Freeport

$209+ Cheap flights from Chicago (CHI) to Freeport (FPO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Jul 8 — Jul 151
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Cheap flight deals from Chicago to Freeport

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Freeport (FPO). 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 July 3, 2025.

Round-trip from

$477
(Kiwi.com)

One-way from

$209
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$691
From Chicago (CHI) to Freeport Grand Bahama Intl
One-way flight from Chicago (CHI) to Freeport Grand Bahama Intl
Highest demand for flights based on searches. 14% potential increase in price ($105 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Average for round-trip flights in July 2025

Find flight deals from Chicago to Freeport

Cheapest flights from Chicago to Freeport
Explore the most affordable flight options available from Chicago to Freeport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:12 pmORD - FPO
1 stop19h 38mMultiple Airlines
Wed 8/2711:00 amFPO - ORD
1 stop13h 59mMultiple Airlines
Deal found 7/2$477
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:12 amORD - FPO
2 stops9h 13mAmerican Airlines
Fri 12/126:35 pmFPO - ORD
1 stop15h 28mAmerican Airlines
Deal found 7/3$591

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Freeport 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 July 3, 2025.
Use the filters below to find and compare flights from Chicago to Freeport that are best for you.

Fly from

Chicago

Fly to

Freeport

Route

Depart

Return

Price

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Thu 8/21

8:12 pm-4:50 pm

1 stop19h 38m

Freeport Grand Bahama Intl

Wed 8/27

11:00 am-11:59 pm

1 stop13h 59m

$477

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Fri 8/29

5:05 pm-9:41 am

1 stop15h 36m

Freeport Grand Bahama Intl

Sun 8/31

2:28 pm-9:25 pm

1 stop7h 57m

$592

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Wed 8/20

5:05 am-1:45 pm

1 stop7h 40m

$209

ChicagoFreeport

MDW - FPO

MDWFPO

Chicago Midway

Wed 8/20

8:00 am-12:25 pm

2 stops27h 25m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Best time to book a flight from Chicago to Freeport

Have a flexible travel schedule? Discover the best time to fly to Freeport from Chicago 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Freeport

What is the cheapest month to book a flight from Chicago to Freeport, City of Freeport?

Currently, September is the cheapest month in which you can book a flight from Chicago to Freeport, City of Freeport (average of $298). Flying from Chicago to Freeport, City of Freeport in December is currently the most expensive (average of $591). 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.

How much does it cost to fly round-trip from Chicago to Freeport, City of Freeport?

Reviews of airlines servicing Freeport

Get insights into the airlines that provide service to Freeport. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Freeport. Reviews last updated July 3, 2025.
Get a feel of what it's like to fly with American Airlines from Chicago to Freeport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.2

Food

6.5

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

Overall

7.2

Food

6.5

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Freeport. 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 Freeport from Chicago?

    Located just 4.1 mi from the city center, Freeport Grand Bahama Intl is the airport most travelers will use when flying to Freeport from Chicago. Booking flights from Chicago to Grand Bahama Intl (FPO) should be relatively easy as there are 0 daily inbound flights from Chicago from 1 airline.

  • What is the cheapest airline to fly from Chicago to Freeport, City of Freeport round-trip?

    Our cheapest airline available from Chicago to Freeport, City of Freeport is American Airlines. Our recent data shows that you can find tickets from as low as $592 on this airline. American Airlines is currently priced 8% below the average price you’ll pay for this route.

  • Can I find deals for flights from Chicago to Freeport that include hotel bookings?

    Yes. In addition to deals on Chicago to Freeport flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Freeport?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Freeport.

  • Can I find deals for business class flights from Chicago to Freeport?

    Yes. Cheapflights offers flight deals from Chicago to Freeport 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 to Freeport, City of Freeport?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Freeport, City of Freeport (average of $298). Flying from Chicago to Freeport, City of Freeport in December is currently the most expensive (average of $591). 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

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Top airline flying from Chicago to Freeport

Discover the top airline that operate flights from Chicago to Freeport. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$555Average$701FlexibilityNo cancel feeOn-time71%

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