Cheap flights from Charleston to Chicago

One-way fares from $288 · CRW → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Charleston
Cheapest fare
$288

American Airlines · Thu, Nov 12

Cheapest month
November

from $288

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 48m

640 km

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Cheapest month to fly from Charleston to Chicago

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

  1. November 2026 Cheapest $288

Cheapest dates in November 2026

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

American Airlines
Depart05:00 Thu, Nov 12CRW → ORD 3h 58m · 1 stop
$288one way, per person
View deal
American Airlines
Depart05:00 Fri, Nov 13CRW → ORD 3h 58m · 1 stop
$288one way, per person
View deal
See every date in November 2026 →

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About flights from Charleston to Chicago

Charleston (CRW) and Chicago (CHI) are about 640 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 48m. Over the next few months, one-way fares start from $288, and November 2026 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 Charleston to Chicago?

The cheapest one-way fare we've seen recently is $288 with American Airlines, departing Thursday, November 12, 2026.

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

November 2026 currently has the lowest fares, from $288 one way.

Are there direct flights from Charleston to Chicago?

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

How long is the flight from Charleston to Chicago?

The quickest journey we've seen takes about 3h 48m. Charleston and Chicago are around 640 km apart.

Which airlines fly from Charleston to Chicago?

Recent fares on this route were with American Airlines.

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