DSM - CHI

$104 Find Cheap Flights from Des Moines to Chicago - Compare and Save

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 8/11. 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

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Everything you should know

Cheapest round-trip
$207
Typical prices: $243-$409
American Airlines
Fri 8/7Mon 8/10
DSM - ORD • Non-stop
Cheapest non-stop
$206
Typical prices: $194-$409
American Airlines
Sat 8/22Sat 8/29
DSM - ORD • Non-stop
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 33m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 7% average savings
Most popular
Insights
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Top layover airports
Cheapest • Avg $169 (round-trip)
Shortest trip • 3h 19m (one-way)
Insights
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
Good to know
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Flight Deals
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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

Fri, Aug 7 - Mon, Aug 10
American Airlines Logo
6:55 am - 8:45 am
DSM
-
ORD
1h 50mnonstop
American Airlines Logo
10:45 pm - 12:20 am
ORD
-
DSM
1h 35mnonstop
$207American Airlines
Mon, Aug 24 - Thu, Aug 27
American Airlines Logo
7:49 pm - 9:37 pm
DSM
-
ORD
1h 48mnonstop
American Airlines Logo
10:45 pm - 12:20 am
ORD
-
DSM
1h 35mnonstop
$209American Airlines
Thu, Aug 27 - Tue, Sep 1
Southwest Logo
3:50 pm - 5:10 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
8:35 pm - 9:55 pm
MDW
-
DSM
1h 20mnonstop
$210Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
2:40 pm - 4:00 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
10:30 am - 11:50 am
MDW
-
DSM
1h 20mnonstop
$218Southwest
Thu, Aug 27 - Tue, Sep 1
Southwest Logo
3:50 pm - 5:10 pm
DSM
-
MDW
1h 20mnonstop
Southwest Logo
2:15 pm - 9:00 pm
MDW
-
DSM
6h 45m
1 stop
$220Southwest
Wed, Aug 12 - Thu, Aug 13
Frontier Logo
2:19 pm - 8:52 pm
DSM
-
ORD
6h 33m
1 stop
Frontier Logo
9:57 pm - 1:34 pm
ORD
-
DSM
15h 37m
1 stop
$240Frontier
Wed, Aug 12 - Thu, Aug 13
Frontier Logo
2:19 pm - 8:52 pm
DSM
-
ORD
6h 33m
1 stop
Frontier Logo
9:57 pm - 1:34 pm
ORD
-
DSM
15h 37m
1 stop
$242Frontier
Fri, Aug 7 - Mon, Aug 10
Delta Logo
2:45 pm - 7:30 pm
DSM
-
ORD
4h 45m
1 stop
Delta Logo
6:00 am - 10:18 am
ORD
-
DSM
4h 18m
1 stop
$259Delta
Wed, Sep 30 - Sun, Oct 4
Allegiant Air Logo
2:42 pm - 8:13 pm
DSM
-
RFD
29h 31m
1 stop
Allegiant Air Logo
10:08 am - 8:53 pm
RFD
-
DSM
10h 45m
1 stop
$296Allegiant Air
Fri, Aug 7 - Sun, Aug 9
Allegiant Air Logo
8:00 am - 8:34 pm
DSM
-
RFD
12h 34m
1 stop
Allegiant Air Logo
11:37 am - 5:17 pm
RFD
-
DSM
29h 40m
1 stop
$361Allegiant 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.

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 August.

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 $273 on the route between Des Moines (DSM) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 7% 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 Mondays if you are looking for the best rates. For your return to Des Moines, you’ll find the best rates on Saturdays 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 February, where tickets cost $126 (return) on average. On the other hand, the most expensive months are January and October, where the average cost of round-trip tickets is $189 and $189 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 $325 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 3 weeks before departure, which saves you about 46% 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

 
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 seasonApril
Cheapest flight$104
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 24% 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 5 days, the lowest price for a flight from Des Moines to Chicago was $104 for a one-way ticket and $207 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 JetBlue 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 $283 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $299 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 $236 or less one-way and $406 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

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

Information on your arrival and departure airports