Cheap flights from Islip to Chicago

One-way fares from $239 · ISP → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Islip
Cheapest fare
$239

Frontier Airlines · Sat, Nov 7

Cheapest month
November

from $239

Direct flights
Not recently

Usually 1+ stop

Quickest trip
6h 17m

1,220 km

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Cheapest month to fly from Islip to Chicago

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

  1. November 2026 Cheapest $239
  2. December 2026 $563

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About flights from Islip to Chicago

Islip (ISP) and Chicago (CHI) are about 1,220 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 6h 17m. Over the next few months, one-way fares start from $239, 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 Islip to Chicago?

The cheapest one-way fare we've seen recently is $239 with Frontier Airlines, departing Saturday, November 7, 2026. Over the coming months, the lowest fare in each month ranges from $239 to $563.

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

November 2026 currently has the lowest fares, from $239 one way.

Are there direct flights from Islip to Chicago?

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

How long is the flight from Islip to Chicago?

The quickest journey we've seen takes about 6h 17m. Islip and Chicago are around 1,220 km apart.

Which airlines fly from Islip to Chicago?

Recent fares on this route were with Frontier Airlines.

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