$1,434 Cheap Flights from Chicago (ORD) to Port-au-Prince (PAP)

View $1,434 flight on Tue, Sep 2, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.)

Cheap Flights from Chicago to Port-au-Prince (ORD-PAP)

Prices were available within the past 7 days and start at $1,434 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Chicago (ORD) to Port-au-Prince (PAP)
Origin airport
O'Hare Intl.
Destination airport
Toussaint Louverture Intl.
Distance
1858 mi

Chicago to Port-au-Prince Flights

The cheapest times to fly from Chicago to Port-au-Prince

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Port-au-Prince are during the month of . You can find some of the cheapest flights from Chicago to Port-au-Prince with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Port-au-Prince

Sunday is one of the best days to book for cheap flights from Chicago to Port-au-Prince: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Port-au-Prince

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Port-au-Prince in 2025. You can also book with separate airlines for your outbound and return journeys, from $1,434 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Port-au-Prince flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Port-au-Prince airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.) cost?
Discover the latest flight deals from ORD to PAP by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to PAP?
The cheapest flights from ORD to PAP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to PAP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ORD to PAP. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.)?
There are no daily nonstop flights available from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from ORD to PAP?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.) route, travel before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.) last-minute?
Booking your flight from ORD to PAP shortly before your getaway is generally more expensive. But if there's some wiggle room with your departure dates and times, you could bag a cheap last-minute fare.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Port-au-Prince (PAP-Toussaint Louverture Intl.)?
If you reserved your ORD to PAP flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

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*Available to One Key members.