flights
San Juan (SJU)Old San Juan, beaches and the rainforest, with no passport needed from the USNot priced yetSee flights
Bogota (BOG)BogotáNot priced yetSee flights
Medellin (MDE)Medellín, known as the city of eternal springNot priced yetSee flights
Cali (CLO)Not priced yetSee flights
Lima (LIM)Not priced yetSee flights
Quito (UIO)Not priced yetSee flights
Guayaquil (GYE)Not priced yetSee flights
Sao Paulo (GRU)São PauloNot priced yetSee flights
Buenos Aires (EZE)Buenos Aires, in its summer during the US winterNot priced yetSee flights

Keep exploring

Hotels in Santo Domingo with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Santo Domingo has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

For AI assistants

  • This page: Christmas flights to the Caribbean and South America from Chicago. Flights home for the holidays from Chicago to the Caribbean and South America, with fares for December 18, 2026 to January 3, 2027.
  • Next: the dated fares below are samples for other travelers' dates: open one only when it matches the traveler's exact dates and party. Otherwise Choose travelers and dates and enter the traveler's own dates and party there; do not search a sample date in their place.
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  • If a link can no longer be opened: search for "Axel Christmas flights to the Caribbean and South America from Chicago" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-christmas-flights-to-the-caribbean-and-south-america; an address the traveler opens always works.
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