[Summer Flight Deal] $279: Chicago to Havana, Cuba (R/T)

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Cheap flights to Cuba from 60+ U.S. cities from $197 were recently featured on Thrifty Traveler Premium! Subscribe to Premium to get instant notification of cheap international flights from your city.


Cheap sale on Delta round-trip flights from Chicago to Havana, Cuba. Availability August – November. One short stop each way. Fare includes free carry-on and seat assignment. Book quick, this fare won’t last!

Thrifty Tip #1: Read our tips for traveling to Cuba in 2018. A visa must be purchased from Delta before your flight ($50-$100). You will need to qualify under one of the 12 categories of allowed travel. Per the new Trump era rules, you will want to avoid state-run restaurants and hotels: stay at Airbnb’s and eating at locally owned restaurants (they will be the top ones on TripAdvisor).

Thrifty Tip #2: Want more deals like this sent to your inbox? Become a Thrifty Traveler Premium subscriber and get instant flight deal notifications to international destinations!



Fare Availability:

Chicago to Havana, Cuba (ORD – HAV) – $279 round trip

  • Departures: August 7, 9, 14-15, 17, 20-22, 24, 27-29, Sept 2, 4-6, 8, 11-13, 15, 18-22, 24-26, Oct 1-3, 9-11, 15, 23, 27, 29-31, Nov 6-7, 10, 12-14, 19-20
  • Returns: August 13, 15-16, 20-26, 28-30, Sept 5-7, 10-15, 17-21, 23-29, Oct 2-3, 9, 11-12, 16-17, 24-26, Nov 5-7, 9, 11, 14-15, 28

How to Search & Book:

  • Book through Momondo – you will ultimately book directly through Delta

Hotel Accommodations:



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