DSM - CHI

$56 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 5/16. 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
$151
Overall average: $199
American Airlines
Wed 4/1Sat 4/4
DSM - ORD • Non-stop
Cheapest one-way
$56
Southwest
Sat 5/16
DSM - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
American Airlines
Cheapest • from $151 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DSM
-
ORD
Cheapest • 8% average savings
DSM
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 17% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Wed, Apr 1 - Sat, Apr 4
American Airlines Logo
7:44 pm - 9:19 pm
DSM
-
ORD
1h 35mnonstop
American Airlines Logo
10:26 pm - 11:48 pm
ORD
-
DSM
1h 22mnonstop
$151American Airlines
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
7:44 pm - 9:17 pm
DSM
-
ORD
1h 33mnonstop
American Airlines Logo
7:35 am - 8:59 am
ORD
-
DSM
1h 24mnonstop
$152American Airlines
Tue, Mar 10 - Tue, Mar 17
United Airlines Logo
2:04 pm - 3:41 pm
DSM
-
ORD
1h 37mnonstop
United Airlines Logo
11:50 am - 1:23 pm
ORD
-
DSM
1h 33mnonstop
$157United Airlines
Wed, Apr 1 - Tue, Apr 7
Southwest Logo
3:40 pm - 4:55 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
8:50 pm - 10:10 pm
MDW
-
DSM
1h 20mnonstop
$157Southwest
Wed, Apr 1 - Tue, Apr 7
Southwest Logo
3:40 pm - 4:55 pm
DSM
-
MDW
1h 15mnonstop
Southwest Logo
6:30 am - 2:05 pm
MDW
-
DSM
7h 35m
1 stop
$167Southwest
Wed, Apr 1 - Sat, Apr 4
Delta Logo
6:55 am - 11:35 am
DSM
-
ORD
4h 40m
1 stop
Delta Logo
12:15 pm - 3:42 pm
ORD
-
DSM
3h 27m
1 stop
$167Delta
Sat, Feb 28 - Mon, Mar 2
United Airlines Logo
6:55 pm - 8:31 pm
DSM
-
ORD
1h 36mnonstop
United Airlines Logo
8:10 pm - 9:41 pm
ORD
-
DSM
1h 31mnonstop
$170United Airlines
Sat, Mar 7 - Mon, Mar 9
Delta Logo
6:19 am - 12:46 pm
DSM
-
MDW
6h 27m
1 stop
Delta Logo
9:30 am - 3:42 pm
MDW
-
DSM
6h 12m
1 stop
$174Delta
Fri, Jun 12 - Sun, Jun 14
Allegiant Air Logo
7:00 am - 8:20 pm
DSM
-
RFD
13h 20m
1 stop
Allegiant Air Logo
11:27 am - 5:54 pm
RFD
-
DSM
30h 27m
1 stop
$487Allegiant Air
Thu, Feb 26 - Thu, Mar 12
Allegiant Air Logo
8:30 am - 5:02 pm
DSM
-
RFD
8h 32m
1 stop
Allegiant Air Logo
10:37 am - 8:14 pm
RFD
-
DSM
9h 37m
1 stop
$490Allegiant Air
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Des Moines to Chicago departing in April.

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 absolute cheapest return flight from Des Moines to Chicago costs $255 on the route between Des Moines (DSM) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Des Moines (DSM) and Chicago Midway Airport (MDW) were, on average, 8% cheaper than other Des Moines-Chicago routes. The most popular route is between Des Moines (DSM) and Chicago O'Hare Intl Airport (ORD).

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 July and August, where the average cost of round-trip tickets is $279 and $273 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 $265, 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 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Expert advice

Expert advice for your flight from Des Moines to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

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.

Duncan Madden

Duncan Madden

Expert on British Airways

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Good to know

Low seasonFebruary
Cheapest flight$56
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 12% increase in price.
Flight from Des Moines to Chicago Midway 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 $56 for a one-way ticket and $151 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, JetBlue, 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 Embraer 175 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 $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 $277 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 $201 or less one-way and $401 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, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Chicago to Des Moines

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

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 4280 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

10.0 ExcellentAnonymous, Feb 2026
STL - DAL
Read more Southwest reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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.

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

Information on your arrival and departure airports