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$90+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Apr 15 — Apr 221
Wed 4/15
Wed 4/22
1 adult, Economy
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Cheapflights Tip: The best prices from Des Moines to Chicago are usually found in September or October, booked 41 days in advance, depart on a Thursday or Friday and return on a Saturday

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 March 16, 2026.

This Southwest deal was found by Cheapflights users on 3/12. 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 4/215:30 am
DSM
-
MDW
Nonstop1h 25m
Southwest
Tue 4/2110:00 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 3/12$253
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Tue 5/195:00 am
DSM
-
ORD
Nonstop1h 38m
United Airlines
Wed 5/207:50 pm
ORD
-
DSM
Nonstop1h 33m
United Airlines
Deal found 3/11$253
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Wed 5/272:16 pm
DSM
-
ORD
1 stop6h 21m
Multiple Airlines
Fri 5/298:05 am
ORD
-
DSM
1 stop15h 19m
Multiple Airlines
Deal found 3/13$254
This Southwest deal was found by Cheapflights users on 3/12. 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 4/283:15 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Thu 4/3010:20 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 3/12$255
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 4/31:10 pm
DSM
-
ORD
Nonstop1h 36m
United Airlines
Tue 4/78:00 pm
ORD
-
DSM
Nonstop1h 32m
United Airlines
Deal found 3/12$255
This Southwest deal was found by Cheapflights users on 3/11. 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 4/255:35 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Sat 5/210:05 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 3/11$257
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Thu 3/268:00 am
DSM
-
ORD
Nonstop1h 36m
United Airlines
Sat 3/288:10 pm
ORD
-
DSM
Nonstop1h 30m
United Airlines
Deal found 3/12$257
This American Airlines deal was found by Cheapflights users on 3/12. 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.
Sun 4/262:16 pm
DSM
-
ORD
Nonstop1h 43m
American Airlines
Sun 5/312:15 pm
ORD
-
DSM
Nonstop1h 31m
American Airlines
Deal found 3/12$258
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Sat 4/256:00 am
DSM
-
ORD
Nonstop1h 41m
American Airlines
Sat 5/26:53 am
ORD
-
DSM
Nonstop1h 33m
American Airlines
Deal found 3/11$259
This Southwest deal was found by Cheapflights users on 3/11. 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 4/234:20 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Sun 4/269:55 pm
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 3/11$264
This Southwest deal was found by Cheapflights users on 3/12. 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 4/286:55 am
DSM
-
MDW
1 stop5h 00m
Southwest
Fri 5/110:20 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 3/12$265
This Southwest deal was found by Cheapflights users on 3/12. 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 4/255:35 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 4/273:30 pm
MDW
-
DSM
1 stop6h 25m
Southwest
Deal found 3/12$267

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 March 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Southwest)

One-way from

$90
(Frontier)

Popular in

March

Cheapest in

September

Average price

$289

Good round-trip deal

$387 or less

Good one-way deal

$193 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. 5% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 16, 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 4/25

5:35 am-6:55 am

Nonstop1h 20m

Chicago Midway

Sat 5/2

10:05 am-11:30 am

Nonstop1h 25m

$257

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 4/17

8:04 am-9:36 am

Nonstop1h 32m

Chicago O'Hare Intl

Sun 4/19

9:40 pm-11:17 pm

Nonstop1h 37m

$257

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Fri 3/27

4:20 pm-5:40 pm

Nonstop1h 20m

Chicago Midway

Sun 3/29

10:10 pm-11:35 pm

Nonstop1h 25m

$257

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Mon 4/27

4:20 pm-5:40 pm

Nonstop1h 20m

Chicago Midway

Mon 5/4

3:30 pm-9:55 pm

1 stop6h 25m

$267

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 4/14

4:23 pm-9:38 pm

1 stop5h 15m

Chicago O'Hare Intl

Fri 4/17

1:36 pm-8:49 pm

1 stop7h 13m

$275

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 4/1

10:28 am-4:43 pm

1 stop6h 15m

Chicago O'Hare Intl

Sat 4/4

9:50 am-4:54 pm

1 stop7h 04m

$275

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sat 4/25

6:40 am-2:20 pm

1 stop7h 40m

Chicago O'Hare Intl

Sat 5/2

3:05 pm-8:55 pm

1 stop5h 50m

$277

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 4/30

5:25 am-6:45 am

Nonstop1h 20m

Chicago Midway

Thu 5/7

10:20 am-11:45 am

Nonstop1h 25m

$291

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 4/4

5:20 am-6:40 am

Nonstop1h 20m

Chicago Midway

Sat 4/4

10:05 am-11:30 am

Nonstop1h 25m

$291

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Mon 4/27

4:23 pm-9:38 pm

1 stop5h 15m

Chicago O'Hare Intl

Mon 5/4

6:25 am-10:16 am

1 stop3h 51m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 58 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 March.
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

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

Use this chart to determine the optimal time to book a round-trip flight from Des Moines to Chicago. Price data was last updated on March 13, 2026.

Booking 41 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 month to book a flight from Des Moines to Chicago?

Currently, February is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $140). Flying from Des Moines to Chicago in January is currently the most expensive (average of $189). 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 March 16, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 31% on flights from Des Moines to Chicago by exploring options for tickets in the morning.

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 March 12, 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.

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 March 16, 2026.

The most flights from DSM to CHI are scheduled on a Friday (48 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (33 on average).

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

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 March 16, 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
4,318 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Southwest
8.0
Very good
4,318 reviews
Southwest
8.0
Very good
4,318 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
United Airlines
7.4
Good
9,428 reviews
Southwest
8.0
Very good
4,318 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
American Airlines
7.1
Good
11,467 reviews
Southwest
8.0
Very good
4,318 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..

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 40 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, United Airlines, and Delta fly from Des Moines to Chicago in about 1h 20m. The time it takes to get you to your destination can typically vary by up to 3h 55m. 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 41% 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 (74%), Emirates (72%), Qatar Airways (71%).

  • 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 $921, our data indicates the cheapest price to be $138. 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, February is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $140). Flying from Des Moines to Chicago in January is currently the most expensive (average of $189). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 March 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$234FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$256FlexibilityNo cancel feeOn-time69%

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