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Cheap Flights from Chicago to Freeport

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Compare Chicago to Freeport flight deals

Find the cheapest month or even day of the year to fly to Freeport

Book the best Freeport fare with no extra fees

Flight deals from Chicago to Freeport

Looking for a cheap last-minute deal or the best return flight from Chicago to Freeport? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Freeport

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Freeport flights are currently cheapest in April.
Apr
from £348
May
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Jun
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Jul
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Aug
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Sep
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Oct
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Chicago to Freeport: Alternative routes

Compare routes from Chicago to Freeport below. You may find an airport to fly into that's cheaper, faster, or easier than Freeport.

Chicago to Freeport: Flight information

The things to know before you go.
Cheapest flight found£348
Cheapest month to flyApril

Finding cheap flights from Chicago to Freeport: Frequently asked questions

The best price we found for a return flight from Chicago to Freeport is £356. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Freeport. But we found flights with one stop from £356.
As of April 2025, there are no flights flying from Chicago to Freeport.
The cheapest month to fly from Chicago to Freeport is usually April 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Freeport Airport on Saturday, 8 November 2025.
No airlines currently offer direct flights between Chicago and Freeport Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Freeport but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Freeport is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Freeport is Spirit Airlines .

How to find cheap flights to Freeport from Chicago

Looking for cheap tickets from Chicago to Freeport? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago to Freeport. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Freeport from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best Chicago-Freeport ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Freeport from Chicago.
  • Set up a Price Alert. You can easily track the fare of your cheap Chicago-Freeport flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Chicago and Freeport? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Chicago and Freeport. We scour the internet for the best Business, Premium Economy and First Class flight fares to Freeport, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Chicago to Freeport flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

    • Combine your flight to Freeport from Chicago with hotels and car hire

    Once you've secured your cheap flight ticket from Chicago to Freeport, discover the best prices and exclusive rates for hotels in Freeport or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


Plan the rest of your trip from Chicago to Freeport

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.