DSM - CHI

$86 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 11/17. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$189
Overall average: $251
United Airlines
Fri 12/5Mon 12/8
DSM - ORD • Non-stop
Cheapest one-way
$86
Typical prices: $201-$271
Frontier
Mon 11/17
DSM - ORD • 1 stop
Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom for comfort.
American's Basic Economy is budget-friendly with carry-on only.
Expert advice
Expert advice
Expert advice
Expert advice
Video guide: How to find cheap flights to Chicago
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Top airlines
United Airlines
Cheapest • from $189 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DSM-ORD
Cheapest • 27% average savings
DSM-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 17% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
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Expert advice
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

Fri, Dec 5 - Mon, Dec 8
United Airlines Logo
11:35 am - 1:06 pmDSM-ORD
1h 31mnonstop
United Airlines Logo
1:00 pm - 2:20 pmORD-DSM
1h 20mnonstop
$189United Airlines
Find Deal
Fri, Dec 19 - Fri, Dec 26
American Airlines Logo
6:35 pm - 8:26 pmDSM-ORD
1h 51mnonstop
American Airlines Logo
6:40 am - 8:15 amORD-DSM
1h 35mnonstop
$190American Airlines
Find Deal
Tue, Dec 2 - Sat, Dec 20
Delta Logo
4:59 pm - 9:40 pmDSM-ORD
4h 41m1 stop
Delta Logo
6:35 am - 11:28 amORD-DSM
4h 53m1 stop
$202Delta
Find Deal
Mon, Nov 24 - Sun, Nov 30
United Airlines Logo
11:26 am - 12:57 pmDSM-ORD
1h 31mnonstop
United Airlines Logo
10:40 am - 12:14 pmORD-DSM
1h 34mnonstop
$204United Airlines
Find Deal
Sat, Dec 13 - Mon, Dec 15
Southwest Logo
6:25 am - 3:20 pmDSM-MDW
8h 55m1 stop
Southwest Logo
6:20 am - 11:25 amMDW-DSM
5h 05m1 stop
$207Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Delta Logo
6:17 am - 12:34 pmDSM-MDW
6h 17m1 stop
Delta Logo
9:59 am - 2:19 pmMDW-DSM
4h 20m1 stop
$209Delta
Find Deal
Wed, Dec 3 - Fri, Dec 5
Southwest Logo
4:15 pm - 10:35 pmDSM-MDW
6h 20m2 stops
Southwest Logo
6:20 am - 11:25 amMDW-DSM
5h 05m1 stop
$214Southwest
Find Deal
Fri, Dec 5 - Fri, Dec 12
Frontier Logo
7:58 pm - 1:59 pmDSM-MDW
18h 01m2 stops
Frontier Logo
12:18 pm - 7:03 pmMDW-DSM
6h 45m1 stop
$226Frontier
Find Deal
Fri, Mar 6 - Sat, Mar 7
American Airlines Logo
7:46 pm - 9:25 pmDSM-ORD
1h 39mnonstop
American Airlines Logo
8:00 am - 9:30 amORD-DSM
1h 30mnonstop
$234American Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 11
Frontier Logo
8:25 pm - 10:49 amDSM-ORD
14h 24m2 stops
Frontier Logo
7:51 pm - 7:30 pmORD-DSM
23h 39m1 stop
$253Frontier
Find Deal
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.

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 $219 on the route between Des Moines (DSM) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 27% 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 September, where tickets cost $208 (return) on average. On the other hand, the most expensive months are October and July, where the average cost of round-trip tickets is $284 and $279 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.

No, with an average price for the route of $224, prices are generally cheapest when you fly direct.

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 2 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

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

Good to know

Low seasonFebruary
Cheapest flight$86
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 1% 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 $86 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, Air France, Finnair, and Aeromexico 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 oneworld 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 $218 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 $278 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 $230 or less one-way and $423 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 4241 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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.

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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

Information on your arrival and departure airports