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Compare on trivago ↗Chicago packages ↗CHICAGO → CARIBBEAN · WINTER 2026–27
More beach days.
Less guesswork.
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2 adults + 3 childrenORD / MDWBeach · Food · Warm pools
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Flight leads
Indicative airfare data from Skyscanner. Four-seat estimates multiply a single-traveler fare; availability, infant charges, baggage and seats remain unverified.
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Royal Caribbean & more
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Vacations To Go ↗Royal Caribbean ↗Start with the break
Dec 18–28: 10 nights, no school missed with departure after 11 a.m. dismissal.
Dec 16–23: 7 nights, two full days and one half-day missed.
Jan 15–23: 8 nights, four full days missed with departure after dismissal.