Cheap flights from Wyoming to Chicago from $156

The month of February is, on average, the cheapest month to fly to Chicago from Wyoming, with most prices found around $370. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Wyoming to Chicago during October average around $378.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $554. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Wyoming to Chicago for around $875.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Wyoming to Chicago during this time can be as low as $533. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $623.

Fly from Jackson Hole to Chicago O'Hare Intl for the best Wyoming - Chicago flight prices

There are 4 cabin classes available to choose from on Wyoming to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 19% on your flight if you consider stops on a Wyoming to Chicago flight.

As of September 2026, 6 flights take off from Wyoming and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 64% of daily flights taking off in the afternoon.

As of September 2026, there are 47 flights per week flying from Wyoming to Chicago. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.