Cheap flights from Chicago to Freeport

Flights overview

Useful information for finding cheap flights from Chicago to Freeport and booking your next trip
Cheapest round-trip flights $177
JetBlue Nonstop 3 hr Thu, Jul 23 — Sun, Jul 26
The cheapest round-trip flight from Chicago to Freeport is currently $177
Cheapest one-way flight $89
American Nonstop 3 hr Wed, Jul 1
The cheapest one-way flight from Chicago to Freeport is currently $89
Last-minute weekend getaway $267
American 1 stop 13 hr Sat, May 9 — Sun, May 10
The cheapest last-minute weekend getaway from Chicago to Freeport is currently $267
Cheapest business class flights $439
American Nonstop 3 hr Thu, May 28 — Sun, May 31
The cheapest business class round-trip flight from Chicago to Freeport is currently $439
Fastest flight 2 hr 14 min The fastest nonstop flight from Chicago to Freeport takes 2 hr 14 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Freeport is typically January. The most expensive month to fly is typically May.
January
Cheapest
Typical prices: $90–245
May
Most expensive
Typical prices: $185–240

Popular airlines from Chicago to Freeport

  • Delta
    Nonstop
    from $192
    Typical price: $180–435
    27 weekly nonstop flights
    ORD - JFK Every day
    1268 weekly connecting flights
    MDW, ORD - JFK Every day
  • American
    Nonstop
    from $192
    Typical price: $175–325
    21 weekly nonstop flights
    ORD - JFK Every day
    347 weekly connecting flights
    ORD - JFK Every day
  • JetBlue
    Nonstop
    from $177
    Typical price: $165–445
    7 weekly nonstop flights
    ORD - JFK Every day
    25 weekly connecting flights
    ORD - JFK Every day
  • Frontier
    Typical price: $120–340
    30 weekly connecting flights
    MDW, ORD - JFK Every day
  • Alaska
    from $660
    Typical price: $480–1,100
    21 weekly connecting flights
    ORD - JFK Every day
  • Sun Country Airlines
    Typical price: $385–670
    3 weekly connecting flights
    ORD - JFK Every Thu, Fri, Sun

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Freeport

  • John F. Kennedy International Airport (JFK)
    New York United States 28 min 10 mi
  • LaGuardia Airport (LGA)
    New York United States 38 min 17 mi
  • Newark Liberty International Airport (EWR)
    Newark United States 1 hr 10 min 30 mi
  • Philadelphia International Airport (PHL)
    Philadelphia United States 2 hr 19 min 103 mi

Frequently asked questions about flying from Chicago to Freeport

The cheapest flights from Chicago to Freeport are usually in January. Typical ticket prices in January range from $90 to $245.
The cheapest round-trip flight from Chicago to Freeport recently found on Google Flights was with JetBlue from $177. The cheapest one-way flight was with American from $89.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Delta flight from Chicago to Freeport is $192, flying from May 29 to May 31.
  • The cheapest American flight from Chicago to Freeport is $192, flying from May 28 to May 31.
  • The cheapest JetBlue flight from Chicago to Freeport is $177, flying from Jul 23 to Jul 26.
  • The cheapest Alaska flight from Chicago to Freeport is $660, flying from Jun 6 to Jun 8.
The cheapest round-trip flight from Chicago to Freeport starts at $177 from Thu, Jul 23 to Sun, Jul 26. The cheapest one-way flight starts at $89 and departs on Wed, Jul 1.
2 hr 14 min is the shortest flight time from Chicago to Freeport.
It's easy to use Google Flights to find the cheapest days to fly from Chicago to Freeport.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to Freeport really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Freeport.

In terms of nonstop flights, Delta is the most popular. Delta offers 27 nonstop flights and 1,268 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .

Other popular airlines flying from Chicago to Freeport are:
  • American offers 21 nonstop flights and 347 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .
  • JetBlue offers 7 nonstop flights and 25 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .
  • Frontier offers 30 connecting flights per week. Frontier flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .
  • Alaska offers 21 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .
  • Sun Country Airlines offers 3 connecting flights per week. Sun Country Airlines flies from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and Freeport.
The cheapest round-trip flight from Chicago to Freeport recently found on Google Flights was with JetBlue from $177. The cheapest one-way flight was with American from $89.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Delta flight from Chicago to Freeport is $192, flying from May 29 to May 31.
  • The cheapest American flight from Chicago to Freeport is $192, flying from May 28 to May 31.
  • The cheapest JetBlue flight from Chicago to Freeport is $177, flying from Jul 23 to Jul 26.
  • The cheapest Alaska flight from Chicago to Freeport is $660, flying from Jun 6 to Jun 8.
Delta, American and JetBlue fly direct from Chicago to Freeport.
  • There are 27 Delta direct flights from Chicago to Freeport per week. Flights are available every day.
  • There are 21 American direct flights from Chicago to Freeport per week. Flights are available every day.
  • There are 7 JetBlue direct flights from Chicago to Freeport per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and Freeport at price $267 is offered by American from Sat, May 9 to Sun, May 10.
Delta, American and JetBlue fly direct from Chicago to Freeport.
  • There are 27 Delta direct flights from Chicago to Freeport per week. Flights are available every day.
  • There are 21 American direct flights from Chicago to Freeport per week. Flights are available every day.
  • There are 7 JetBlue direct flights from Chicago to Freeport per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Chicago to Freeport on a daily basis.
The cheapest direct (nonstop) round-trip flights between Chicago and Freeport start at $177 from Thu, Jul 23 to Sun, Jul 26 with JetBlue.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Freeport, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and Freeport start at $439 from Thu, May 28 to Sun, May 31 with American.
The cheapest economy class round-trip flights between Chicago and Freeport start at $177 from Thu, Jul 23 to Sun, Jul 26.
To book business class trips from Chicago to Freeport, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and Freeport starts at $267 from Sat, May 9 to Sun, May 10 with American.
The cheapest last-minute deal between Chicago and Freeport at price $267 is offered by American from Sat, May 9 to Sun, May 10.
To find last-minute flight deals from Chicago to Freeport, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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