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Cheapest Time to Fly to Chicago

Save money when you take a trip to Chicago by booking your flights at the best time. Select your tickets at the right point before your departure and you could make considerable savings.

Here at Skyscanner we’ve crunched our numbers from 2018 to try to provide you the best possible information we can to help you save on your travel to Chicago in 2019.We’ve looked into information such as how many weeks in advance to book, the cheapest month to book flights, when to travel for the best savings, and when to book from specific origin cities. Take a look at our findings below:

Best time to book flights from the US

Cheapest Time to Fly to Chicago

Flexible on when you can fly to Chicago? We’ve looked into 2018 data to recommend the best months to travel to optimize your savings:

  • Travel in February for up to 25% savings, and in April for almost 6% off the average yearly flight price
  • Avoid visiting Chicago in July, where flight prices increase by up to 14% compared to the average

The Cheapest Month to Book Flights to Chicago

  • Flights booked in January and February are estimated to be the cheapest in 2019, with April and December being the next best options
  • Avoid booking in June, where prices are the highest compared to the rest of the year
Best time to book flights to Chicago

How Many Months in Advance to Book Your Flight

  • Book 3 months in advance where flights averaged $220 round-trip in 2018, compared to the week before travel where prices increased to as much as $350

Best Time to Book Flights to Chicago from Popular Cities

Below is a breakdown of the estimated best time to book for popular routes to Chicago based on historical data:

Departure FromBest Time To Book To ChicagoCheapest month to travel
Miami4 months in advanceFebruary
New York5 months in advanceFebruary
Los Angeles5 months in advanceFebruary
Atlanta3 months in advanceJanuary/February
San Francisco3 months in advanceJanuary
Orlando5 months in advanceApril/September
Ciudades en las que se grabó Sense8: Chicago
Chicago Skyline

Chicago is an increasingly popular destination in the United States. The Windy City features a distinctive skyline, bustling commercial neighborhoods, cultural centers, beautiful open spaces and a thriving food scene. Popular attractions in Chicago include Navy Pier, Millennium, the Art Institute of Chicago and the Willis Tower. Plan your travel to Chicago at the right time and you will be able to find the best airfares available.

Skyscanner has worked to help you find the cheapest time to fly to Chicago and increase your chances of securing the cheapest prices on air travel. This includes the use of our cheapest month search feature, our search everywhere tool and the ability to set up price alerts. Simple, painless, and saves travelers a lot of time + money while planning for your next trip!

Skyscanner App Reviews & Ratings

Check out App reviews and ratings and see why Skyscanner is the number one trusted travel app to search for flights, hotels and car rentals.  

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