Cheap flights from Billings to Chicago from $169

The month of February is, on average, the cheapest month to fly to Chicago from Billings, with most prices found around $279. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Billings to Chicago during January average around $290.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $407. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Billings to Chicago for around $724.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Billings to Chicago during this time can be as low as $505. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $583.

Fly from Billings Logan Intl to Chicago O'Hare Intl for the best Billings Logan Intl - Chicago flight prices

There are 4 cabin classes available to choose from on Billings 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 36% on your flight if you consider stops on a Billings to Chicago flight.

Delta and United Airlines are the most popular carriers operating from Billings Logan Intl to Chicago

United Airlines, Delta and American Airlines are the top three most popular airlines that fly to Chicago from Billings according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Dallas (DFW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Denver (DEN) offer the lowest average round-trip price of $306.

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 5h 15m.

Denver (DEN) has the shortest average layover time for this route: 1h 00m.

As of September 2026, there are 2 flights per day flying from Billings to Chicago. The most common time of day flights depart is 12:00PM, with 93% of flights taking off in the afternoon.

As of September 2026, there are 14 flights per week flying from Billings to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.