HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Port Au Prince

$2,694+ Cheap flights from Midway (MDW) to Port Au Prince (PAP)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PAP
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Port Au Prince with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Port Au Prince

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Port Au Prince (PAP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 6, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$2,694
(Trip.com)
Provider with most accurate pricing for Chicago Midway-Port Au Prince Mais Gate flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Port Au Prince Mais Gate flights.
Search Deals
From Chicago Midway to Port Au Prince Mais Gate
Search Deals

Find flight deals from Midway to Port Au Prince

Cheapest flights from Midway to Port Au Prince
Explore the most affordable flight options available from Midway to Port Au Prince. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2025.

This Trip.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:05 amMDW - PAP
3 stops48h 10mMultiple Airlines
Thu 11/272:00 pmPAP - MDW
3 stops33h 43mMultiple Airlines
Deal found 10/6$2,694

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Port Au Prince that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 6, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Port Au Prince that are best for you.

Fly from

Midway

Fly to

Port Au Prince

Route

Depart

Return

Price

ChicagoPort Au Prince

MDW - PAP

MDWPAP

Chicago Midway

Thu 11/20

6:05 am-7:15 am

3 stops48h 10m

Port Au Prince Mais Gate

Thu 11/27

2:00 pm-10:43 pm

3 stops33h 43m

$2,694

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Port Au Prince flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago Midway Airport-Port Au Prince flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Port Au Prince flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Port Au Prince flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Port Au Prince flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Port Au Prince

Have a flexible travel schedule? Discover the best time to fly to Port Au Prince from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Port Au Prince. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Port Au Prince from Chicago Midway?

    Most people fly into Port Au Prince Mais Gate (PAP) if they book a flight to Port Au Prince from Chicago Midway. On average, Mais Gate has 0 inbound flights from Chicago Midway per day from 0 airlines. Port Au Prince Mais Gate is conveniently located just 2.4 mi from Port Au Prince’s city center.

  • Can I find deals for flights from Midway to Port Au Prince that include hotel bookings?

    Yes. In addition to deals on Midway to Port Au Prince flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Port Au Prince?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Port Au Prince.

  • Can I find deals for business class flights from Midway to Port Au Prince?

    Yes. Cheapflights offers flight deals from Midway to Port Au Prince by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Port Au Prince?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Port Au Prince (average of $247). Flying from Chicago Midway Airport to Port Au Prince in December is currently the most expensive (average of $451). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Port Au Prince

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Port Au Prince flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.