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Find cheap one-way flights from Chicago to Havana starting at US$1,308.

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to book flights from Chicago to Havana?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Cheapest airlines flights from Chicago to Havana

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Copa Airlines
From US$1,308
ANA airlines

Find more flights and airlines

Find cheap flights from Chicago to Havana by different airports

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Havana.

  • Cheapest
    Copa Airlines
    ORD
    07:53
    16h 28m
    1 transfer
    HAV
    01:21
    O'Hare International Airport - Jose Marti International Airport
    Tue, Apr 9Copa Airlines
    US$1,308
  • Copa Airlines
    ORD
    07:53
    16h 28m
    1 transfer
    HAV
    01:21
    O'Hare International Airport - Jose Marti International Airport
    Tue, Apr 9Copa Airlines
    US$1,308
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Havana (HAV) the cheapest?

    Airlines adjust prices for flights from Chicago to Havana based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Chicago (CHI) to Havana (HAV) cost?

    According to Trip.com's data, the lowest price is around $1,372.
  • What is the transportation method from the main airport to downtown in Havana?

    • The distance from Jose Marti International Airport to downtown is about 13km. It takes about 30 minutes by taxi.

Chicago to Havana Flight Information

Cheapest nonstop flight price

$1,307

Off-season for travel

December

Peak season for travel

April