Departing from Chicago
Best Deals from Chicago
We scan 50+ destinations from O'Hare Intl (ORD) every 6 hours and surface the best all-in trips — flights, hotel, food, and activities.
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All-in price per trip, including flights from Chicago.
Popular destinations from Chicago
Click any destination to see budget details, best time to visit, and what it costs.
Cancún
Mexico
Caribbean CoastPrice from ORD →
Montego Bay
Jamaica
CaribbeanPrice from ORD →
Nassau
Bahamas
CaribbeanPrice from ORD →
Hamilton
Bermuda
AtlanticPrice from ORD →
San Juan
Puerto Rico
CaribbeanPrice from ORD →
Punta Cana
Dominican Republic
CaribbeanPrice from ORD →
Liberia
Costa Rica
GuanacastePrice from ORD →
San José
Costa Rica
Central ValleyPrice from ORD →
Grand Cayman
Cayman Islands
CaribbeanPrice from ORD →
Oranjestad
Aruba
CaribbeanPrice from ORD →
St. Maarten
Sint Maarten
CaribbeanPrice from ORD →
New York
USA
NortheastPrice from ORD →
All 38 destinations from Chicago
Browse every destination we track, with budget estimates and flight search.