Compare Chicago to Cuba flight deals starting at $248

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Find flights from Chicago (ORD) to Cuba

Chicago (ORD) to Havana (HAV)

Depart Fri 12 Oct 2018,
Return Sat 27 Oct 2018
from$ 248*Viewed: 3 minutes 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.
Stone road lined by colorful houses in Cuba

Plan ahead for flights from Chicago to Cuba

from
to
Type
Dates
Price*
Chicago (ORD)
to Havana (HAV)
Roundtrip
Depart Tue 16 Oct 2018
Return Wed 31 Oct 2018
from$ 248*Viewed: 3 minutes 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.