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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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

Thu, Sep 11 - Mon, Sep 15
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5:05 am - 1:45 pmORD-FPO
7h 40m1 stop
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10:45 am - 5:39 pmFPO-ORD
7h 54m1 stop
Thu, Sep 11 - Mon, Sep 15
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8:56 pm - 1:45 pmORD-FPO
15h 49m2 stops
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10:45 am - 5:39 pmFPO-ORD
7h 54m1 stop
Fri, Dec 12 - Mon, Dec 15
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5:59 pm - 1:30 pmORD-FPO
18h 31m1 stop
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10:45 am - 9:00 pmFPO-ORD
11h 15m1 stop
Thu, Aug 28 - Tue, Sep 2
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5:05 am - 2:45 pmORD-FPO
8h 40m1 stop
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11:00 am - 11:59 pmFPO-ORD
13h 59m1 stop
Fri, Dec 12 - Mon, Dec 15
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8:30 pm - 1:30 pmORD-FPO
16h 00m2 stops
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10:45 am - 9:00 pmFPO-ORD
11h 15m1 stop
Fri, Dec 5 - Fri, Dec 12
American Airlines Logo
6:35 pm - 12:00 pmORD-FPO
16h 25m1 stop
American Airlines Logo
6:35 pm - 11:56 pmFPO-ORD
6h 21m1 stop
$587American Airlines
Find Deal
Fri, Dec 5 - Fri, Dec 12
American Airlines Logo
6:35 pm - 12:00 pmORD-FPO
16h 25m1 stop
American Airlines Logo
1:05 pm - 10:45 pmFPO-ORD
10h 40m2 stops
$591American Airlines
Find Deal
Sun, Feb 1 - Sun, Feb 8
American Airlines Logo
7:04 am - 4:25 pmORD-FPO
8h 21m1 stop
American Airlines Logo
6:59 pm - 8:59 amFPO-ORD
15h 00m1 stop
$592American Airlines
Find Deal
Sun, Feb 1 - Sun, Feb 8
American Airlines Logo
6:00 am - 4:25 pmORD-FPO
9h 25m2 stops
American Airlines Logo
1:00 pm - 9:54 pmFPO-ORD
9h 54m1 stop
$596American Airlines
Find Deal
Thu, Aug 28 - Tue, Sep 2
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5:05 am - 2:45 pmORD-FPO
8h 40m1 stop
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11:00 am - 10:26 amFPO-ORD
24h 26m2 stops
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.

What is the most popular layover airport when flying from Chicago to Freeport?

Percentage of 1-stop round-trip flights from Chicago to Freeport chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Miami (MIA) is the top choice – 89% of KAYAK users who clicked on 1-stop flights from Chicago to Freeport picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Freeport?

Average round-trip price for 1-stop flights from Chicago to Freeport clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Miami (MIA) offer the most affordable fares, with an average round-trip price of $586.

Which layover airport offers the shortest total travel time from Chicago to Freeport?

Shortest average total travel time for 1-stop one-way flights from Chicago to Freeport via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Fort Lauderdale (FLL) for the shortest journey. The average one-way travel time for flights connecting there is 4h 50m.

Which layover airport has the quickest connection when flying from Chicago to Freeport?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Freeport, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Fort Lauderdale (FLL) often has the shortest layovers from Chicago to Freeport, with an average of 1h 13m.

Good to know

Low seasonOctober
Cheapest flight$222
Best time to beat the crowds with an average 68% drop in price.
Most popular time to fly with an average 55% 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 $440 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
8.0Crew
7.5Boarding
6.5Food
6.9Entertainment
7.2Comfort
Airline reviews

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

2.0 MediocreAnonymous, Jul 2025ORD - RIC
Read more American Airlines reviews

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

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.

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

Information on your arrival and departure airports

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