$481+ 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Freeport with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Freeport
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to FreeportExplore 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 August 19, 2026.
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 August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/157:11 am -
1 stop27h 39m
Mon 9/2811:00 am -
2 stops25h 51m
Deal found 8/16![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Thu 10/157:45 am -
1 stop29h 00m
Wed 10/2111:00 am -
2 stops22h 15m
Deal found 8/15![Multiple Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Mon 9/287:11 am -
1 stop27h 39m
Mon 10/511:00 am -
2 stops25h 51m
Deal found 8/14![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/197:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/297:11 am -
1 stop27h 39m
Tue 10/610:45 am -
2 stops26h 06m
Deal found 8/15![Multiple Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/187:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Thu 9/177:11 am -
1 stop27h 39m
Sun 9/209:30 am -
1 stop6h 15m
Deal found 8/17![Multiple Airlines logo]()
$603
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
2 stops30h 20m
Sun 9/2011:00 am -
2 stops13h 44m
Deal found 8/17![Multiple Airlines logo]()
$610
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
3 stops23h 50m
Mon 10/511:00 am -
2 stops13h 44m
Deal found 8/14![Multiple Airlines logo]()
$639
Best flights from Chicago to FreeportDiscover carefully curated flight deals from Chicago to Freeport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
Discover carefully curated flight deals from Chicago to Freeport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Mon 9/287:11 am -
1 stop27h 39m
Mon 10/511:00 am -
2 stops25h 51m
Deal found 8/14![Multiple Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/215:05 am -
1 stop5h 02m
Wed 10/2811:47 am -
1 stop7h 27m
Deal found 8/18![American Airlines logo]()
$733
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/197:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/297:11 am -
1 stop27h 39m
Tue 10/610:45 am -
2 stops26h 06m
Deal found 8/15![Multiple Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/187:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$540
This American Airlines deal was found by Cheapflights users on 8/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:29 pm -
1 stop14h 38m
Wed 10/2111:47 am -
1 stop12h 46m
Deal found 8/15![American Airlines logo]()
$768
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
2 stops30h 20m
Sun 9/2011:00 am -
2 stops13h 44m
Deal found 8/17![Multiple Airlines logo]()
$610
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
3 stops23h 50m
Mon 10/511:00 am -
2 stops13h 44m
Deal found 8/14![Multiple Airlines logo]()
$639
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:25 am -
2 stops29h 20m
Sun 9/2011:00 am -
2 stops14h 45m
Deal found 8/17![Multiple Airlines logo]()
$685
Last-minute flights from Chicago to FreeportDiscover last-minute flight deals from Chicago to Freeport. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Freeport. Data last updated August 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/157:11 am -
1 stop27h 39m
Mon 9/2811:00 am -
2 stops25h 51m
Deal found 8/16![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Thu 9/177:11 am -
1 stop27h 39m
Sun 9/209:30 am -
1 stop6h 15m
Deal found 8/17![Multiple Airlines logo]()
$603
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
2 stops30h 20m
Sun 9/2011:00 am -
2 stops13h 44m
Deal found 8/17![Multiple Airlines logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/187:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/197:11 am -
1 stop27h 39m
Tue 9/229:30 am -
1 stop6h 50m
Deal found 8/18![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Mon 9/287:11 am -
1 stop27h 39m
Mon 10/511:00 am -
2 stops25h 51m
Deal found 8/14![Multiple Airlines logo]()
$504
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 am -
3 stops23h 50m
Mon 10/511:00 am -
2 stops13h 44m
Deal found 8/14![Multiple Airlines logo]()
$639
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/297:11 am -
1 stop27h 39m
Tue 10/610:45 am -
2 stops26h 06m
Deal found 8/15![Multiple Airlines logo]()
$533
One-way flights from Chicago to FreeportSearch for one-way flight options from Chicago to Freeport. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
Search for one-way flight options from Chicago to Freeport. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:47 pm -
1 stop15h 33m
Deal found 8/14![American Airlines logo]()
$481
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $496 (Kiwi.com) |
One-way from | $481 (American Airlines) |
Popular in | August |
Cheapest in | December |
Average price | $869 |
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 August 19, 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
Cheapest round-trip
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Mon 9/28
7:11 am-11:50 am
1 stop27h 39m
Freeport Grand Bahama Intl
Mon 10/5
11:00 am-11:51 am
2 stops25h 51m
$504
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 9/19
7:11 am-11:50 am
1 stop27h 39m
Freeport Grand Bahama Intl
Tue 9/22
9:30 am-3:20 pm
1 stop6h 50m
$522
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Tue 9/29
7:11 am-11:50 am
1 stop27h 39m
Freeport Grand Bahama Intl
Tue 10/6
10:45 am-11:51 am
2 stops26h 06m
$533
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Fri 9/18
7:11 am-11:50 am
1 stop27h 39m
Freeport Grand Bahama Intl
Tue 9/22
9:30 am-3:20 pm
1 stop6h 50m
$540
ChicagoFreeport
MDW Chicago Midway - FPO Freeport Grand Bahama Intl
MDWFPO
Chicago Midway
Thu 9/17
6:25 am-1:45 pm
2 stops30h 20m
Freeport Grand Bahama Intl
Sun 9/20
11:00 am-11:44 pm
2 stops13h 44m
$610
ChicagoFreeport
MDW Chicago Midway - FPO Freeport Grand Bahama Intl
MDWFPO
Chicago Midway
Mon 9/28
6:25 am-7:15 am
3 stops23h 50m
Freeport Grand Bahama Intl
Mon 10/5
11:00 am-11:44 pm
2 stops13h 44m
$639
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Thu 9/17
7:25 am-1:45 pm
2 stops29h 20m
Freeport Grand Bahama Intl
Sun 9/20
11:00 am-12:45 am
2 stops14h 45m
$685
Quickest round-trip
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Wed 10/21
5:05 am-11:07 am
1 stop5h 02m
Freeport Grand Bahama Intl
Wed 10/28
11:47 am-6:14 pm
1 stop7h 27m
$733
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Thu 10/15
7:29 pm-11:07 am
1 stop14h 38m
Freeport Grand Bahama Intl
Wed 10/21
11:47 am-11:33 pm
1 stop12h 46m
$768
Cheapest one-way
Quickest one-way
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Tue 12/29
6:47 pm-11:20 am
1 stop15h 33m
$481
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
CHI-FPO
ORD-FPO
MDW-FPO
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
CHI-FPO
ORD-FPO
MDW-FPO
No data available for this route at this time. Please check back soon.
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 August 19, 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.
Crew
7.9
Boarding
7.5
Food
6.4
Entertainment
6.8
Comfort
7.2
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Boarding
7.5
Food
6.4
Entertainment
6.8
Comfort
7.2
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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.
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Complete your trip
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Other flights to Freeport
Explore flights to Freeport departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 19, 2026.
Chicago and Freeport flights
Browse other Chicago and Freeport flight options. Last updated on August 19, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$587 | Average$768 | FlexibilityNo cancel fee | On-time71% |