Cheap flights from Chicago to Wyoming from $100

The cheapest month to fly to Wyoming from Chicago is in September. Flight prices, which tend to average around $191, are often lower during this time because this is during the off-season. If you aren’t able to travel to Wyoming during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $229.

The cheapest day to depart from Chicago to Wyoming is on a Monday. Travelers who choose to depart for Wyoming on a Monday will often find tickets for as low as $425. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Wyoming for around $527.

Our most recent data shows that the best time of day to fly to Wyoming is at noon. Flights from Chicago to Wyoming during this time can be as low as $425. In the morning is when there is more demand to fly to Wyoming, so prices are often more expensive at around $482 per ticket.

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

You are more likely to see cheaper flights to Wyoming from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Wyoming for around $435 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Wyoming from Chicago for as low as $378 on momondo.

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

As of June 2026, there are 106 flights per day flying from Chicago to Wyoming. The most common time of day flights depart is 9:00AM, with 52% of flights taking off in the afternoon.

743 flights are operational weekly from Chicago to Wyoming as of June 2026. The most popular departure day for this route is Sun, with 16% of flights per week taking off on this day.