Cheap Flights from Des Moines to Chicago Midway

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Flight deals from Des Moines to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Des Moines Airport to Chicago Midway Airport? If you want to travel next month, return fares start from Rs69,411. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Des Moines to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Des Moines to Chicago Midway flights are currently cheapest in July.

Direct flights from Des Moines to Chicago Midway

Des Moines to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs34,395
Cheapest month to flyJuly
Average flight time1 hr, 21 mins
Most popular airlineSouthwest Airlines
Average flights per week14

Finding cheap flights from Des Moines to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Des Moines to Chicago Midway is Rs68,789. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 21 minutes is the average flight time from Des Moines to Chicago Midway.
Southwest Airlines flies direct from Des Moines to Chicago Midway.
As of June 2026, there are 14 flights per week flying from Des Moines to Chicago Midway.
The cheapest month to fly from Des Moines to Chicago Midway is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Des Moines Airport to Chicago Midway Airport on Tuesday, 27 October 2026.
Yes – the average flight time is 1 hour and 21 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Des Moines Airport (DSM) to Chicago Midway Airport (MDW): what you need to know

  • The average time for a direct flight from Des Moines Airport to Chicago Midway Airport is 1 hour 20 minutes.

  • Chicago's timezone is UTC-6, which is the same as Des Moines.

  • Every week, there are eight Des Moines Airport to Chicago Midway Airport flights.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your DSM to MDW flight.

  • Be prepared for longer queues during popular months such as August. Arriving up to four hours in advance for an international flight and two hours for domestic departures will give you ample time for security and boarding.

  • Southwest Airlines offers direct flights from Des Moines Airport to Chicago Midway Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of the United States if time allows.

  • Most passengers choose to travel with Southwest Airlines on this route.

  • Consider adding a stopover when booking your ticket from Des Moines Airport to Chicago Midway Airport. Simply uncheck 'Direct flights only' to break up your trip, or visit a new city along the way. Check out these options between DSM and MDW:

    • Denver International Airport

    • Detroit Wayne County Airport

    • Minneapolis St Paul Airport

How to find the cheapest flights from Des Moines Airport (DSM) to Chicago Midway Airport (MDW)

  • The lowest price we've seen for a one-way Des Moines Airport to Chicago Midway Airport flight is Rs34,395. A return fare is currently Rs68,789. Depending on the availability when you book, these fares could change.

  • Don't leave everything to the last minute. You're more likely to find cheap tickets from DSM to MDW if you book ahead. Airlines often offer some amazing early bird deals.

  • Getting cheap flights from Des Moines Airport to Chicago Midway Airport is easy if you're flexible with your trip dates. Use the 'Whole month' search tool to see the lowest prices throughout the month and land a great deal.

  • You won't have to check back in every day to find out if fares have gone down when you create a Price Alert. We'll update you the moment a special offer becomes available on cheap flights from DSM to MDW.

  • Tailor your flights with filters. Pick your arrival and departure times, total journey duration and airlines. You can also sort results by 'Cheapest,' 'Fastest' or 'Best' flights from Des Moines Airport to Chicago Midway Airport.

Handy information about Des Moines Airport (DSM)

  • You'll find DSM at 5800 Fleur Drive, Suite 201.

  • When it comes to the on-time performance of Des Moines Airport, 77% of flights meet their scheduled arrival time.

  • Central Des Moines to Des Moines Airport is approximately 11 kilometres. Depending on traffic, it'll take you about 15 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • Taking public transport? Expect a journey time of around 30 minutes.

  • Get your break off to a relaxed start by staying near DSM. Whether you've booked an early flight from Des Moines Airport to Chicago Midway Airport or want to avoid feeling rushed, these stays are the answer:

Arriving at Chicago Midway Airport (MDW)

Getting from Chicago Midway Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway Airport to the centre of Chicago has a drive time of about 25 minutes. It's approximately 16 kilometres away.

  • Getting to the centre by public transport will take you roughly 30 minutes.

When to fly to Chicago Midway Airport (MDW)

  • It's time to choose your travel dates for your flight from Des Moines Airport to Chicago Midway Airport. July is the busiest month to head to Chicago. If you want a more low-key vibe, go in December.

  • Before locking in your flight from Des Moines Airport to Chicago Midway Airport, consider the type of weather you like. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.

  • If you'd rather travel in cooler conditions, look for a cheap ticket from DSM to MDW in January. Temperatures average between -12ºC and 3ºC then.

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be discovered once you've seen Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in the United States. Experience this destination's highlights firsthand at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.