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.
Saved round trips for Christmas and New Year's (Dec 18 – Jan 3, 2027).
Cheapest right now: San Juan $867 · Santo Domingo $1,369 · Medellin $1,454
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Christmas flights to the Caribbean and South America from other cities
Fares observed October 13 – 14, 2026. USD for the travelers shown. Search a trip for current prices.
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.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Santo Domingo (SDQ) | $1,369 (airline $1,441) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| Santiago (STI) | Santiago de los Caballeros | $1,526 (airline $1,607) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Kingston (KIN) | $1,651 (airline $1,738) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | $867 (airline $913) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Bogota (BOG) | Bogotá | $1,506 (airline $1,589) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Medellin (MDE) | Medellín, known as the city of eternal spring | $1,454 (airline $1,536) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Cali (CLO) | $1,808 (airline $1,913) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| Lima (LIM) | $2,234 (airline $2,364) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| Quito (UIO) | $1,849 (airline $1,957) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| Guayaquil (GYE) | $1,912 (airline $2,021) | Dec 18, 2026–Jan 3, 2027 | Check prices | |
| Sao Paulo (GRU) | São Paulo | from $1,944 (airline $2,046) | Dec 18, 2026–Jan 3, 2027 | Check prices |
| Buenos Aires (EZE) | Buenos Aires, in its summer during the US winter | $2,411 (airline $2,551) | Dec 18, 2026–Jan 3, 2027 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
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
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