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Freeport

$256+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheap 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 December 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/288:09 pmORD - FPO
1 stop15h 16mMultiple Airlines
Sun 1/411:00 amFPO - ORD
2 stops32h 33mMultiple Airlines
Deal found 12/21$856
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/2512:39 pmORD - FPO
2 stops23h 51mMultiple Airlines
Mon 12/2910:45 amFPO - ORD
1 stop14h 45mMultiple Airlines
Deal found 12/22$871
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/288:09 pmORD - FPO
1 stop15h 16mMultiple Airlines
Fri 1/210:45 amFPO - ORD
2 stops32h 48mMultiple Airlines
Deal found 12/21$892
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/295:00 amORD - FPO
1 stop5h 50mMultiple Airlines
Sun 1/411:00 amFPO - ORD
2 stops32h 33mMultiple Airlines
Deal found 12/21$911
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/297:00 amORD - FPO
1 stop6h 25mAmerican Airlines
Sun 1/412:50 pmFPO - ORD
1 stop12h 53mAmerican Airlines
Deal found 12/21$922
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Thu 12/255:00 amORD - FPO
1 stop7h 24mAmerican Airlines
Mon 12/2912:50 pmFPO - ORD
1 stop7h 54mAmerican Airlines
Deal found 12/22$942
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/2512:39 pmORD - FPO
2 stops23h 51mMultiple Airlines
Fri 1/210:45 amFPO - ORD
1 stop14h 45mMultiple Airlines
Deal found 12/19$943
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Wed 12/245:00 amORD - FPO
1 stop7h 24mAmerican Airlines
Sat 12/273:05 pmFPO - ORD
1 stop10h 38mAmerican Airlines
Deal found 12/20$967
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/245:00 amORD - FPO
1 stop7h 24mAmerican Airlines
Thu 1/13:05 pmFPO - ORD
1 stop10h 38mAmerican Airlines
Deal found 12/21$1,017

Find 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 December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$405
(Kiwi.com)

One-way from

$256
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$993
Provider with most accurate pricing for Chicago (CHI)-Freeport Grand Bahama Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Freeport Grand Bahama Intl flights.
Search Deals
From Chicago (CHI) to Freeport Grand Bahama Intl
Search Deals
One-way flight from Chicago (CHI) to Freeport Grand Bahama Intl
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 22, 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

Wed 2/4

5:15 am-1:30 pm

1 stop7h 15m

Freeport Grand Bahama Intl

Wed 2/11

10:45 am-9:03 pm

1 stop11h 18m

$405

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 1/18

1:13 pm-11:50 am

1 stop21h 37m

Freeport Grand Bahama Intl

Sun 1/25

10:45 am-11:22 am

1 stop25h 37m

$477

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Wed 1/7

3:26 pm-1:30 pm

1 stop21h 04m

Freeport Grand Bahama Intl

Mon 1/12

10:45 am-11:22 am

1 stop25h 37m

$486

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Tue 3/17

9:40 am-1:30 pm

1 stop26h 50m

Freeport Grand Bahama Intl

Sat 3/21

10:45 am-11:41 pm

1 stop13h 56m

$505

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Mon 1/19

9:10 pm-12:06 pm

2 stops13h 56m

Freeport Grand Bahama Intl

Mon 1/26

12:46 pm-10:34 pm

2 stops10h 48m

$540

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Wed 2/18

5:00 am-12:12 pm

1 stop6h 12m

Freeport Grand Bahama Intl

Mon 2/23

1:52 pm-11:53 pm

1 stop11h 01m

$546

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 2/28

7:00 am-1:45 pm

1 stop5h 45m

Freeport Grand Bahama Intl

Thu 3/5

10:45 am-2:05 pm

3 stops28h 20m

$551

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Wed 12/31

12:09 pm-11:50 am

2 stops22h 41m

$256

ChicagoFreeport

MDW - FPO

MDWFPO

Chicago Midway

Wed 12/31

8:15 am-12:25 pm

2 stops27h 10m

$261

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 12/28

4:44 pm-11:50 am

1 stop18h 06m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 16 results
1
2

Compare providers for flights from Chicago to Freeport

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Freeport in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Freeport, City of Freeport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Freeport, City of Freeport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Freeport, City of Freeport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Freeport, City of Freeport flights, Cheapflights users trust eDreams the most. eDreams 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-Freeport, City of Freeport 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 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 $158). Flying from Chicago to Freeport, City of Freeport in April is currently the most expensive (average of $705). 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 December 22, 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
11,052 reviews

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,052 reviews
American Airlines
7.2
Good
11,052 reviews

Overall

7.2

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 $586 on this airline. American Airlines is currently priced 10% 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 $158). Flying from Chicago to Freeport, City of Freeport in April is currently the most expensive (average of $705). 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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$586Average$764FlexibilityNo cancel feeOn-time71%

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