CHI - FPO

$212 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 5/7. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$446
Typical prices: $586-$718
Multiple Airlines
Sun 5/10Sat 5/16
ORD - FPO • 1 stop
Cheapest one-way
$212
Multiple Airlines
Thu 5/7
ORD - FPO • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Freeport. You'll need at least 1 connection.
Insights
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Top layover airports
Miami (MIA)
Cheapest • Avg $586 (round-trip)
Charlotte (CLT)
Shortest trip • 5h 05m (one-way)
Insights
Insights
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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

Sun, May 10 - Sat, May 16
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
FPO
7h 25m
1 stop
Multiple Airlines Logo
10:45 am - 9:17 pm
FPO
-
ORD
11h 32m
1 stop
$446Multiple Airlines
Sat, May 2 - Tue, May 5
Multiple Airlines Logo
1:27 pm - 1:30 pm
ORD
-
FPO
23h 03m
1 stop
Multiple Airlines Logo
10:45 am - 9:31 am
FPO
-
ORD
23h 46m
1 stop
$448Multiple Airlines
Fri, Apr 10 - Wed, Apr 15
Multiple Airlines Logo
5:05 am - 11:50 am
ORD
-
FPO
5h 45m
1 stop
Multiple Airlines Logo
10:45 am - 9:17 pm
FPO
-
ORD
11h 32m
1 stop
$449Multiple Airlines
Fri, May 8 - Thu, May 14
Multiple Airlines Logo
4:05 pm - 1:30 pm
ORD
-
FPO
20h 25m
1 stop
Multiple Airlines Logo
10:45 am - 10:59 pm
FPO
-
ORD
13h 14m
1 stop
$454Multiple Airlines
Sun, May 10 - Sat, May 16
Multiple Airlines Logo
7:45 pm - 1:30 pm
ORD
-
FPO
16h 45m
1 stop
Multiple Airlines Logo
10:45 am - 9:31 am
FPO
-
ORD
23h 46m
1 stop
$461Multiple Airlines
Fri, Apr 10 - Wed, Apr 15
Multiple Airlines Logo
7:17 am - 6:15 pm
ORD
-
FPO
9h 58m
2 stops
Multiple Airlines Logo
10:45 am - 9:17 pm
FPO
-
ORD
11h 32m
1 stop
$468Multiple Airlines
Tue, Apr 28 - Tue, May 5
Multiple Airlines Logo
7:15 pm - 1:30 pm
ORD
-
FPO
17h 15m
1 stop
Multiple Airlines Logo
10:45 am - 7:55 am
FPO
-
ORD
22h 10m
2 stops
$469Multiple Airlines
Thu, Apr 9 - Thu, Apr 23
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
FPO
7h 25m
1 stop
Multiple Airlines Logo
10:45 am - 12:24 am
FPO
-
ORD
14h 39m
1 stop
$474Multiple Airlines
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
6:10 pm - 11:50 am
ORD
-
FPO
16h 40m
1 stop
Multiple Airlines Logo
10:45 am - 10:54 pm
FPO
-
ORD
13h 09m
1 stop
$475Multiple Airlines
Thu, May 7 - Wed, May 13
Multiple Airlines Logo
3:05 pm - 1:30 pm
ORD
-
FPO
21h 25m
1 stop
Multiple Airlines Logo
10:45 am - 12:24 am
FPO
-
ORD
14h 39m
1 stop
$476Multiple 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.

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 – 78% 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 Charlotte (CLT) for the shortest journey. The average one-way travel time for flights connecting there is 5h 05m.

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, Charlotte (CLT) often has the shortest layovers from Chicago to Freeport, with an average of 1h 28m.

Find deals

Good to know

Low seasonOctober
Cheapest flight$212
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 9% 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 $212 for a one-way ticket and $446 for a round-trip.

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

    Yes

  • 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.
7.1
American AirlinesOverall score based on 11467 reviews
7.2Comfort
7.5Boarding
6.9Entertainment
6.4Food
7.9Crew
Airline reviews

The gate got changed several times and the flight was delayed over an hour. Awful experience

2.0 MediocreGenesis, Mar 2026
ORD - SDF
Read more American Airlines reviews

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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.

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

Information on your arrival and departure airports

Freeport (FPO)