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$109+ Cheap flights from Des Moines (DSM) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheap flight deals from Des Moines to Chicago

Cheapest flights from Des Moines to Chicago
Explore the most affordable flight options available from Des Moines to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:58 pm
DSM
-
ORD
1 stop17h 31m
Multiple Airlines
Thu 9/107:25 am
ORD
-
DSM
1 stop12h 32m
Multiple Airlines
Deal found 7/28$207
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:58 pm
DSM
-
ORD
1 stop23h 32m
Multiple Airlines
Thu 9/177:25 am
ORD
-
DSM
1 stop12h 32m
Multiple Airlines
Deal found 7/28$226
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:49 pm
DSM
-
ORD
Nonstop1h 48m
American Airlines
Mon 8/248:26 am
ORD
-
DSM
Nonstop1h 30m
American Airlines
Deal found 7/28$236
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:40 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 8/248:50 pm
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 7/30$237
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
DSM
-
ORD
Nonstop1h 36m
United Airlines
Mon 8/2412:50 pm
ORD
-
DSM
Nonstop1h 26m
United Airlines
Deal found 7/30$237
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:55 am
DSM
-
ORD
Nonstop1h 50m
American Airlines
Fri 9/1112:27 pm
ORD
-
DSM
Nonstop1h 32m
American Airlines
Deal found 7/29$242
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 am
DSM
-
MDW
Nonstop1h 15m
Southwest
Sat 9/192:05 pm
MDW
-
DSM
1 stop6h 45m
Southwest
Deal found 7/29$247
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:30 am
DSM
-
MDW
Nonstop1h 15m
Southwest
Sat 9/510:10 am
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 8/1$249
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:52 pm
DSM
-
ORD
Nonstop1h 38m
American Airlines
Thu 1/711:55 am
ORD
-
DSM
Nonstop1h 35m
American Airlines
Deal found 7/29$249
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:15 am
DSM
-
MDW
2 stops9h 45m
Southwest
Thu 8/2710:05 am
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 7/28$252
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:25 pm
DSM
-
MDW
1 stop4h 32m
Delta
Sat 9/199:59 am
MDW
-
DSM
1 stop4h 07m
Delta
Deal found 7/29$257
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:10 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Tue 9/228:35 pm
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 8/1$261

Find flight deals from Des Moines to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Des Moines (DSM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$273

Good round-trip deal

$378 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
Search Deals
From Des Moines to Chicago (CHI)
Search Deals
One-way flight from Des Moines to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Des Moines to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Des Moines to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Des Moines to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 1, 2026.
Use the filters below to find and compare flights from Des Moines to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 9/5

5:30 am-6:45 am

Nonstop1h 15m

Chicago Midway

Sun 9/6

11:00 am-12:20 pm

Nonstop1h 20m

$237

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 8/24

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Wed 8/26

8:35 pm-9:55 pm

Nonstop1h 20m

$237

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 9/10

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Thu 9/17

8:50 pm-10:15 pm

Nonstop1h 25m

$237

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 8/20

5:40 am-7:00 am

Nonstop1h 20m

Chicago Midway

Mon 8/24

8:50 pm-10:10 pm

Nonstop1h 20m

$237

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 8/20

3:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Sat 8/22

10:10 am-11:30 am

Nonstop1h 20m

$237

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 9/12

5:30 am-6:45 am

Nonstop1h 15m

Chicago Midway

Sat 9/19

2:05 pm-8:50 pm

1 stop6h 45m

$247

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Mon 8/24

5:56 pm-9:47 pm

1 stop3h 51m

Chicago O'Hare Intl

Mon 8/31

1:59 pm-8:39 pm

1 stop6h 40m

$257

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 9/15

6:10 am-7:30 am

Nonstop1h 20m

Chicago Midway

Tue 9/22

8:35 pm-10:00 pm

Nonstop1h 25m

$261

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 9/14

3:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Mon 9/21

10:05 am-11:25 am

Nonstop1h 20m

$261

Des MoinesChicago

DSM - RFD

DSMRFD

Des Moines

Thu 8/20

9:28 am-3:09 pm

1 stop5h 41m

Chicago Greater Rockford

Sun 8/23

9:35 pm-7:48 pm

1 stop22h 13m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 56 resultsSorted by cheapest first
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Compare providers for flights from Des Moines to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Des Moines to Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Des Moines-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Des Moines-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Des Moines-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Des Moines-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Des Moines-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Des Moines to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Des Moines with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Des Moines to Chicago?

Currently, October is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $237). Flying from Des Moines to Chicago in July is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DSM to CHI?

Find hourly flight availability from Des Moines to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 42% on flights from Des Moines to Chicago by exploring options for tickets in the morning.

Weekly flight availability from Des Moines to Chicago

Explore weekly flight availability from Des Moines to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 1, 2026.

The most flights from DSM to CHI are scheduled on a Friday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Des Moines to Chicago?

Airfare is below average for this route at the moment.
Des Moines to Chicago flights typically cost between $224 and $359 in September.
The cheapest round-trip price found within the last 5 days was $207 on Multiple Airlines (Sep 6-Sep 10).

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

Booking 18 days in advance of your planned departure date is, on average, the best time to get cheap flights from Des Moines to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Des Moines to Chicago. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Des Moines to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Des Moines to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Des Moines to Chicago trip
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Harriet Baskas

Harriet Baskas

Expert on United 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.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 1, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Des Moines to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,062 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Des Moines to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Des Moines to Chicago?

    Most people fly from Des Moines (DSM) if they book a flight from Des Moines to Chicago. On average, Des Moines has 23 outbound flights to Chicago per day from 2 airlines. Des Moines is conveniently located just 3.6 mi from Des Moines’s city center.

  • How long is the flight from Des Moines to Chicago?

    Airlines like Southwest, Delta, and Allegiant Air fly from Des Moines to Chicago in about 1h 15m. The time it takes to get you to your destination can typically vary by up to 4h 26m. Airlines will cover a distance of 305 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Des Moines to Chicago round-trip?

    Our cheapest airline available from Des Moines to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $148 on this airline. An additional option worth looking into is United Airlines, starting at $189. American Airlines is currently priced 51% below the average price you’ll pay for this route.

  • What are the most popular routes from Des Moines to Chicago?

    When deciding which route to take from Des Moines to Chicago consider Des Moines - Chicago O'Hare Intl, Des Moines - Chicago Midway or Des Moines - Chicago Greater Rockford as they are the most popular.

  • What are the most reliable airlines from Des Moines to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Des Moines to Chicago on time: Japan Airlines (86%), Copa Airlines (81%), Alaska Airlines (79%).

  • What are the cheapest flights from Des Moines to Chicago?

    Looking for the cheapest flight from Des Moines to Chicago? While on average our users pay $1,422, our data indicates the cheapest price to be $154. The most popular route (Des Moines - Chicago O'Hare Intl), is priced around $237.

  • Can I find deals for flights from Des Moines to Chicago that include hotel bookings?

    Yes. In addition to deals on Des Moines to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Des Moines to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Des Moines to Chicago.

  • Can I find deals for business class flights from Des Moines to Chicago?

    Yes. Cheapflights offers flight deals from Des Moines to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, October is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $237). Flying from Des Moines to Chicago in July is currently the most expensive (average of $419). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 2 airlines flying from Des Moines to Chicago

Discover the top 2 airlines that operate flights from Des Moines to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$285FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$324FlexibilityNo cancel feeOn-time69%

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