Cheap Flights from Des Moines to Chicago from $267

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Flight deals from Des Moines Airport 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 $303. Find the lowest prices on one-way and return tickets right here.

Chicago.$267 per passenger.Departing Tue, 5 May, returning Tue, 12 May.Return flight with United.Outbound direct flight with United departs from Des Moines on Tue, 5 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 12 May, arriving in Des Moines.Price includes taxes and charges.From $267, select.

Chicago.$301 per passenger.Departing Tue, 28 Apr, returning Sat, 2 May.Return flight with United.Outbound direct flight with United departs from Des Moines on Tue, 28 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 2 May, arriving in Des Moines.Price includes taxes and charges.From $301, select.

Chicago.$303 per passenger.Departing Tue, 14 Apr, returning Thu, 16 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Tue, 14 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 16 Apr, arriving in Des Moines.Price includes taxes and charges.From $303, select.

Chicago.$318 per passenger.Departing Wed, 25 Mar, returning Fri, 27 Mar.Return flight with United.Outbound direct flight with United departs from Des Moines on Wed, 25 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 27 Mar, arriving in Des Moines.Price includes taxes and charges.From $318, select.

Chicago.$351 per passenger.Departing Mon, 30 Mar, returning Fri, 10 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Mon, 30 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 10 Apr, arriving in Des Moines.Price includes taxes and charges.From $351, select.

Chicago.$365 per passenger.Departing Mon, 1 Jun, returning Sun, 7 Jun.Return flight with United.Outbound direct flight with United departs from Des Moines on Mon, 1 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 7 Jun, arriving in Des Moines.Price includes taxes and charges.From $365, select.

Chicago.$365 per passenger.Departing Thu, 16 Jul, returning Sun, 19 Jul.Return flight with United.Outbound direct flight with United departs from Des Moines on Thu, 16 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 19 Jul, arriving in Des Moines.Price includes taxes and charges.From $365, select.

Chicago.$370 per passenger.Departing Tue, 3 Nov, returning Fri, 13 Nov.Return flight with United.Outbound direct flight with United departs from Des Moines on Tue, 3 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 13 Nov, arriving in Des Moines.Price includes taxes and charges.From $370, select.

Chicago.$402 per passenger.Departing Thu, 13 Aug, returning Sun, 16 Aug.Return flight with United.Outbound direct flight with United departs from Des Moines on Thu, 13 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 16 Aug, arriving in Des Moines.Price includes taxes and charges.From $402, select.

Chicago.$402 per passenger.Departing Fri, 15 May, returning Sat, 22 Aug.Return flight with United.Outbound direct flight with United departs from Des Moines on Fri, 15 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 22 Aug, arriving in Des Moines.Price includes taxes and charges.From $402, select.

Chicago.$436 per passenger.Departing Sun, 30 Aug, returning Tue, 8 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Des Moines on Sun, 30 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 8 Sep, arriving in Des Moines.Price includes taxes and charges.From $436, select.

Chicago.$436 per passenger.Departing Sat, 19 Dec, returning Tue, 19 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Des Moines on Sat, 19 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 19 Jan, arriving in Des Moines.Price includes taxes and charges.From $436, select.

Chicago.$452 per passenger.Departing Thu, 10 Sep, returning Thu, 10 Sep.Return flight with United.Outbound direct flight with United departs from Des Moines on Thu, 10 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 10 Sep, arriving in Des Moines.Price includes taxes and charges.From $452, select.

Chicago.$472 per passenger.Departing Mon, 21 Dec, returning Sun, 3 Jan.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Des Moines on Mon, 21 Dec, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departs from Chicago O'Hare International on Sun, 3 Jan, arriving in Des Moines.Price includes taxes and charges.From $472, select.

Chicago.$500 per passenger.Departing Sun, 30 Aug, returning Tue, 8 Sep.Return flight with United.Outbound direct flight with United departs from Des Moines on Sun, 30 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 8 Sep, arriving in Des Moines.Price includes taxes and charges.From $500, 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 May.

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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	$267
Cheapest month to fly	May
Average flight time	1 hr, 29 mins
Most popular airline	American Airlines
Average flights per week	592

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 $267. 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 29 minutes is the average flight time from Des Moines to Chicago.

Which airlines fly direct from Des Moines to Chicago?

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

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

As of March 2026, there are 592 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 May.

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 $267.

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 Tuesday, 5 May 2026.

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

Yes – the average flight time is 1 hour and 29 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 March, the average temperature is usually around 3°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, United offers the cheapest flight tickets to Chicago.

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

Jump on a direct flight from Des Moines International Airport to Chicago and you'll be travelling for around 1 hour 25 minutes.
Des Moines (the location of Des Moines International Airport) and Chicago follow the same timezone — UTC-5.
The busiest route is from Des Moines International Airport (DSM) to O'Hare International Airport (ORD). Choose from 58 weekly services between these two airports. If you want to head off as soon as possible, the earliest flight from DSM to ORD is the 05:00 American Airlines option. If you prefer travelling later, the final departure is at 18:50 with United Airlines.
For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to board your DSM to Chicago flight.
Taking off during a peak time like school or public holidays? Expect longer queues at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.
Direct Des Moines International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) will be your arrival point.
Book your favourite seat with United Airlines. This airline operates direct flights from Des Moines International Airport to Chicago.
The journey from central Des Moines to DSM takes around 45 minutes on public transport. If you drive, ride-share or take a cab, you'll cover the 6 kilometres in 15 minutes or so, depending on traffic.
Planning to catch an early flight from Des Moines International Airport to Chicago? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by choosing one of these hotels close to DSM:
Des Moines International Airport gets top marks for on-time performance. 80.45% of flights that depart DSM land 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 seen for a one-way Des Moines International Airport to Chicago flight is $167. The cheapest price for a return flight is $267. Keep in mind fares may change due to demand at the time of booking.
To score cheap flights from DSM to Chicago, reserve your journey one month before your departure date.
May is the best month for scoring a fantastic deal on Des Moines International Airport to Chicago tickets. If you're looking to travel during a different time of year, the 'Whole month' tool will give you the lowest prices across every month.
You don't need to check every day to see if fares have dropped when you set up a Price Alert. We'll notify you when there's an even bigger deal on 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 preferred duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes around 35 minutes to get to the centre driving.
Travelling to the centre by public transport will take you around 55 minutes.
If you're coming in on a late flight from Des Moines International Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and relaxing not long after at one of these accommodation options near ORD:
Travel at your own pace with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and venture far and wide through Chicago and beyond.
Lock in the best possible rate by reserving your ride from O'Hare International Airport around four weeks in advance of your flight from DSM to Chicago.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is roughly 19 kilometres from the centre of Chicago. Once you've disembarked your flight from Des Moines International Airport to Chicago, it'll take you around 20 minutes to get to the heart of the city in a cab or ride-share.
You can expect the trip to take about 45 minutes on public transport.
Hang up the 'Do not disturb' sign and unwind at a hotel close to MDW. Here are a few options where you can settle in after your DSM to Chicago flight:
The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and make a speedy getaway.
Avoid last-minute price surges. Reserving your ride four weeks ahead of your arrival at MDW will save you money.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Hop off your flight from Des Moines International Airport to Chicago and head for your hotel or jump right into exploring. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach driving.
If you're using public transport, the journey time is around 4 hours 15 minutes.
If you don't want to make the journey into the centre, choose a hotel close to RFD. Get settled at one of these stays after your DSM to Chicago flight:
Whether you're searching for a mini for a solo adventure or a roomy SUV to fit the family, you'll find the perfect Chicago Rockford International Airport rental car for you. Browse the types of wheels available here from providers such as Budget, Alamo and National.
Booking at least a few weeks in advance of your flight from Des Moines International Airport to Chicago is a good move. As well as better prices, you might find it easier to get the make and model you prefer at RFD.
The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

Visit Chicago in peak season if you want a lively atmosphere, but remember that hotel prices are usually higher. Alternatively, book flights from Des Moines International Airport to Chicago in the low season when prices are cheaper and it's quieter.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your Des Moines International Airport to Chicago flight ticket then if that's your ideal forecast.
Look for cheap tickets from DSM to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best places to stay in Chicago right here. Check out these hotels after locking in your flight from Des Moines International Airport to Chicago:
There are so many things to see and do in this city it can be hard to work out where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top sights which should be on any well-planned Chicago itinerary.

Explore more of United States

You've visited Chicago, now it's time to discover other parts of United States. Travel around 451 kilometres south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.
Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience the best of this destination with a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.