$214+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FPO
Dec 10 — Dec 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 November 10, 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 November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:57 pm -
2 stops40h 53m
Wed 1/610:45 am -
1 stop29h 18m
Deal found 11/6![Multiple Airlines logo]()
$603
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Mon 12/218:59 am -
1 stop25h 51m
Mon 12/2810:45 am -
2 stops38h 28m
Deal found 11/7![Multiple Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Sun 12/275:58 am -
2 stops28h 52m
Wed 12/3010:45 am -
1 stop7h 07m
Deal found 11/7![Multiple Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Tue 1/510:45 am -
2 stops13h 47m
Deal found 11/6![Multiple Airlines logo]()
$737
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Thu 12/3110:45 am -
2 stops13h 21m
Deal found 11/6![Multiple Airlines logo]()
$745
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 11/209:20 pm -
2 stops15h 10m
Wed 11/2510:45 am -
1 stop13h 49m
Deal found 11/8![Multiple Airlines logo]()
$769
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Mon 1/410:45 am -
2 stops15h 08m
Deal found 11/6![Multiple Airlines logo]()
$772
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 November 10, 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 November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 1/117:10 am -
1 stop27h 40m
Mon 1/1810:45 am -
1 stop15h 05m
Deal found 11/9![Multiple Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/245:14 am -
1 stop5h 02m
Tue 3/3011:56 am -
1 stop9h 03m
Deal found 11/5![American Airlines logo]()
$864
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 3/288:25 am -
1 stop28h 05m
Sat 4/310:45 am -
1 stop12h 34m
Deal found 11/5![Multiple Airlines logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 11/209:20 pm -
2 stops15h 10m
Wed 11/2510:45 am -
1 stop13h 49m
Deal found 11/8![Multiple Airlines logo]()
$769
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/118:10 am -
2 stops8h 21m
Mon 1/1812:56 pm -
2 stops9h 54m
Deal found 11/9![American Airlines logo]()
$903
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/88:10 am -
2 stops8h 21m
Sun 1/1012:56 pm -
2 stops10h 31m
Deal found 11/6![American Airlines logo]()
$919
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sat 12/198:59 am -
1 stop25h 51m
Sun 12/2710:45 am -
2 stops26h 15m
Deal found 11/6![Multiple Airlines logo]()
$850
This Mytrip deal was found by Cheapflights users on 11/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/275:59 pm -
2 stops17h 06m
Wed 12/3010:45 am -
2 stops13h 02m
Deal found 11/7![Multiple Airlines logo]()
$861
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/281:10 pm -
2 stops23h 20m
Sun 1/310:45 am -
2 stops26h 15m
Deal found 11/6![Multiple Airlines logo]()
$907
Last-minute flights from Chicago to FreeportDiscover last-minute flight deals from Chicago to Freeport. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Freeport. Data last updated November 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Fri 11/209:20 pm -
2 stops15h 10m
Wed 11/2510:45 am -
1 stop13h 49m
Deal found 11/8![Multiple Airlines logo]()
$769
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Mon 12/218:59 am -
1 stop25h 51m
Mon 12/2810:45 am -
2 stops38h 28m
Deal found 11/7![Multiple Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Sun 12/275:58 am -
2 stops28h 52m
Wed 12/3010:45 am -
1 stop7h 07m
Deal found 11/7![Multiple Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:57 pm -
2 stops40h 53m
Wed 1/610:45 am -
1 stop29h 18m
Deal found 11/6![Multiple Airlines logo]()
$603
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Tue 1/510:45 am -
2 stops13h 47m
Deal found 11/6![Multiple Airlines logo]()
$737
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Thu 12/3110:45 am -
2 stops13h 21m
Deal found 11/6![Multiple Airlines logo]()
$745
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/285:01 am -
1 stop6h 04m
Mon 1/410:45 am -
2 stops15h 08m
Deal found 11/6![Multiple Airlines logo]()
$772
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 November 10, 2026.
Search for one-way flight options from Chicago to Freeport. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/66:07 am -
1 stop28h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sat 12/58:30 am -
2 stops26h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 11/274:00 pm -
1 stop18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sat 11/284:00 pm -
1 stop18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/710:29 pm -
3 stops18h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 11/5. 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 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 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$371
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (Kiwi.com) |
One-way from | $214 (Kiwi.com) |
Popular in | August |
Cheapest in | December |
Average price | $748 |
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 November 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
Cheapest round-trip
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 12/5
8:30 am-7:15 am
3 stops21h 45m
Freeport Grand Bahama Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$289
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Fri 11/27
5:25 am-11:50 am
2 stops29h 25m
Freeport Grand Bahama Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$296
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Tue 12/29
6:47 pm-11:19 am
1 stop15h 32m
Freeport Grand Bahama Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$371
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Mon 1/11
7:10 am-11:50 am
1 stop27h 40m
Freeport Grand Bahama Intl
Mon 1/18
10:45 am-12:50 am
1 stop15h 05m
$496
Quickest round-trip
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 12/5
8:15 am-2:34 pm
1 stop5h 19m
Freeport Grand Bahama Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$573
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sun 3/28
8:25 am-1:30 pm
1 stop28h 05m
Freeport Grand Bahama Intl
Sat 4/3
10:45 am-10:19 pm
1 stop12h 34m
$654
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Fri 11/20
9:20 pm-1:30 pm
2 stops15h 10m
Freeport Grand Bahama Intl
Wed 11/25
10:45 am-11:34 pm
1 stop13h 49m
$769
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sat 12/19
8:59 am-11:50 am
1 stop25h 51m
Freeport Grand Bahama Intl
Sun 12/27
10:45 am-12:00 pm
2 stops26h 15m
$850
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Sun 12/27
5:59 pm-12:05 pm
2 stops17h 06m
Freeport Grand Bahama Intl
Wed 12/30
10:45 am-10:47 pm
2 stops13h 02m
$861
ChicagoFreeport
ORD Chicago O'Hare Intl - FPO Freeport Grand Bahama Intl
ORDFPO
Chicago O'Hare Intl
Wed 3/24
5:14 am-11:16 am
1 stop5h 02m
Freeport Grand Bahama Intl
Tue 3/30
11:56 am-7:59 pm
1 stop9h 03m
$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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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
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 November 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.
Boarding
7.4
Crew
7.9
Entertainment
6.8
Food
6.4
Comfort
7.2
Overall
7.0
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.4
Crew
7.9
Entertainment
6.8
Food
6.4
Comfort
7.2
Overall
7.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Freeport flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Freeport
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Freeport by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Freeport by cabin class
Find flights from Chicago to Freeport, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 November 10, 2026.
Chicago and Freeport flights
Browse other Chicago and Freeport flight options. Last updated on November 10, 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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$600 | Average$768 | FlexibilityNo cancel fee | On-time71% |