CHI - FPO

$222 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 10/20. 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

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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Flights 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, Aug 13 - Wed, Aug 20
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11:28 am - 12:25 pmORD-FPO
23h 57m1 stop
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11:00 am - 7:07 pmFPO-ORD
9h 07m1 stop
Thu, Aug 14 - Thu, Aug 21
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8:12 pm - 4:50 pmORD-FPO
19h 38m1 stop
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11:00 am - 7:07 pmFPO-ORD
9h 07m1 stop
Thu, Aug 14 - Thu, Aug 21
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5:05 am - 1:45 pmORD-FPO
7h 40m1 stop
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11:00 am - 11:59 pmFPO-ORD
13h 59m1 stop
Wed, Aug 20 - Wed, Aug 27
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5:05 am - 1:45 pmORD-FPO
7h 40m1 stop
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11:00 am - 7:07 pmFPO-ORD
9h 07m1 stop
Sat, Aug 2 - Tue, Aug 5
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5:05 am - 1:45 pmORD-FPO
7h 40m1 stop
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11:00 am - 11:13 pmFPO-ORD
13h 13m1 stop
Thu, Aug 14 - Thu, Aug 21
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8:47 pm - 4:50 pmORD-FPO
19h 03m2 stops
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11:00 am - 11:59 pmFPO-ORD
13h 59m1 stop
Thu, Aug 14 - Thu, Aug 21
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6:49 pm - 4:50 pmORD-FPO
21h 01m2 stops
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11:00 am - 11:59 pmFPO-ORD
13h 59m1 stop
Wed, Aug 6 - Sun, Aug 10
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5:05 am - 1:45 pmORD-FPO
7h 40m1 stop
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5:45 pm - 8:55 amFPO-ORD
16h 10m1 stop
Wed, Aug 20 - Wed, Aug 27
American Airlines Logo
8:41 pm - 9:41 amORD-FPO
12h 00m2 stops
American Airlines Logo
10:21 am - 6:29 pmFPO-ORD
9h 08m2 stops
$589American Airlines
Find Deal
Fri, Dec 5 - Fri, Dec 12
American Airlines Logo
6:00 am - 4:25 pmORD-FPO
9h 25m2 stops
American Airlines Logo
6:35 pm - 9:03 amFPO-ORD
15h 28m1 stop
$591American Airlines
Find Deal
Useful Info

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?

What is the cheapest month to fly from Chicago to Freeport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Freeport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Freeport is October, where tickets cost $288 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $993 and $808 respectively.

Good to know

Low seasonOctober
High seasonJuly
Cheapest flight$222
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 7% 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 $222 for a one-way ticket and $471 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 10000 reviews
7.2Comfort
8.0Crew
7.5Boarding
6.9Entertainment
6.5Food
Airline reviews

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

10.0 ExcellentNicholas, Jun 2025ORD - BOS
Read more American Airlines reviews

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

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

Information on your arrival and departure airports

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