Upvote:1
There still are no direct flights from the USA to Cuba. While diplomatic relations on an upswing, US carriers still don't serve the island. You would have to route yourselves via Mexico, Panama, Grand Caymans, Bahamas, etc.
As you are coming via the west coast and she is coming from the east, it would be less flying if she went via a Caribbean nation and you went via Mexico, then try to coordinate flight times to arrive in Havana close to the same time.
If you want to enter Cuba as a couple, then it might be most economical for her to come to you, meeting in Mexico City, as there are often pretty good vacation fares to Mexico from various US gateways.
Upvote:2
You can fly via Mexico City, a simple momondo search shows that you can buy one way tickets for 385 USD or return tickets for 611 USD on some random dates that I tried, take your time and find the most suitable connections for yourself.