CHI - FPO

$200 Find Cheap Flights from Chicago to Freeport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Freeport departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Freeport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Freeport, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Freeport, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$428
Overall average: $907
Multiple Airlines
Wed 4/15Tue 4/21
ORD - FPO • 1 stop
Cheapest one-way
$200
Multiple Airlines
Thu 4/16
ORD - FPO • 1 stop
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We hope you love your trip to Freeport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Freeport (CHI-FPO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Freeport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Freeport

Wed, Apr 15 - Tue, Apr 21
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
FPO
7h 15m
1 stop
Multiple Airlines Logo
10:45 am - 9:17 pm
FPO
-
ORD
11h 32m
1 stop
$428Multiple Airlines
Sat, May 16 - Sat, May 23
Multiple Airlines Logo
1:27 pm - 1:30 pm
ORD
-
FPO
23h 03m
1 stop
Multiple Airlines Logo
10:45 am - 11:41 pm
FPO
-
ORD
13h 56m
1 stop
$451Multiple Airlines
Tue, Mar 10 - Sun, Mar 15
Multiple Airlines Logo
6:36 pm - 1:30 pm
ORD
-
FPO
17h 54m
1 stop
Multiple Airlines Logo
10:45 am - 11:17 am
FPO
-
ORD
25h 32m
1 stop
$453Multiple Airlines
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
FPO
7h 15m
1 stop
Multiple Airlines Logo
10:45 am - 4:59 pm
FPO
-
ORD
7h 14m
1 stop
$469Multiple Airlines
Sun, Apr 19 - Fri, Apr 24
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
FPO
7h 15m
1 stop
Multiple Airlines Logo
10:45 am - 10:57 pm
FPO
-
ORD
13h 12m
1 stop
$477Multiple Airlines
Thu, Apr 2 - Thu, Apr 9
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
FPO
7h 25m
1 stop
Multiple Airlines Logo
10:45 am - 10:50 pm
FPO
-
ORD
13h 05m
1 stop
$486Multiple Airlines
Tue, Mar 10 - Sun, Mar 15
Multiple Airlines Logo
8:42 pm - 1:30 pm
ORD
-
FPO
15h 48m
2 stops
Multiple Airlines Logo
10:45 am - 11:17 am
FPO
-
ORD
25h 32m
1 stop
$490Multiple Airlines
Sat, May 23 - Sat, May 30
Multiple Airlines Logo
5:32 pm - 1:30 pm
ORD
-
FPO
18h 58m
1 stop
Multiple Airlines Logo
10:45 am - 11:41 pm
FPO
-
ORD
13h 56m
1 stop
$495Multiple Airlines
Fri, Apr 17 - Mon, Apr 20
Multiple Airlines Logo
1:27 pm - 1:30 pm
ORD
-
FPO
23h 03m
1 stop
Multiple Airlines Logo
10:45 am - 6:40 pm
FPO
-
ORD
8h 55m
2 stops
$497Multiple Airlines
Wed, May 6 - Tue, May 12
Multiple Airlines Logo
1:27 pm - 1:30 pm
ORD
-
FPO
23h 03m
1 stop
Multiple Airlines Logo
9:30 am - 9:17 pm
FPO
-
ORD
12h 47m
1 stop
$500Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Freeport flights

Get data-powered insights and trends into flights from Chicago to Freeport to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Freeport, City of Freeport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Freeport, City of Freeport departing in April.
Find deals

Good to know

Low seasonOctober
Cheapest flight$200
Best time to beat the crowds with an average 51% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Freeport

When to book flights from Chicago to Freeport

Are your dates flexible? Find out the best times to travel from Chicago to Freeport based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Freeport

  • What is the cheapest flight from Chicago to Freeport?

    In the last 3 days, the lowest price for a flight from Chicago to Freeport was $200 for a one-way ticket and $428 for a round-trip.

  • Do I need a passport to fly between Chicago and Freeport?

    Yes

  • Which airports will I be using when flying from Chicago to Freeport?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Freeport Grand Bahama Intl.

  • Which aircraft models fly most regularly from Chicago to Freeport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Freeport?

    oneworld is the only airline alliance operating flights between Chicago and Freeport.

  • How does KAYAK find such low prices on flights from Chicago to Freeport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Freeport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Freeport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Freeport from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Freeport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Freeport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Freeport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Freeport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Freeport

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Freeport. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Freeport? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11267 reviews
6.4Food
7.5Boarding
7.2Comfort
8.0Crew
6.9Entertainment
Airline reviews

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

2.0 MediocreAndrew, Feb 2026
ORD - LGA
Read more American Airlines reviews

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

Everything you need to know for your flight from Chicago to Freeport

Information on your arrival and departure airports

Freeport (FPO)