Cheap flights from Des Moines to Chicago from $119

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 October is your next best option. Flight prices from Des Moines to Chicago during October average around $242.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $501. 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 $673.

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 $493. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,017.

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 $315 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.

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

As of August 2026, prices for Des Moines to Chicago flights are approximately 2% more expensive when compared to flights at the same time last year.

The number of flights available between Des Moines and Chicago is 41 per day as of August 2026. The most frequent departure time is 1:00PM, with 54% of daily flights leaving at noon.

As of August 2026, 289 flights take off from Des Moines and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.