$236+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Sep 2 — Sep 91
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 3, 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 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/78:05 am
ORD
- FPO
1 stop28h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/78:05 am
ORD
- FPO
1 stop28h 40m
Multiple Airlines
Thu 9/1011:00 am
FPO
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$512
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:05 am
ORD
- FPO
1 stop28h 25m
Multiple Airlines
Wed 9/210:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/258:05 am
ORD
- FPO
1 stop28h 25m
Multiple Airlines
Sun 8/3010:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/311:59 pm
ORD
- FPO
2 stops22h 31m
Multiple Airlines
Thu 9/310:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$585
This Trip.com deal was found by Cheapflights users on 8/1. 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 9/76:05 am
MDW
- FPO
2 stops30h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- MDW
2 stops13h 44m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$653
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 3, 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 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/78:05 am
ORD
- FPO
1 stop28h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 8/3. 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 11/106:05 pm
ORD
- FPO
1 stop16h 16m
American Airlines
Fri 11/1312:01 pm
FPO
- ORD
1 stop13h 43m
American Airlines
Deal found 8/3![American Airlines logo]()
$728
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:10 pm
ORD
- FPO
2 stops15h 20m
Multiple Airlines
Wed 9/210:45 am
FPO
- ORD
2 stops22h 08m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$550
This Trip.com deal was found by Cheapflights users on 8/1. 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 9/76:05 am
MDW
- FPO
2 stops30h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- MDW
2 stops13h 44m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$653
This American Airlines deal was found by Cheapflights users on 8/1. 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 10/207:10 pm
ORD
- FPO
1 stop14h 56m
American Airlines
Sat 10/2411:46 am
FPO
- ORD
1 stop13h 52m
American Airlines
Deal found 8/1![American Airlines logo]()
$768
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/218:05 am
ORD
- FPO
2 stops22h 10m
Multiple Airlines
Fri 8/2810:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$667
This American Airlines deal was found by Cheapflights users on 8/3. 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 1/58:55 pm
ORD
- FPO
2 stops14h 01m
American Airlines
Sat 1/93:56 pm
FPO
- ORD
2 stops8h 04m
American Airlines
Deal found 8/3![American Airlines logo]()
$773
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 12/58:55 pm
ORD
- FPO
2 stops13h 50m
American Airlines
Sat 12/1212:45 pm
FPO
- ORD
2 stops8h 21m
American Airlines
Deal found 7/31![American Airlines logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 12/185:00 am
ORD
- FPO
1 stop7h 30m
Multiple Airlines
Wed 12/2310:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 8/3. 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 8/155:59 pm
ORD
- FPO
1 stop16h 03m
American Airlines
Sat 8/221:49 pm
FPO
- ORD
1 stop9h 42m
American Airlines
Deal found 8/3![American Airlines logo]()
$864
Last-minute flights from Chicago to FreeportDiscover last-minute flight deals from Chicago to Freeport. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Freeport. Data last updated August 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/258:05 am
ORD
- FPO
1 stop28h 25m
Multiple Airlines
Sun 8/3010:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:05 am
ORD
- FPO
1 stop28h 25m
Multiple Airlines
Wed 9/210:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/311:59 pm
ORD
- FPO
2 stops22h 31m
Multiple Airlines
Thu 9/310:45 am
FPO
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/78:05 am
ORD
- FPO
1 stop28h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/78:05 am
ORD
- FPO
1 stop28h 40m
Multiple Airlines
Thu 9/1011:00 am
FPO
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$512
This Trip.com deal was found by Cheapflights users on 8/1. 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 9/76:05 am
MDW
- FPO
2 stops30h 40m
Multiple Airlines
Mon 9/1411:00 am
FPO
- MDW
2 stops13h 44m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$653
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 3, 2026.
Search for one-way flight options from Chicago to Freeport. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/207:11 am
ORD
- FPO
1 stop29h 34m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/218:05 am
ORD
- FPO
2 stops33h 10m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 12/298:55 pm
ORD
- FPO
1 stop15h 29m
American Airlines
Deal found 7/30![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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $511 (Kiwi.com) |
One-way from | $236 (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 2,558,603 searches. Data last updated August 3, 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 - FPO
ORDFPO
Chicago O'Hare Intl
Mon 9/7
8:05 am-1:45 pm
1 stop28h 40m
Freeport Grand Bahama Intl
Mon 9/14
11:00 am-12:45 am
2 stops14h 45m
$513
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Thu 8/27
9:10 pm-1:30 pm
2 stops15h 20m
Freeport Grand Bahama Intl
Wed 9/2
10:45 am-7:53 am
2 stops22h 08m
$550
ChicagoFreeport
MDW - FPO
MDWFPO
Chicago Midway
Mon 9/7
6:05 am-1:45 pm
2 stops30h 40m
Freeport Grand Bahama Intl
Mon 9/14
11:00 am-11:44 pm
2 stops13h 44m
$653
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Fri 8/21
8:05 am-7:15 am
2 stops22h 10m
Freeport Grand Bahama Intl
Fri 8/28
10:45 am-12:50 pm
1 stop27h 05m
$667
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Fri 12/18
5:00 am-1:30 pm
1 stop7h 30m
Freeport Grand Bahama Intl
Wed 12/23
10:45 am-12:50 pm
1 stop27h 05m
$713
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Tue 11/10
6:05 pm-11:21 am
1 stop16h 16m
Freeport Grand Bahama Intl
Fri 11/13
12:01 pm-12:44 am
1 stop13h 43m
$728
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Tue 10/20
7:10 pm-11:06 am
1 stop14h 56m
Freeport Grand Bahama Intl
Sat 10/24
11:46 am-12:38 am
1 stop13h 52m
$768
Quickest round-trip
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Tue 1/5
8:55 pm-11:56 am
2 stops14h 01m
Freeport Grand Bahama Intl
Sat 1/9
3:56 pm-11:00 pm
2 stops8h 04m
$773
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Sat 12/5
8:55 pm-11:45 am
2 stops13h 50m
Freeport Grand Bahama Intl
Sat 12/12
12:45 pm-8:06 pm
2 stops8h 21m
$773
ChicagoFreeport
ORD - FPO
ORDFPO
Chicago O'Hare Intl
Sat 8/15
5:59 pm-11:02 am
1 stop16h 03m
Freeport Grand Bahama Intl
Sat 8/22
1:49 pm-10:31 pm
1 stop9h 42m
$864
Showing 1-10 of 13 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 3, 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
Food
6.4
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.8
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.5
Food
6.4
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.8
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 3, 2026.
Chicago and Freeport flights
Browse other Chicago and Freeport flight options. Last updated on August 3, 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 3, 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$587 | Average$768 | FlexibilityNo cancel fee | On-time71% |