DSM - CHI

$81 Find Cheap Flights from Des Moines to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Des Moines to Chicago departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Des Moines to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Des Moines to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Des Moines to Chicago (DSM-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Des Moines to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Des Moines to Chicago

Sat, Oct 4 - Tue, Oct 7
Delta Logo
7:00 am - 1:03 pmDSM-MDW
6h 03m1 stop
Delta Logo
1:48 pm - 5:16 pmMDW-DSM
3h 28m1 stop
$189Delta
Find Deal
Fri, Oct 3 - Fri, Oct 10
Delta Logo
10:20 am - 4:20 pmDSM-ORD
6h 00m1 stop
Delta Logo
6:08 am - 10:26 amORD-DSM
4h 18m1 stop
$189Delta
Find Deal
Thu, Oct 2 - Thu, Oct 9
American Airlines Logo
2:21 pm - 3:58 pmDSM-ORD
1h 37mnonstop
American Airlines Logo
10:00 pm - 11:23 pmORD-DSM
1h 23mnonstop
$190American Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
American Airlines Logo
2:21 pm - 3:58 pmDSM-ORD
1h 37mnonstop
American Airlines Logo
6:55 am - 8:22 amORD-DSM
1h 27mnonstop
$191American Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
 Logo
10:41 am - 10:48 pmDSM-ORD
12h 07m1 stop
 Logo
1:26 pm - 7:57 pmORD-DSM
6h 31m1 stop
Thu, Oct 2 - Thu, Oct 9
 Logo
10:41 am - 10:48 pmDSM-ORD
12h 07m1 stop
 Logo
1:26 pm - 7:57 pmORD-DSM
6h 31m1 stop
Tue, Oct 14 - Wed, Oct 15
Southwest Logo
4:45 pm - 10:05 pmDSM-MDW
5h 20m1 stop
Southwest Logo
5:45 am - 9:30 amMDW-DSM
3h 45m1 stop
$197Southwest
Find Deal
Fri, Sep 5 - Sun, Sep 7
United Airlines Logo
3:25 pm - 4:58 pmDSM-ORD
1h 33mnonstop
United Airlines Logo
1:00 pm - 2:20 pmORD-DSM
1h 20mnonstop
$199United Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 15
Southwest Logo
4:45 pm - 10:25 pmDSM-MDW
5h 40m2 stops
Southwest Logo
5:45 am - 9:30 amMDW-DSM
3h 45m1 stop
$202Southwest
Find Deal
Thu, Sep 11 - Sat, Sep 13
United Airlines Logo
8:00 am - 9:34 amDSM-ORD
1h 34mnonstop
United Airlines Logo
1:00 pm - 2:20 pmORD-DSM
1h 20mnonstop
$245United Airlines
Find Deal
Expert advice

Expert advice for your flight from Des Moines to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Lufthansa

Economy Light is ideal for overnight trips without checked luggage, offering savings.


Economy Classic includes a checked bag up to 50 lbs, suitable for flexible travel plans.

Read more about Lufthansaby Jessica Macdonald
British Airways

BA's economy fares include a carry-on bag, avoiding surprise fees unlike budget carriers.


BA's Euro Traveller offers ergonomic seats and complimentary snacks on short flights.

United Airlines

Economy Plus provides up to six inches more legroom than standard economy seats.


Purchase Priority Boarding to ensure overhead bin space and avoid gate-checking your carry-on.

American Airlines

Consider Basic Economy for budget travel with carry-on only and no seat assignment until check-in.


Main Cabin Extra offers early boarding and complimentary drinks, ideal for quick trips.

Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan Madden

Duncan Madden

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Booking Insights

KAYAK's insights & trends for Des Moines to Chicago flights

Get data-powered insights and trends into flights from Des Moines to Chicago to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Des Moines to Chicago? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

How much is a round-trip flight from Des Moines to Chicago?

What is the cheapest Des Moines to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Des Moines to Chicago costs $228 on the route between Des Moines (DSM) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 59% cheaper than other Des Moines-Chicago routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Des Moines to Chicago?

The average price of all round-trip flights from Des Moines to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Des Moines to Chicago, you should consider leaving on a Thursday and avoid Tuesdays if you are looking for the best rates. For your return to Des Moines, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

What is the cheapest month to fly from Des Moines to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Des Moines to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Des Moines to Chicago is May, where tickets cost $224 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $279 and $276 respectively.

Can I save money by flying with a layover from Des Moines to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $207 on average.

How far in advance should I book a flight from Des Moines to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Des Moines to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Des Moines to Chicago, you should book around 5 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$81
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Des Moines to Chicago O'Hare Airport

When to book flights from Des Moines to Chicago

Are your dates flexible? Find out the best times to travel from Des Moines to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Des Moines to Chicago

  • What are the transport options from Chicago Midway International Airport?

    From MDW to downtown Chicago and other nearby cities or locations, travelers can choose between trains, shuttle buses, taxis, rideshare apps, car rental services, or free hotel shuttles to their booked hotel. From MDW to downtown Chicago the CTA train charges around $3, taxis charge around $25, Uber and Lyft charge around $30, and car rental companies charge around $36 per day for their rentals.

  • Does Chicago Midway International Airport have accessible services?

    At MDW passengers and visitors who have special needs are catered for by special facilities. The elevators, restrooms, diaper changing facilities, and telephones have amenities that are accessible for wheelchair users and people with disabilities. MDW provides numerous handicap parking spaces, and wheelchair assistance, the bus stations have special elevators for wheelchair users and there are accessible taxis that operate from the airport.

  • Which is the best airline alliance to use for flights from Des Moines to Chicago?

    Both Oneworld Alliance and Star alliance operate in DSM and MDW. Oneworld Alliance serves over 14 airlines, 1000 destinations, and over 650 lounges while Star Alliance serves over 27 airlines, over 1300 destinations, and has over 1000 lounges. Star Alliance only offers two tiers of elite status and operates in America while Oneworld offers three tiers and operates in both America and Alaska, making the latter better.

  • What cities are near Chicago Midway International Airport?

    Chicago Midway International Airport in Illinois is near cities like Burbank, Cicero, Justice, Lyons, Summit, Berwyn, and Evergreen Park.

  • What is the cheapest flight from Des Moines to Chicago?

    In the last 3 days, the lowest price for a flight from Des Moines to Chicago was $81 for a one-way ticket and $189 for a round-trip.

  • Do I need a passport to fly between Des Moines and Chicago?

    No, a passport isn't needed to fly from Des Moines to Chicago. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from Des Moines to Chicago?

    American Airlines, Delta, and Finnair offer inflight Wi-Fi service on the Des Moines to Chicago flight route.

  • Which aircraft models fly most regularly from Des Moines to Chicago?

    The Airbus A319 is the aircraft model that flies most regularly on the Des Moines to Chicago flight route.

  • Which airline alliances offer flights from Des Moines to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Des Moines and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Des Moines to Chicago?

    There are nonstop flights from Des Moines to Chicago on a daily basis.

  • Which is the best airline for flights from Des Moines to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Des Moines to Chicago are Southwest and United Airlines. With an average price for the route of $213 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $270 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Des Moines to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Des Moines to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Des Moines to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Des Moines is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Des Moines to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Des Moines with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Des Moines to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Des Moines up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Des Moines to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $241 or less one-way and $390 or less round-trip.
  • Des Moines International Airport (DSM) is a mid-sized commercial service airport in Iowa served by six airlines that offer non-stop flights to over 20 destinations worldwide. It has one main terminal and two concourses, Concourses A and C. The DSM Airport shuttle that transports visitors of DSM between the terminal and the parking lots is free.
  • On arrival at Chicago Midway International (MDW) and in need of luggage services, worry not. MDW provides free baggage carts for rent for this very purpose. You can find them at the entrances and exits of the Baggage Claim area.
  • At DSM, travelers with infants can access a private Mamava Nursing Pod sponsored by Unity Point Health to breastfeed, pump, or for diaper changing. The pod is located immediately after the TSA Security Checkpoint across the DSM Police Desk. DSM also has family rooms that can be used as an alternative to the nursing pod within the terminal.
  • Travelers at DSM are waiting for their flight and need to catch up with their work and can access the Business Center free of charge. There you can use the workstations and the free internet access provided courtesy of DSM. It’s located at Level A2 of Concourse A.
  • DSM provides both long-term and short-term parking at affordable rates for customers and visitors. Short-term parking is free for the first 20 minutes and after that, it costs around $1 for every 20 minutes to a daily maximum of around $36. On the other hand, general long-term parking charges around $2 per hour to a daily maximum of around $15 while premium long-term parking costs around $1 per 20 minutes to a daily maximum of around $25.

Prefer to fly direct from Des Moines to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Des Moines to Chicago.
Find which airlines fly direct from Des Moines Airport to Chicago, which days they fly and book direct flights.

Direct departures

Des Moines to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Des Moines

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 3 airlines serving from Des Moines to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Des Moines to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Des Moines to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4246 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

Very rough getting into denver. my kid threw up it was so rough.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Everything you need to know for your flight from Des Moines to Chicago

Information on your arrival and departure airports

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