$369+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Sep 30 — Oct 71
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 31, 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 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 11/148:00 am -
1 stop28h 30m
Sat 11/2110:45 am -
1 stop14h 31m
Deal found 8/27![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/198:04 am -
1 stop28h 26m
Thu 10/227:30 pm -
2 stops21h 00m
Deal found 8/27![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 11/268:36 am -
1 stop27h 54m
Wed 12/210:45 am -
1 stop27h 05m
Deal found 8/27![Multiple Airlines logo]()
$601
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/272:46 pm -
2 stops45h 44m
Sun 10/410:45 am -
1 stop29h 00m
Deal found 8/28![Multiple Airlines logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/127:11 am -
1 stop27h 39m
Thu 9/1710:45 am -
1 stop29h 00m
Deal found 8/29![Multiple Airlines logo]()
$611
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/66:45 pm -
2 stops45h 45m
Deal found 8/30![Multiple Airlines logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 11/258:36 am -
1 stop27h 54m
Wed 12/210:45 am -
1 stop27h 05m
Deal found 8/27![Multiple Airlines logo]()
$623
This Trip.com deal was found by Cheapflights users on 8/27. 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 9/216:25 am -
3 stops23h 50m
Sun 9/2710:45 am -
2 stops13h 59m
Deal found 8/27![Multiple Airlines logo]()
$1,198
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 31, 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 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/272:46 pm -
2 stops45h 44m
Sun 10/410:45 am -
1 stop29h 00m
Deal found 8/28![Multiple Airlines logo]()
$604
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sun 1/178:55 pm -
2 stops14h 01m
Sun 1/313:56 pm -
2 stops9h 06m
Deal found 8/27![American Airlines logo]()
$728
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/108:04 am -
1 stop28h 26m
Sat 10/177:30 pm -
2 stops37h 01m
Deal found 8/28![Multiple Airlines logo]()
$676
This American Airlines deal was found by Cheapflights users on 8/30. 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 1/256:00 am -
2 stops9h 31m
Fri 1/295:11 pm -
1 stop8h 39m
Deal found 8/30![American Airlines logo]()
$733
This American Airlines deal was found by Cheapflights users on 8/30. 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.
Fri 10/237:29 pm -
1 stop14h 38m
Fri 10/3011:47 am -
1 stop7h 27m
Deal found 8/30![American Airlines logo]()
$768
This American Airlines deal was found by Cheapflights users on 8/31. 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 12/96:59 am -
1 stop6h 43m
Mon 12/143:22 pm -
1 stop7h 14m
Deal found 8/31![American Airlines logo]()
$773
This American Airlines deal was found by Cheapflights users on 8/29. 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.
Sat 12/129:11 pm -
2 stops13h 10m
Sat 12/193:41 pm -
2 stops9h 18m
Deal found 8/29![American Airlines logo]()
$773
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 12/59:11 pm -
2 stops13h 10m
Mon 12/73:22 pm -
2 stops9h 39m
Deal found 8/28![American Airlines logo]()
$773
This American Airlines deal was found by Cheapflights users on 8/30. 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 10/219:00 pm -
2 stops13h 07m
Wed 10/2811:47 am -
2 stops9h 15m
Deal found 8/30![American Airlines logo]()
$778
This Trip.com deal was found by Cheapflights users on 8/27. 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 9/216:25 am -
3 stops23h 50m
Sun 9/2710:45 am -
2 stops13h 59m
Deal found 8/27![Multiple Airlines logo]()
$1,198
This American Airlines deal was found by Cheapflights users on 8/29. 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 8/29![American Airlines logo]()
$816
Last-minute flights from Chicago to FreeportDiscover last-minute flight deals from Chicago to Freeport. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Freeport. Data last updated August 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/67:06 am -
2 stops29h 39m
Sat 9/129:30 am -
1 stop6h 50m
Deal found 8/29![Multiple Airlines logo]()
$665
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/127:11 am -
1 stop27h 39m
Thu 9/1710:45 am -
1 stop29h 00m
Deal found 8/29![Multiple Airlines logo]()
$611
This Trip.com deal was found by Cheapflights users on 8/27. 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 9/217:11 am -
2 stops25h 49m
Sun 9/2710:45 am -
2 stops15h 00m
Deal found 8/27![Multiple Airlines logo]()
$700
This Trip.com deal was found by Cheapflights users on 8/27. 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 9/216:25 am -
3 stops23h 50m
Sun 9/2710:45 am -
2 stops13h 59m
Deal found 8/27![Multiple Airlines logo]()
$1,198
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 9/257:11 am -
1 stop27h 39m
Mon 9/289:30 am -
1 stop6h 15m
Deal found 8/30![Multiple Airlines logo]()
$651
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/272:46 pm -
2 stops45h 44m
Sun 10/410:45 am -
1 stop29h 00m
Deal found 8/28![Multiple Airlines logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/66:45 pm -
2 stops45h 45m
Deal found 8/30![Multiple Airlines logo]()
$618
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 31, 2026.
Search for one-way flight options from Chicago to Freeport. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/158:26 am -
2 stops9h 34m
Deal found 8/27![Multiple Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 8/28. 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 10/125:05 am -
1 stop5h 02m
Deal found 8/28![American Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 8/27. 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 10/155:05 am -
1 stop5h 02m
Deal found 8/27![American Airlines logo]()
$459
This American Airlines deal was found by Cheapflights users on 8/27. 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 12/299:33 pm -
1 stop12h 47m
Deal found 8/27![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 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $468 (Kiwi.com) |
One-way from | $369 (Kiwi.com) |
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 7,457,451 searches. Data last updated August 31, 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
Sun 9/27
2:46 pm-1:30 pm
2 stops45h 44m
Freeport Grand Bahama Intl
Sun 10/4
10:45 am-2:45 pm
1 stop29h 00m
$604
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 10/10
8:04 am-1:30 pm
1 stop28h 26m
Freeport Grand Bahama Intl
Sat 10/17
7:30 pm-7:31 am
2 stops37h 01m
$676
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sun 1/17
8:55 pm-11:56 am
2 stops14h 01m
Freeport Grand Bahama Intl
Sun 1/31
3:56 pm-12:02 am
2 stops9h 06m
$728
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Mon 1/25
6:00 am-4:31 pm
2 stops9h 31m
Freeport Grand Bahama Intl
Fri 1/29
5:11 pm-12:50 am
1 stop8h 39m
$733
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Fri 10/23
7:29 pm-11:07 am
1 stop14h 38m
Freeport Grand Bahama Intl
Fri 10/30
11:47 am-6:14 pm
1 stop7h 27m
$768
Quickest round-trip
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Wed 12/9
6:59 am-2:42 pm
1 stop6h 43m
Freeport Grand Bahama Intl
Mon 12/14
3:22 pm-9:36 pm
1 stop7h 14m
$773
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 12/12
9:11 pm-11:21 am
2 stops13h 10m
Freeport Grand Bahama Intl
Sat 12/19
3:41 pm-11:59 pm
2 stops9h 18m
$773
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 12/5
9:11 pm-11:21 am
2 stops13h 10m
Freeport Grand Bahama Intl
Mon 12/7
3:22 pm-12:01 am
2 stops9h 39m
$773
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Wed 10/21
9:00 pm-11:07 am
2 stops13h 07m
Freeport Grand Bahama Intl
Wed 10/28
11:47 am-8:02 pm
2 stops9h 15m
$778
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
$816
Showing 1-10 of 14 resultsSorted 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 31, 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.
Boarding
7.5
Overall
7.1
Entertainment
6.8
Food
6.4
Crew
7.9
Comfort
7.2
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.5
Overall
7.1
Entertainment
6.8
Food
6.4
Crew
7.9
Comfort
7.2
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
Complete your trip to Freeport by adding a car rental and/or hotel reservation to your travel itinerary.
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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 31, 2026.
Chicago and Freeport flights
Browse other Chicago and Freeport flight options. Last updated on August 31, 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 31, 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 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$587 | Average$762 | FlexibilityNo cancel fee | On-time71% |