Cheap flights from Des Moines to Chicago from $103

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 $251.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $509. 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 $693.

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 $502. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,068.

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 $333 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 $189 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 1% on your flight if you consider stops on a Des Moines to Chicago flight.

As of September 2026, prices for Des Moines to Chicago flights are approximately 45% more expensive when compared to flights at the same time last year.

The number of flights available between Des Moines and Chicago is 35 per day as of September 2026. The most frequent departure time is 2:00PM, with 48% of daily flights leaving at noon.

As of September 2026, 247 flights take off from Des Moines and land in Chicago each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.