Cheap flights from Cleveland to Chicago

One-way fares from $150 · CLE → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Cleveland
Cheapest fare
$150

Frontier Airlines · Mon, Nov 16

Cheapest month
November

from $150

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 59m

490 km

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Cheapest month to fly from Cleveland to Chicago

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

  1. November 2026 Cheapest $150

Cheapest dates in November 2026

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

Frontier Airlines
Depart07:18 Mon, Nov 16CLE → ORD 6h 30m · 1 stop
$150one way, per person
View deal
Frontier Airlines
Depart16:50 Tue, Nov 3CLE → ORD 5h 59m · 1 stop
$171one way, per person
View deal
See every date in November 2026 →

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Getting around

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About flights from Cleveland to Chicago

Cleveland (CLE) and Chicago (CHI) are about 490 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 5h 59m. Over the next few months, one-way fares start from $150, 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 Cleveland to Chicago?

The cheapest one-way fare we've seen recently is $150 with Frontier Airlines, departing Monday, November 16, 2026.

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

November 2026 currently has the lowest fares, from $150 one way.

Are there direct flights from Cleveland to Chicago?

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

How long is the flight from Cleveland to Chicago?

The quickest journey we've seen takes about 5h 59m. Cleveland and Chicago are around 490 km apart.

Which airlines fly from Cleveland to Chicago?

Recent fares on this route were with Frontier Airlines.

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