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Freeport

$528+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
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 July 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
ORD
-
FPO
2 stops22h 10m
Multiple Airlines
Wed 8/2610:45 am
FPO
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 7/20$560
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:44 pm
ORD
-
FPO
1 stop15h 21m
Multiple Airlines
Sun 9/611:00 am
FPO
-
ORD
2 stops21h 53m
Multiple Airlines
Deal found 7/16$597
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/268:05 am
ORD
-
FPO
1 stop28h 25m
Multiple Airlines
Sat 8/2910:45 am
FPO
-
ORD
2 stops10h 23m
Multiple Airlines
Deal found 7/19$607
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/81:50 pm
ORD
-
FPO
2 stops22h 40m
Multiple Airlines
Tue 8/1110:45 am
FPO
-
ORD
1 stop26h 30m
Multiple Airlines
Deal found 7/17$610
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:05 am
ORD
-
FPO
1 stop28h 25m
Multiple Airlines
Sat 8/2210:45 am
FPO
-
ORD
2 stops22h 08m
Multiple Airlines
Deal found 7/16$629
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/168:05 am
ORD
-
FPO
1 stop28h 25m
Multiple Airlines
Sun 8/2310:45 am
FPO
-
ORD
1 stop27h 05m
Multiple Airlines
Deal found 7/17$664
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 12/75:00 am
ORD
-
FPO
1 stop7h 30m
Multiple Airlines
Mon 12/141:40 pm
FPO
-
ORD
1 stop24h 31m
Multiple Airlines
Deal found 7/17$674
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 12/215:00 am
ORD
-
FPO
1 stop7h 30m
Multiple Airlines
Mon 12/281:40 pm
FPO
-
ORD
1 stop24h 31m
Multiple Airlines
Deal found 7/17$683

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 July 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$490
(Kiwi.com)

Popular in

June

Cheapest in

December

Average price

$668
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
Highest demand for flights based on searches. 10% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 20, 2026.
Use the filters below to find and compare flights from Chicago to Freeport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Wed 8/19

8:05 am-7:15 am

2 stops22h 10m

Freeport Grand Bahama Intl

Wed 8/26

10:45 am-12:50 pm

1 stop27h 05m

$560

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 8/8

1:50 pm-1:30 pm

2 stops22h 40m

Freeport Grand Bahama Intl

Tue 8/11

10:45 am-12:15 pm

1 stop26h 30m

$610

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 8/16

8:05 am-1:30 pm

1 stop28h 25m

Freeport Grand Bahama Intl

Sun 8/23

10:45 am-12:50 pm

1 stop27h 05m

$664
Quickest round-trip

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Thu 10/15

5:05 am-11:06 am

1 stop5h 01m

Freeport Grand Bahama Intl

Sun 10/18

11:46 am-12:38 am

1 stop13h 52m

$813

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 8/30

8:58 pm-11:02 am

2 stops13h 04m

Freeport Grand Bahama Intl

Sun 9/6

1:49 pm-11:00 pm

2 stops10h 11m

$827

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 8/1

9:29 pm-11:09 am

2 stops12h 40m

Freeport Grand Bahama Intl

Wed 8/5

11:42 am-7:46 pm

2 stops9h 04m

$829
Cheapest one-way
Quickest one-way

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 8/30

6:00 am-1:09 pm

1 stop6h 09m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Sorted by cheapest first

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Freeport, City of Freeport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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 20, 2026.
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
7.1
Good
11,826 reviews

Food

6.4

Crew

7.9

Entertainment

6.8

Boarding

7.5

Overall

7.1

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,826 reviews
American Airlines
7.1
Good
11,826 reviews

Food

6.4

Crew

7.9

Entertainment

6.8

Boarding

7.5

Overall

7.1

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 $587 on this airline. American Airlines is currently priced 14% 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.

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 July 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$587Average$764FlexibilityNo cancel feeOn-time71%

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