Cheap Flights from Chicago to Havana
Find flight deals from Chicago to Havana
Compare prices, find the best time to fly, and save money.
Round-trip from
$569
American Airlines
2 stops
Chicago to Havana
One-way from
$356
United Airlines
Nonstop
Chicago to Havana
Popular in
December
Highest demand for flights based on searches. Prices may increase by up to 15%.
Cheapest in
Oct
Lowest prices on average. 15% potential savings. best time to book.
What is the cheapest month to fly?
Currently, Oct is the cheapest month to book a flight from Chicago to Havana. Prices can fluctuate, so booking in advance is recommended.
What is the cheapest day to fly?
Travelers seeking maximum savings should consider departing on weekdays. Monday often offers the lowest fares.
Best time of day to fly?
Flying early in the morning can often save you money compared to midday flights.
Flight Schedule: Chicago to Havana
| Airline | Departure | Arrival | Duration |
|---|---|---|---|
| American Airlines | 08:00 AM | 01:30 PM | 4h 00m |
| United Airlines | 02:15 PM | 07:45 PM | 4h 30m |
| Delta Air Lines | 10:30 PM | 03:00 AM (+1) | 5h 00m |
Stopover Options
Cheapest Stopover
Muscat (MCT)
Flights with a stop here start from $320.
Most Popular Stopover
Bahrain (BAH)
Travelers often choose to connect through Bahrain (BAH).
Airlines Flying This Route
Return Flight: Havana to Chicago
Planning your return trip? Flights from Havana to Chicago are also available with competitive pricing. It's often cheaper to book a round-trip ticket, but if you need flexibility, one-way fares are a great option.
Havana to Chicago FlightsFrequently Asked Questions
How long is the flight from Chicago to Havana?
The average flight time is approximately 3h 51 m, though this varies based on wind speeds and the specific flight path utilized by the airline.
What is the best price for this route?
Our data shows that Oct is typically the cheapest month to fly this route, with prices starting from $356. Booking 30-60 days in advance often yields the best savings.
Are there direct flights available?
Yes, there are typically direct flights available for this route daily. However, connecting flights with stops in major hubs like Dubai or Doha may sometimes offer better value.
What are the baggage allowance policies?
Most international airlines on this route offer 23-30kg of checked baggage for Economy class. Low-cost carriers may charge extra for checked bags, so always verify before booking.
Do I need a visa for travel?
Visa requirements depend on your nationality. Travelers should check with the embassy of Havana for specific entry requirements before their trip.
What time of day is cheapest to fly?
Early morning flights (before 8 AM) are often less expensive than flights during peak daytime hours. Red-eye flights can also offer significant discounts.
Can I cancel or change my flight?
Cancellation policies vary by airline and ticket class. Basic Economy tickets are often non-refundable, while Standard or Flex tickets allow changes for a fee. Check the specific fare rules during checkout.
Trending from UAE
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