Cheap flights from Cheyenne to Chicago

One-way fares from $357 · CYS → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Cheyenne
Cheapest fare
$357

United Airlines · Mon, Nov 9

Cheapest month
November

from $357

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 42m

1,430 km

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Cheapest month to fly from Cheyenne to Chicago

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

  1. November 2026 Cheapest $357

Cheapest dates in November 2026

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

United Airlines
Depart13:49 Mon, Nov 9CYS → ORD 3h 42m · 1 stop
$357one way, per person
View deal
See every date in November 2026 →

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About flights from Cheyenne to Chicago

Cheyenne (CYS) and Chicago (CHI) are about 1,430 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 42m. Over the next few months, one-way fares start from $357, 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 Cheyenne to Chicago?

The cheapest one-way fare we've seen recently is $357 with United Airlines, departing Monday, November 9, 2026.

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

November 2026 currently has the lowest fares, from $357 one way.

Are there direct flights from Cheyenne to Chicago?

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

How long is the flight from Cheyenne to Chicago?

The quickest journey we've seen takes about 3h 42m. Cheyenne and Chicago are around 1,430 km apart.

Which airlines fly from Cheyenne to Chicago?

Recent fares on this route were with United Airlines.

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