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Freeport

$586+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Find cheap flights from Chicago to Freeport with Cheapflights

1. Tell us where you want to go

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2. Select your favorite providers

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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 May 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/118:05 am
ORD
-
FPO
1 stop28h 40m
Multiple Airlines
Sat 7/1811:00 am
FPO
-
ORD
2 stops21h 53m
Multiple Airlines
Deal found 5/7$586
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/21:29 pm
ORD
-
FPO
2 stops23h 01m
Multiple Airlines
Sun 6/711:00 am
FPO
-
ORD
1 stop26h 24m
Multiple Airlines
Deal found 5/9$605
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/16:55 am
ORD
-
FPO
2 stops29h 35m
Multiple Airlines
Sun 6/711:00 am
FPO
-
ORD
1 stop26h 24m
Multiple Airlines
Deal found 5/9$609
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/14:59 pm
ORD
-
FPO
1 stop18h 26m
Multiple Airlines
Mon 7/66:45 pm
FPO
-
ORD
2 stops42h 40m
Multiple Airlines
Deal found 5/6$614
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/21:29 pm
ORD
-
FPO
2 stops23h 01m
Multiple Airlines
Tue 6/910:45 am
FPO
-
ORD
1 stop26h 39m
Multiple Airlines
Deal found 5/9$626
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/16:55 am
ORD
-
FPO
2 stops29h 35m
Multiple Airlines
Tue 6/910:45 am
FPO
-
ORD
1 stop26h 39m
Multiple Airlines
Deal found 5/9$630
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/197:52 am
ORD
-
FPO
1 stop28h 38m
Multiple Airlines
Mon 6/221:40 pm
FPO
-
ORD
2 stops31h 10m
Multiple Airlines
Deal found 5/5$633
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 8/171:50 pm
ORD
-
FPO
2 stops22h 40m
Multiple Airlines
Thu 8/201:40 pm
FPO
-
ORD
1 stop10h 34m
Multiple Airlines
Deal found 5/8$642
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/41:29 pm
ORD
-
FPO
2 stops23h 01m
Multiple Airlines
Tue 6/910:45 am
FPO
-
ORD
1 stop26h 39m
Multiple Airlines
Deal found 5/9$644
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/31:29 pm
ORD
-
FPO
2 stops21h 21m
Multiple Airlines
Tue 6/910:45 am
FPO
-
ORD
1 stop26h 39m
Multiple Airlines
Deal found 5/9$650
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 6/27:29 am
ORD
-
FPO
1 stop27h 21m
Multiple Airlines
Mon 6/810:45 am
FPO
-
ORD
2 stops22h 18m
Multiple Airlines
Deal found 5/9$657

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$586
(Kiwi.com)
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

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 May 10, 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 7/1

4:59 pm-12:25 pm

1 stop18h 26m

Freeport Grand Bahama Intl

Mon 7/6

6:45 pm-12:25 pm

2 stops42h 40m

$614

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Mon 8/17

1:50 pm-1:30 pm

2 stops22h 40m

Freeport Grand Bahama Intl

Thu 8/20

1:40 pm-11:14 pm

1 stop10h 34m

$642

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Thu 6/4

1:29 pm-1:30 pm

2 stops23h 01m

Freeport Grand Bahama Intl

Tue 6/9

10:45 am-12:24 pm

1 stop26h 39m

$644

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Mon 6/1

8:20 am-1:30 pm

1 stop28h 10m

Freeport Grand Bahama Intl

Mon 6/8

10:45 am-8:03 am

2 stops22h 18m

$667

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 8/15

7:00 pm-11:02 am

1 stop15h 02m

Freeport Grand Bahama Intl

Sat 8/22

11:42 am-11:00 pm

1 stop12h 18m

$678
Quickest round-trip

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Tue 7/7

6:59 am-1:13 pm

1 stop5h 14m

Freeport Grand Bahama Intl

Wed 7/15

1:53 pm-11:30 pm

2 stops10h 37m

$683

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sat 10/24

8:35 pm-12:55 pm

2 stops15h 20m

Freeport Grand Bahama Intl

Thu 10/29

3:10 pm-9:22 pm

1 stop7h 12m

$683

ChicagoFreeport

ORD - FPO

ORDFPO

Chicago O'Hare Intl

Sun 8/23

6:10 am-1:09 pm

1 stop5h 59m

Freeport Grand Bahama Intl

Sun 8/30

11:42 am-11:00 pm

1 stop12h 18m

$683

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

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 May.
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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Freeport, City of Freeport (average of $122). Flying from Chicago to Freeport, City of Freeport in April is currently the most expensive (average of $661). 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 May 10, 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
11,667 reviews

Boarding

7.5

Food

6.4

Overall

7.1

Crew

7.9

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Boarding

7.5

Food

6.4

Overall

7.1

Crew

7.9

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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.

  • How long is the flight from Chicago to Freeport, City of Freeport?

    For as low as $678, American Airlines can have you in Freeport, City of Freeport from Chicago in 15h 02m. There are 1186 mi between Chicago and Freeport, City of Freeport.

  • 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.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Freeport, City of Freeport (average of $122). Flying from Chicago to Freeport, City of Freeport in April is currently the most expensive (average of $661). 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$587Average$822FlexibilityNo cancel feeOn-time71%

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