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Cheap Flights from Jacksonville to Chicago

Popular airlines from Jacksonville to Chicago

You can choose from 1 airlines that fly from Jacksonville to Chicago, including United Airlines, American Airlines offers the lowest prices on this route.
United Airlines logo United Airlines
Airlines are determined based on actual purchased flight tickets from Jacksonville to Chicago according to previous 12 months data from Trip.com.

Explore the cheapest flights from Jacksonville to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way direct flights start at S$ 156, and round-trip direct tickets start at S$ 306.

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flying from Jacksonville to Chicago

The distance between Jacksonville and Chicago is approximately 1,382.54km. It takes around 2 hours 48 minutes on average to fly from Jacksonville to Chicago. Based on Trip.com's data, travel demand peaks in July. The off-season for travel is October.

Cheapest one-way flight priceS$ 110
Cheapest return ticket priceS$ 268
Off-season for travelOctober
Peak season for travelJuly
Flight distance1,382.54km
Average flight time2 hours 48 minutes
Popular airlineUnited Airlines
Flight statistics for the Jacksonville–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Jacksonville (JAX) to Chicago (CHI)?

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as S$ 110 on Cheapest nonstop routes (e.g. JAX to MDW on Sat, May 2), while American Airlines offers Cheapest nonstop round-trips from S$ 268 departing on Tue, Apr 28 and returning on Tue, May 5.
  • At the moment, you can catch a direct flight from Jacksonville to Chicago with the following airlines, including: United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 2 hours 48 minutes to fly from Jacksonville (JAX) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Jacksonville to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 36 flight per week flying from Jacksonville to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA411 (07:46)
  • To find best deals on flights from Jacksonville to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, May 2, with one-way flights priced at just S$ 110.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Jacksonville to Chicago is October, when demand for travel is lower.
  • After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Jacksonville to Chicago on March 19, 2026 with Frontier Airlines, with prices starting at S$ 141.
  • You can land at any one of the following hubs in Chicago, with Jacksonville International Airport to O'Hare International Airport (JAX-ORD) is by far the most common option on this route: O'Hare International Airport (ORD) Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Jacksonville is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.