Flights from Chicago to the Dominican Republic from $ 351*
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1 Passenger, Economy
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today
today
Find United's best fares from Chicago to the Dominican Republic
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Chicago (ORD)to
Punta Cana (PUJ)01/11/26 - 01/15/26from$Â 351Viewed: 4 hours agoRoundtripEconomy
Chicago (ORD)to
Santo Domingo (SDQ)02/24/26 - 03/03/26from$Â 390Viewed: 4 hours agoRoundtripEconomy
Chicago (ORD)to
Santiago de los Caballeros (STI)01/20/26 - 02/03/26from$Â 396Viewed: 4 hours agoRoundtripEconomy
Chicago (ORD)to
Puerto Plata (POP)01/22/26 - 01/26/26from$Â 388Viewed: 4 hours agoRoundtripEconomy
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.
Business class flights from Chicago to the Dominican Republic
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Chicago (ORD)to
Punta Cana (PUJ)
03/11/26 - 03/17/26
Roundtrip
Business
from
$Â 1,021
Viewed: 19 hours ago
Chicago (ORD)to
Santo Domingo (SDQ)
03/02/26 - 03/06/26
Roundtrip
Business
from
$Â 746
Viewed: 14 hours ago
Chicago (ORD)to
Santiago de los Caballeros (STI)
02/07/26 - 02/15/26
Roundtrip
Business
from
$Â 838
Viewed: 17 hours ago
Chicago (ORD)to
Puerto Plata (POP)
01/14/26 - 01/18/26
Roundtrip
Business
from
$Â 1,220
Viewed: 16 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.