Cheap flights from Montana to Chicago from $93

The month of January is, on average, the cheapest month to fly to Chicago from Montana, with most prices found around $230. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Montana to Chicago during September average around $230.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $421. 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 Montana to Chicago for around $583.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Montana to Chicago during this time can be as low as $377. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $476.

Fly from Bozeman Gallatin Field to Chicago O'Hare Intl for the best Montana - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Montana when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $360 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Montana for as low as $202 on momondo.

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

United Airlines, Southwest, and Delta are the most popular carriers operating from Montana to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Montana according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of February 2026, there are 8 flights per day flying from Montana to Chicago. The most common time of day flights depart is 12:00PM, with 62% of flights taking off in the afternoon.

The number of flights available between Montana and Chicago is 60 per week as of February 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.