C$279 Cheap Flights from Chicago (CHIA) to Freeport (FPO)

Compare Chicago to Freeport flight deals

Find the cheapest month or even day of the year to fly to Freeport

Earn frequent flyer miles on flights booked through Skyscanner

Flight deals from Chicago to Freeport

Looking for a cheap last-minute deal or the best return flight from Chicago to Freeport Airport? If you want to travel next month, return fares start from C$589. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Freeport

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Freeport flights are currently cheapest in May.

Chicago to Freeport: Alternative routes

Compare routes from Chicago to Freeport below. You may find an airport to fly into that's cheaper, faster, or easier than Freeport.

Chicago to Freeport: Flight information

The things to know before you go.
Cheapest flight foundC$279
Cheapest month to flyMay

Finding cheap flights from Chicago to Freeport: Frequently asked questions

The best price we found for a return flight from Chicago to Freeport is C$584. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Freeport. But we found flights with one stop from C$584.
As of April 2026, there are no flights flying from Chicago to Freeport.
The cheapest month to fly from Chicago to Freeport is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Freeport Airport on Tuesday, May 26, 2026.
No airlines currently offer direct flights between Chicago and Freeport Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Freeport but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Freeport is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Freeport is Frontier Airlines .

Flying from Chicago to Grand Bahama International Airport (FPO): what you need to know

  • Chicago has two main airports that could be the jumping-off point for your adventure. Explore your options for booking a flight from Chicago to Grand Bahama International Airport (FPO) flying out of O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • The timezone in Freeport is UTC-4, which is 1 hour ahead of Chicago. Grand Bahama International Airport is located in Freeport.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Be at the airport on time to board your flight from Chicago to FPO.

  • August is a busy time to fly out. If you're heading away then or during a major holiday like Christmas, be there even earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international journeys.

Airports in Chicago

O'Hare International Airport (ORD)

  • Stopovers are the ideal opportunity to take a travel break — and perhaps even visit a new city. When searching for flights from Chicago to FPO leaving from O'Hare International Airport (ORD), deselect the 'Direct flights only' box to see where you can stop along the way. Popular options include:

    • Miami International Airport (MIA)

    • Fort Lauderdale-Hollywood International Airport (FLL)

    • Charlotte Douglas International Airport (CLT)

  • ORD is around 40 kilometres from the centre of Chicago. To help you work out how to get there, use Google Maps. This useful traveller tool will give you the best route and available public transport options.

  • Booked an early flight from Chicago to Grand Bahama International Airport? Avoid the last-minute rush to the terminal (and get some extra shut-eye) by picking one of these hotels close to O'Hare International Airport:

Chicago Midway International Airport (MDW)

  • Break up your flight from Chicago to Grand Bahama International Airport with a stop so you can stretch your legs or perhaps go somewhere you've never been before. Popular stopovers between Chicago Midway International Airport and FPO are:

    • Fort Lauderdale-Hollywood International Airport (FLL)

    • Charlotte Douglas International Airport (CLT)

    • Miami International Airport (MIA)

  • With public transport, you can travel from central Chicago to MDW in around 46 minutes. The terminal is roughly 19 kilometres away, and making the journey by car takes approximately 21 minutes.

  • Want to spoil yourself with an extra night away before your flight from Chicago to FPO? Check in to a hotel near Chicago Midway International Airport before your break officially starts. These stays are calling your name:

About Grand Bahama International Airport (FPO)

Getting from Grand Bahama International Airport (FPO) to central Freeport

  • From Grand Bahama International Airport, Freeport is approximately 8 kilometres away. It takes around 9 minutes to reach the centre driving.

How to find the cheapest flights from Chicago to Grand Bahama International Airport (FPO)

  • C$279 is the cheapest price we've found for a one-way ticket from Chicago to Grand Bahama International Airport. Return flights start from C$584. Fares are subject to availability and may change at any time.

  • It's often best to book as early as possible if you want to find flight tickets from Chicago to FPO. That's because airlines change prices based on demand, which tends to increase closer to the date of departure.

  • The 'Whole month' tool shows you the cheapest tickets from Chicago to Grand Bahama International Airport across every month. It's an easy way to snap up a bargain if your dates are flexible.

  • Set up a Price Alert and keep an eye on changes on this route through push notifications or email. We'll let you know when prices drop. Good timing makes all the difference when searching for flight tickets from Chicago to FPO.

  • Use the filters to tailor your flights from Chicago to Grand Bahama International Airport. Simply select your ideal arrival and departure times, number of stops and airlines. You can also sort your results by 'Cheapest' to see the best deals.

The best time to fly from Chicago to Grand Bahama International Airport (FPO)

  • August is the most popular month to board a flight from Chicago to Grand Bahama International Airport while February is the quietest. To work out the best time to go to Freeport, consider whether you prefer a lively vibe or a quieter pace.

  • Schedule your flight from Chicago to FPO for August if you're eager to explore the city during its warmest month. Expect temperatures in Freeport to range from 26ºC to 30ºC.

  • January has average temperatures of between 18ºC and 23ºC. Search for cheap flights from Chicago to Grand Bahama International Airport sometime then if you want to travel when it's cooler.

More about Freeport

  • After booking your flight from Chicago to Grand Bahama International Airport, think about where to rest your head in this city. Make one of these options your base for exploring Freeport:

  • One of the best ways to get a feel for Freeport is to check out its leading attractions. Some highlights include Bahamian Brewery, Garden of the Groves and Xanadu Beach.

Complete your Freeport trip with a car rental

  • We use the same magic that helped you find your cheap flight from Chicago to Grand Bahama International Airport to track down your ideal ride. Browse our car rentals in Freeport and easily compare your options. Plus you'll find all the info you need to know, from the most popular rental company to the best time to book.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.