Cheap flights from Des Moines to Chicago from $48

The month of September is, on average, the cheapest month to fly to Chicago from Des Moines, with most prices found around $208. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Des Moines to Chicago during October average around $221.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $524. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Des Moines to Chicago for around $838.

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 $528. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,009.

Fly from Des Moines to Chicago O'Hare Intl 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 $249 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 $187 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.

You could potentially save up to 4% on your flight if you consider stops on a Des Moines to Chicago flight.

As of February 2026, prices for Des Moines to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.

The number of flights available between Des Moines and Chicago is 36 per day as of February 2026. The most frequent departure time is 10:00AM, with 51% of daily flights leaving at noon.

As of February 2026, 253 flights take off from Des Moines and land in Chicago each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.