Find cheap flights from Chicago to Cuba

Find cheap flights from Chicago to Cuba

Search hundreds of travel sites at once for deals on flights to Cuba. Bundle your flight + hotel and save!

Round-trip
Economy
Chicago (CHI)
Cuba
Mon 1/3
Mon 1/10
Any month
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Include hotels

Good to know

Low season

January

High season

December

Average price round-trip

$316

Good deal round-trip

$266

Good deal one-way

$161
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 1% increase in price.
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Cuba

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to Cuba is February.

FAQs - booking Cuba flights

How does KAYAK find such low prices on flights to Cuba?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Cuba?

What is the Hacker Fare option on flights to Cuba?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Cuba?

COVID-19 information

Safety measures for airlines flying from Chicago to Cuba

Airlines flying from Chicago to Cuba have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Cuba

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Cuba

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Cuba

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Cuba

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