Cheap flights from Des Moines to Chicago

Compare Des Moines to Chicago flight deals

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Flight deals from Des Moines to Chicago

Looking for a cheap last-minute deal or the best return flight from Des Moines Airport to Chicago? If you want to travel next month, return fares start from P14,635. Find the lowest prices on one-way and return tickets right here.

Chicago.P5,771 per passenger.Departing Wed, 1 Jul.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Des Moines on Wed, 1 Jul, arriving in Chicago Rockford.Price includes taxes and charges.From P5,771, select.

Chicago.P6,520 per passenger.Departing Thu, 28 May.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Des Moines on Thu, 28 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P6,520, select.

Chicago.P6,995 per passenger.Departing Mon, 29 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Des Moines on Mon, 29 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From P6,995, select.

Chicago.P7,610 per passenger.Departing Fri, 21 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Des Moines on Fri, 21 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From P7,610, select.

Chicago.P7,818 per passenger.Departing Wed, 2 Sep.One-way flight with United.Outbound direct flight with United departs from Des Moines on Wed, 2 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From P7,818, select.

Chicago.P7,836 per passenger.Departing Wed, 15 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed, 15 Jul, arriving in Chicago Midway.Price includes taxes and charges.From P7,836, select.

Chicago.P7,854 per passenger.Departing Wed, 18 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From P7,854, select.

Chicago.P7,896 per passenger.Departing Tue, 23 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Tue, 23 Jun, arriving in Chicago Midway.Price includes taxes and charges.From P7,896, select.

Chicago.P7,911 per passenger.Departing Wed, 19 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed, 19 Aug, arriving in Chicago Midway.Price includes taxes and charges.From P7,911, select.

Chicago.P8,261 per passenger.Departing Sat, 10 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Sat, 10 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P8,261, select.

Chicago.P14,872 per passenger.Departing Fri, 29 May.One-way flight with United.Outbound direct flight with United departs from Des Moines on Fri, 29 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P14,872, select.

Chicago.P46,325 per passenger.Departing Fri, 16 Apr.One-way flight with United.Outbound direct flight with United departs from Des Moines on Fri, 16 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From P46,325, select.

Find the cheapest month to fly from Des Moines to Chicago

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

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Direct flights from Des Moines to Chicago

Alternative Des Moines to Chicago routes

Looking for the cheapest, fastest or easiest route from Des Moines to Chicago? You could fly into the following airports instead.

Des Moines to Chicago: Flight information

The things to know before you go.

Cheapest flight found	P5,769
Cheapest month to fly	July
Average flight time	1 hr, 32 mins
Most popular airline	American Airlines
Average flights per week	487

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

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Des Moines to Chicago?

The best price we found for a return flight from Des Moines to Chicago is P14,635. 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.

How long does it take to fly from Des Moines to Chicago?

1 hour and 31 minutes is the average flight time from Des Moines to Chicago.

Which airlines fly direct from Des Moines to Chicago?

American Airlines, Alaska Airlines and United fly direct from Des Moines to Chicago.

How many flights are there a week from Des Moines to Chicago?

As of May 2026, there are 487 flights per week flying from Des Moines to Chicago.

When is the cheapest time to fly from Des Moines to Chicago?

The cheapest month to fly from Des Moines to Chicago is usually June.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Des Moines Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from P14,635.

Which upcoming date is cheapest to fly from Des Moines Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Des Moines Airport to Chicago on Sunday, 14 June 2026.

Can I get a direct flight from Des Moines Airport to Chicago?

Yes – the average flight time is 1 hour and 31 minutes.

How can I get the best flight deal from Des Moines Airport to Chicago?

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 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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Des Moines Airport to Chicago with?

Currently, Allegiant Air and United offer the cheapest flight tickets to Chicago.

Flying from Des Moines International Airport (DSM) to Chicago: what you need to know

Around 1 hour 25 minutes is how long you'll be travelling on a direct flight from Des Moines International Airport to Chicago.
Des Moines (the location of Des Moines International Airport) and Chicago follow the same timezone — UTC-6.
The most popular route is from Des Moines International Airport (DSM) to Chicago O'Hare International Airport (ORD). There are 64 weekly services between these two airports. If you want to get on your way as soon as you can, the earliest flight from DSM to ORD is the 05:00 American Airlines service. If you prefer to travel later, the last departure is at 18:50 with United Airlines.
To avoid rushing for your DSM to Chicago flight, allow plenty of time for things like baggage drop and finding your gate. Arriving two hours before international departures and an hour before domestic flights is the general travel rule.
Flying over a peak time such as July? School holidays and other popular periods can mean longer queues and delays at security. Play it safe and get there up to four hours before an international flight and two hours before domestic departures.
Direct Des Moines International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll disembark.
Well-known airlines that offer direct flights from Des Moines International Airport to Chicago include:
DSM is about 6 kilometers from central Des Moines. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 15 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the journey time to be around 30 minutes.
Searching for a hotel near DSM? If you're catching an early flight from Des Moines International Airport to Chicago, these accommodation options will get you from your pillow to the plane in no time:
77% of flights taking off from Des Moines International Airport land at their destination on time.
DSM is located at 5800 Fleur Drive, Suite 201.

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

The best price we've found for a one-way Des Moines International Airport to Chicago flight is P5,769. The cheapest price for a return flight is P14,639. Remember fares may change due to demand at the time of booking.
Don't leave everything to the last minute. You're more likely to land cheap flights from DSM to Chicago if you book in advance. Airlines often have some great early bird discounts.
Landing cheap tickets from Des Moines International Airport to Chicago is more likely if you can be flexible with your dates. Try using the 'Whole month' search function to access the lowest prices across the month and score an epic deal.
You don't need to check back in every day to find out if fares have dropped when you create a Price Alert. We'll update you when there's an updated deal for cheap flights from DSM to Chicago.
Find an affordable flight from Des Moines International Airport to Chicago with the help of our filters. Select your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to the centre of Chicago takes about 30 minutes to reach by car. The centre is roughly 27 kilometers away.
Travelling to the centre on public transport takes about 45 minutes.
The last thing you want is a lengthy journey to your hotel if you're getting in late on a flight from Des Moines International Airport to Chicago. Check in to one of these accommodation options near ORD instead:
Reserving your ride from Chicago O'Hare International Airport about four weeks in advance of your flight from DSM to Chicago can help you get the best possible rate.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Des Moines International Airport to Chicago has hit the runway, you can reach the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometers from Chicago Midway International Airport (MDW).
If you travel by public transport, the ride to the centre takes 30 minutes or so.
Hang up the 'Do not disturb' sign and unwind at a hotel close to MDW. Here are a few options where you can tuck yourself in after your DSM to Chicago flight:
Call dibs on the best options. Securing your ride from MDW four weeks ahead of time often means more savings and a wider range of vehicles.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Make your way to the city centre after your flight from Des Moines International Airport to Chicago has touched down. Central Chicago is around 145 kilometers from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by taxi or ride-share.
Public transport will take you there in about 2 hours.
Enjoy a low-stress, comfortable start to your break by choosing a hotel near RFD after your DSM to Chicago flight. Unwind after a day of travel or just give yourself time to settle into a new destination at:
Booking at least a few weeks ahead of your flight from Des Moines International Airport to Chicago is a smart move. Along with more affordable prices, you'll have a wider selection of vehicle makes and models at RFD.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

July is the busiest month for flights from Des Moines International Airport to Chicago. To escape the crowds, visit Chicago in January.
The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your Des Moines International Airport to Chicago plane ticket then if that's your ideal forecast.
Look for cheap tickets from DSM to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Explore these hotels after locking in your flight from Des Moines International Airport to Chicago:
There are so many things to explore in this city it can be hard to work out where to start. Art Institute of Chicago, Millennium Park and Willis Tower are major attractions which should feature on every Chicago itinerary.

Explore more of the United States

Columbus is just one of the many cities in the United States waiting to be explored after you've seen Chicago. Around 451 kilometers away to the southeast, its top attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If you want to check out another side of the United States, consider Indianapolis, about 257 kilometers southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are highlights.