San Juan
Chicago → San Juan
$217 USDRoundtrip
✓ $191.04 USD−$25.96 · checked 18 days ago
Nov 2 – Nov 6, 2026 · United Airlines · Nonstop
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← Chicago Deals / Caribbean
Cheap Flights From Chicago to Caribbean
Active Caribbean deals departing Chicago.
Punta Cana
Chicago → Punta Cana
$393 USDRoundtrip
✓ $359.57 USD−$33.43 · checked 18 days ago
Nov 13 – Nov 20, 2026
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Nassau
Chicago → Nassau
$357 USD
$442 USD+$85 · checked 18 days ago
Nov 6 – Nov 12, 2026
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Other regions from Chicago