Statistics on Chicago-Havana flights: what is the right price and when to buy your plane ticket?
Best time to go: what is the RIGHT price for a round-trip flight to Havana (from: Chicago)
The average price to go to Havana from Chicago airport is $ 631 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 503 (in february) and $ 802 (in december), which is a saving of $ 129 or a surplus of $ 171 (compared to the average price) depending on the period you leave.
The analysis of all prices reveals that the most frequent price is between $385 to $440 and it is generally more economical to leave on a wednesday and return on a wednesday on a flight with 1 or more layovers.
Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Havana before booking your flight.
If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Havana plane ticket.
How are these data calculated?
We have studied a sample of 22302 airfare prices from previous years for flights to Havana from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.
Average price depending on the departure month
Data analysis:
By leaving in february, the price of the plane ticket will statistically be the cheapest ($ 503, saving $ 129 compared to the average price over the year which is $ 631). Conversely, december will be the most expensive ($ 802).
Flight Chicago-Havana: when is the best time to go for the best price?
| Month | Good price* | Average price | Our opinion |
|---|---|---|---|
| January | $ 446 | $ 546 | good price |
| February | $ 442 | $ 503 the cheapest | very good price |
| March | $ 513 | $ 610 | fair price |
| April | $ 444 | $ 563 | good price |
| May | $ 430 | $ 533 | good price |
| June | $ 485 | $ 615 | fair price |
| July | $ 493 | $ 648 | fair price |
| August | $ 490 | $ 769 | high price |
| September | $ 428 | $ 650 | fair price |
| October | $ 425 | $ 625 | fair price |
| November | $ 495 | $ 703 | fair price |
| December | $ 559 | $ 802 the most expensive | very high price |
*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!
Price breakdown to travel from Chicago to Havana
Data analysis:
The prices for flights from Chicago to Havana range from $275 to $1264. 2% of tickets were purchased at the minimum price (from $275 to $330), 1% at the maximum price (from $1209 to $1264). The majority of plane tickets were purchased in the range of $440 to $495 (15% of tickets).
Cheapest airlines for the Chicago->Havana flight
There are 7 companies that serve Chicago from Havana airport: Copa, Viva Aerobus, United, American Airlines, Aeromexico (aerm), Southwest Airlines and jetBlue.
Data analysis:
Of the 22302 flights analyzed in previous years, Copa was the airline that offered the best fare most often in the flight ticket search results (37% of the time) on the Chicago->Havana route.
Which day of the week to leave?
Data analysis:
Statistically, Chicago-Havana flights departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday as your departure date, you can save an average of $63. On the other hand, departing on a sunday may cost you an additional $26.
Which day of the week to come back?
Data analysis:
Statistically, return flights from Havana to Chicago departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday for your return date, you will save an average of $35. Conversely, departing from Havana on a sunday may cost you an additional $40.
Top prices Chicago-Havana
| Round trip | Dates | Price | |
|---|---|---|---|
| Chicago → Havana | 03-05 to 08-05-2025 | $ 461 | layover flight with Copa |
| Chicago → Havana | 08-05 to 15-05-2025 | $ 460 | layover flight with Copa |
| Chicago → Havana | 12-05 to 19-05-2025 | $ 461 | layover flight with Copa |
| Chicago → Havana | 13-05 to 20-05-2025 | $ 460 | layover flight with Copa |
| Chicago → Havana | 15-05 to 22-05-2025 | $ 461 | layover flight with Copa |
| Chicago → Havana | 02-06 to 07-06-2025 | $ 459 | layover flight with Copa |
| Chicago → Havana | 04-06 to 09-06-2025 | $ 461 | layover flight with Copa |
| Chicago → Havana | 18-09 to 22-09-2025 | $ 459 | layover flight with Copa |
| Chicago → Havana | 06-10 to 12-10-2025 | $ 460 | layover flight with Copa |
| Chicago → Havana | 14-11 to 19-11-2025 | $ 431 | layover flight with Viva Aerobus |
When to book your flight Chicago - Havana to get the cheapest price?
Statistically, you will make the biggest savings by buying your plane ticket between 7 to 8 months in advance. However, you may end up paying a high price if you book between 4 to 5 months in advance.
Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Havana flight, it is recommended to book your ticket on a saturday.
How far in advance should I buy my flight?
Data analysis:
To get the cheapest flight ticket from Chicago to Havana, it is recommended to buy it 7 to 8 months before departure (it is then on average 552 $, which is a saving of 79 $ compared to the overall average price). On the other hand, if you buy your ticket 4 to 5 months in advance, you will pay the full price (90 $ more than the average price).
Depending on the departure month
The best time to buy your Chicago to Havana flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.
| Departure on... | How far in advance should I book? |
|---|---|
| January | Best time: 1 to 2 months before departure (average price: 495 $) Other interesting period(s): 2 to 3 months ($ 528), 3 to 4 months ($ 512) |
| February | Best time: 1 to 2 months before departure (average price: 461 $) Other interesting period(s): 2 to 3 months ($ 470), 5 to 6 months ($ 488) |
| March | Best time: 8 to 9 months before departure (average price: 570 $) Other interesting period(s): 1 to 2 months ($ 571), 2 to 3 months ($ 595), 3 to 4 months ($ 579), 7 to 8 months ($ 591) |
| April | Best time: 2 to 3 months before departure (average price: 494 $) Other interesting period(s): 1 to 2 months ($ 499), 3 to 4 months ($ 525), 4 to 5 months ($ 523) |
| May | Best time: 3 to 4 months before departure (average price: 451 $) Other interesting period(s): 1 to 2 months ($ 505), 2 to 3 months ($ 471), 4 to 5 months ($ 472) |
| June | Best time: 3 to 4 months before departure (average price: 539 $) Other interesting period(s): 1 to 2 months ($ 592), 2 to 3 months ($ 542), 4 to 5 months ($ 558), 5 to 6 months ($ 564) |
| July | Best time: 4 to 5 months before departure (average price: 527 $) Other interesting period(s): 1 to 2 months ($ 608), 2 to 3 months ($ 601), 3 to 4 months ($ 565), 5 to 6 months ($ 552) |
| August | Best time: 4 to 5 months before departure (average price: 480 $) Other interesting period(s): 2 to 3 months ($ 537), 3 to 4 months ($ 501), 5 to 6 months ($ 494), 6 to 7 months ($ 490) |
| September | Best time: 5 to 6 months before departure (average price: 415 $) Other interesting period(s): 3 to 4 months ($ 460), 4 to 5 months ($ 416), 6 to 7 months ($ 459) |
| October | Best time: 6 to 7 months before departure (average price: 412 $) Other interesting period(s): 1 to 2 months ($ 516), 4 to 5 months ($ 507), 5 to 6 months ($ 414) |
| November | Best time: 7 to 8 months before departure (average price: 519 $) Other interesting period(s): 0 to 1 month ($ 693), 1 to 2 months ($ 559), 2 to 3 months ($ 627), 5 to 6 months ($ 650), 6 to 7 months ($ 572), 8 to 9 months ($ 616) |
| December | Best time: 1 to 2 months before departure (average price: 673 $) Other interesting period(s): 0 to 1 month ($ 712), 2 to 3 months ($ 685), 6 to 7 months ($ 720) |
What day of the week should I book my flight ticket?
Data analysis:
Statistically, saturday is the day when plane tickets for Chicago->Havana are the cheapest. So, by buying your plane ticket on a saturday, you will save $9. Conversely, by buying it on a wednesday, you may end up paying $24 more.
Chicago to Havana: flight price when booking today
Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.
| Month | Current price | Our opinion | |
|---|---|---|---|
| April 2025 | $ 552 $507 to $631 | very good price | Find a flight |
| May 2025 | $ 471 $459 to $516 | very good price | Find a flight |
| June 2025 | $ 460 $459 to $461 | very good price | Find a flight |
| July 2025 | $ 473 $473 to $473 | very good price | Find a flight |
| August 2025 | $ 558 $515 to $601 | very good price | Find a flight |
| September 2025 | $ 459 $459 to $459 | very good price | Find a flight |
| October 2025 | $ 480 $460 to $498 | very good price | Find a flight |
| November 2025 | $ 517 $431 to $632 | very good price | Find a flight |
| December 2025 | $ 713 $713 to $713 | very good price | Find a flight |
| January 2026 | $ 546 $515 to $576 | fair price | Find a flight |
| February 2026 | $ 498 $498 to $498 | fair price | Find a flight |
Data analysis:
Compared to the average price, april, may, june, july, august, september, october, november and december are cheaper to travel to Havana. So it may be interesting to book now to leave during these months!