Cheap flights from Jacksonville to Chicago

One-way fares from $147 · JAX → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Jacksonville
Cheapest fare
$147

Frontier Airlines · Fri, Jan 1

Cheapest month
January

from $147

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 23m

1,390 km

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Cheapest month to fly from Jacksonville to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 $177
  2. January 2027 Cheapest $147

Cheapest dates in January 2027

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart14:55 Fri, Jan 1JAX → ORD 3h 52m · 1 stop
$147one way, per person
View deal
jetBlue
Depart16:20 Tue, Jan 5JAX → ORD 5h 01m · 1 stop
$155one way, per person
View deal
See every date in January 2027 →

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About flights from Jacksonville to Chicago

Jacksonville (JAX) and Chicago (CHI) are about 1,390 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 3h 23m. Over the next few months, one-way fares start from $147, and January 2027 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Jacksonville to Chicago?

The cheapest one-way fare we've seen recently is $147 with Frontier Airlines, departing Friday, January 1, 2027. Over the coming months, the lowest fare in each month ranges from $147 to $177.

What is the cheapest month to fly from Jacksonville to Chicago?

January 2027 currently has the lowest fares, from $147 one way.

Are there direct flights from Jacksonville to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Jacksonville to Chicago?

The quickest journey we've seen takes about 3h 23m. Jacksonville and Chicago are around 1,390 km apart.

Which airlines fly from Jacksonville to Chicago?

Recent fares on this route were with Frontier Airlines and jetBlue.

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