Havana (HAV) → Chicago (ORD)

2,172 km
3h 13m flight
From $340
Chicago destination photo

About Havana to Chicago Flights

Discover the best flights from Havana to Chicago, covering 2,172 km in approximately 3h 13m. Havana (HAV) to Chicago (ORD) is one of the popular medium-haul routes connecting Cuba and United States. With 7 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Havana to Chicago.

12-Month Price History

Flight prices from Havana to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $481, while July sees the highest prices, averaging $816. Savvy travelers can save up to 41% by choosing their travel dates wisely.

Best Time to Fly

Cheapest Month

February

Save up to 40% on average

Most Expensive

July

Peak season pricing

Book in Advance

78 days

For best prices

Booking Tips

For the best prices on Havana to Chicago flights, we recommend booking 175 days in advance. International flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.

Airlines Serving This Route

United Airlines

UA

Economy

$760

Business

$3180

First

$4410

American Airlines

AA

Economy

$810

Business

$2930

First

$5650

Kalitta Air

K4

Economy

$840

Business

$3450

First

$4560

Delta Air Lines

DL

Economy

$880

Business

$3350

First

$4350

British Airways

BA

Economy

$940

Business

$3490

First

$5510

SkyWest Airlines

OO

Economy

$940

Business

$2970

First

$4420

Air France

AF

Economy

$1050

Business

$2920

First

$4920

Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.

Alternative Flight Options

Milwaukee destination photo

HavanaMilwaukee

José Martí International (HAV) to Milwaukee Mitchell International (MKE)

Distance: 2,276 km

Average price: $574

View this route →
Chicago destination photo

HavanaChicago

José Martí International (HAV) to Chicago Midway International (MDW)

Distance: 2,148 km

Average price: $549

View this route →

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Frequently Asked Questions

How long is the flight from Havana to Chicago?

The flight time from Havana (HAV) to Chicago (ORD) is approximately 3 hours and 13 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.

What is the distance between Havana and Chicago?

The aerial distance between Havana and Chicago is 2,172 kilometers (1,350 miles). This is the straight-line distance, which is used to calculate flight times.

Which airlines fly from Havana to Chicago?

Several airlines operate flights between Havana and Chicago, including American Airlines, United Airlines, SkyWest Airlines and 4 more airlines. Direct flights are available on this route.

What is the cheapest month to fly from Havana to Chicago?

Based on historical data, February typically offers the lowest airfares for flights from Havana to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.

How far in advance should I book my flight to Chicago?

For the best prices on Havana to Chicago flights, we recommend booking 64 days in advance. International flights generally require earlier booking than domestic routes.

Do I need a visa to travel from Havana to Chicago?

Visa requirements depend on your nationality and the purpose of your visit. Citizens of Cuba traveling to United States should check the latest visa requirements. Visit our partner site visarequirements.io for detailed visa information.

What is the time difference between Havana and Chicago?

Havana operates on America/Havana time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.