Cheap flights from Des Moines to Chicago from $96

The month of February is, on average, the cheapest month to fly to Chicago from Des Moines, with most prices found around $239. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Des Moines to Chicago during December average around $253.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $514. 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 Des Moines to Chicago for around $691.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Des Moines to Chicago during this time can be as low as $509. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,088.

Fly from Des Moines to Chicago Midway for the best Des Moines - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Des Moines when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $347 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Des Moines for as low as $199 on momondo.

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

No. A direct flight is the cheapest option for a flight between Des Moines to Chicago.

As of October 2026, prices for Des Moines to Chicago flights are approximately 59% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Des Moines according to our data. United Airlines is the first choice among our users, with 67% 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.

The number of flights available between Des Moines and Chicago is 21 per day as of October 2026. The most frequent departure time is 2:00PM, with 49% of daily flights leaving at noon.

As of October 2026, 148 flights take off from Des Moines and land in Chicago each week. The most common flight departure day for this route is Thu, with 30% of weekly flights taking off on this day.