Cheap flights from Chicago to Cheyenne

One-way fares from $315 · CHI → CYS · prices found by travellers in the last 48 hours

Compare all dates Cheyenne → Chicago
Cheapest fare
$315

Frontier Airlines · Thu, Nov 12

Cheapest month
November

from $315

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 41m

1,430 km

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Cheapest month to fly from Chicago to Cheyenne

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

  1. November 2026 Cheapest $315

Cheapest dates in November 2026

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

Frontier Airlines
Depart10:29 Thu, Nov 12ORD → CYS 5h 56m · 2 stops
$315one way, per person
View deal
United Airlines
Depart15:56 Tue, Nov 10ORD → CYS 3h 41m · 1 stop
$325one way, per person
View deal
Frontier Airlines
Depart06:30 Fri, Nov 13ORD → CYS 3h 45m · 1 stop
$336one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Cheyenne

Where to stay, what to do and getting around, from our travel partners.

Where to stay

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Things to do

Things to do in CheyenneTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in CheyennePre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in CheyenneCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Cheyenne

Chicago (CHI) and Cheyenne (CYS) 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 41m. Over the next few months, one-way fares start from $315, 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 Chicago to Cheyenne?

The cheapest one-way fare we've seen recently is $315 with Frontier Airlines, departing Thursday, November 12, 2026.

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

November 2026 currently has the lowest fares, from $315 one way.

Are there direct flights from Chicago to Cheyenne?

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

How long is the flight from Chicago to Cheyenne?

The quickest journey we've seen takes about 3h 41m. Chicago and Cheyenne are around 1,430 km apart.

Which airlines fly from Chicago to Cheyenne?

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

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