Compare Chicago to Dominican Republic flight deals starting at $397

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Find flights from Chicago (ORD) to Dominican Republic

Chicago (ORD) to Punta Cana (PUJ)

Depart Tue 13 Nov 2018,
Return Wed 28 Nov 2018
from$ 397*Viewed: 6 hours ago

Chicago (ORD) to Santo Domingo (SDQ)

Depart Mon 10 Dec 2018,
Return Tue 25 Dec 2018
from$ 477*Viewed: 6 hours ago

Chicago (ORD) to Santiago de los Caballeros (STI)

Depart Wed 28 Nov 2018,
Return Thu 13 Dec 2018
from$ 443*Viewed: 6 hours ago

Chicago (ORD) to Puerto Plata (POP)

Depart Fri 12 Oct 2018,
Return Sat 27 Oct 2018
from$ 525*Viewed: 6 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.
Wooden hut, small boats and rocks by the beach in Dominican Republic

Plan ahead for flights from Chicago to Dominican Republic

from
to
Type
Dates
Price*
Chicago (ORD)
to Punta Cana (PUJ)
Roundtrip
Depart Tue 13 Nov 2018
Return Wed 28 Nov 2018
from$ 397*Viewed: 6 hours ago
Chicago (ORD)
to Santiago de los Caballeros (STI)
Roundtrip
Depart Wed 28 Nov 2018
Return Thu 13 Dec 2018
from$ 443*Viewed: 6 hours ago
Chicago (ORD)
to Santo Domingo (SDQ)
Roundtrip
Depart Mon 10 Dec 2018
Return Tue 25 Dec 2018
from$ 477*Viewed: 6 hours ago
Chicago (ORD)
to Puerto Plata (POP)
Roundtrip
Depart Fri 19 Oct 2018
Return Sat 3 Nov 2018
from$ 525*Viewed: 6 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.