Cheap flights from Chicago to Havana

Find cheap Havana to Chicago flights with our free search service. Compare all available fares for direct or connection flights from Havana to Chicago.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Chicago to Havana flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Chicago (CHI) - Havana (HAV) 2026-11-16 2026-11-25 717 USD 25 hours 20 minutes Connection 2026-11-12T15:22:05
Chicago (CHI) - Havana (HAV) 2026-12-31 2027-01-11 794 USD 29 hours 36 minutes Connection 2026-11-12T00:38:59
Chicago (CHI) - Havana (HAV) 2026-12-30 2027-01-10 884 USD 33 hours 29 minutes Connection 2026-11-12T00:39:09
Chicago (CHI) - Havana (HAV) 2026-12-27 2027-01-08 1045 USD 41 hours 36 minutes Connection 2026-11-12T00:21:44
Chicago (CHI) - Havana (HAV) 2026-12-22 2027-01-04 1439 USD 21 hours 4 minutes Connection 2026-11-11T23:46:27

Chicago to Havana flight status

Flight Origin Destination Departure Arrival Equip