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Freeport

$454+ Cheap flights from Chicago (CHI) to Freeport (FPO)

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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$454
(Mytrip)

Popular in

December

Cheapest in

October
From Chicago (CHI) to Freeport Grand Bahama Intl
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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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 September 16, 2025.

This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/95:05 amORD - FPO
1 stop7h 50mMultiple Airlines
Sun 11/1611:00 amFPO - ORD
1 stop13h 42mMultiple Airlines
Deal found 9/14$454
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 12/58:41 amORD - FPO
1 stop6h 54mMultiple Airlines
Sun 12/75:30 pmFPO - ORD
1 stop7h 12mMultiple Airlines
Deal found 9/14$457
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 11/85:59 pmORD - FPO
1 stop18h 56mMultiple Airlines
Tue 11/1110:00 amFPO - ORD
1 stop9h 23mMultiple Airlines
Deal found 9/14$465
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:05 amORD - FPO
1 stop7h 25mMultiple Airlines
Mon 10/610:45 amFPO - ORD
1 stop8h 53mMultiple Airlines
Deal found 9/16$468
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/75:05 amORD - FPO
1 stop7h 25mMultiple Airlines
Tue 10/1410:45 amFPO - ORD
1 stop14h 00mMultiple Airlines
Deal found 9/15$473
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 12/210:49 amORD - FPO
1 stop25h 41mMultiple Airlines
Mon 12/810:45 amFPO - ORD
1 stop13h 57mMultiple Airlines
Deal found 9/15$499

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 September 16, 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

Sun 11/9

5:05 am-1:55 pm

1 stop7h 50m

Freeport Grand Bahama Intl

Sun 11/16

11:00 am-11:42 pm

1 stop13h 42m

$454

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 11/8

5:59 pm-1:55 pm

1 stop18h 56m

Freeport Grand Bahama Intl

Tue 11/11

10:00 am-6:23 pm

1 stop9h 23m

$465

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Mon 9/29

5:05 am-1:30 pm

1 stop7h 25m

Freeport Grand Bahama Intl

Mon 10/6

10:45 am-6:38 pm

1 stop8h 53m

$468

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Tue 10/7

5:05 am-1:30 pm

1 stop7h 25m

Freeport Grand Bahama Intl

Tue 10/14

10:45 am-11:45 pm

1 stop14h 00m

$473

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Tue 12/2

10:49 am-1:30 pm

1 stop25h 41m

Freeport Grand Bahama Intl

Mon 12/8

10:45 am-11:42 pm

1 stop13h 57m

$499

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 11/8

8:30 pm-1:55 pm

2 stops16h 25m

Freeport Grand Bahama Intl

Sat 11/15

11:00 am-9:00 pm

1 stop11h 00m

$507

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Fri 12/5

8:30 pm-1:30 pm

2 stops16h 00m

Freeport Grand Bahama Intl

Sun 12/7

5:30 pm-11:42 pm

1 stop7h 12m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 $299). 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.

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 September 16, 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.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $565 on this airline. American Airlines is currently priced 12% 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 $299). 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

Browse thousands of different options on Cheapflights for your next trip

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$565Average$763FlexibilityNo cancel feeOn-time71%

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