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$74+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Des Moines to Chicago are usually found in May or September, booked 82 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 July 3, 2025.

Round-trip from

$189
(Southwest)

One-way from

$74
(Mytrip)

Popular in

August

Cheapest in

May

Average price

$289

Good round-trip deal

$377 or less

Good one-way deal

$232 or less
From Des Moines to Chicago (CHI)
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One-way flight from Des Moines to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Des Moines to Chicago (CHI).
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Price to beat on a one-way flight from Des Moines to Chicago (CHI).
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Find 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 8/163:45 pmDSM - MDW
1 stop5h 15mSouthwest
Wed 8/205:40 pmMDW - DSM
1 stop4h 40mSouthwest
Deal found 7/2$189
This Southwest deal was found by Cheapflights users on 7/2. 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 8/166:10 amDSM - ORD
1 stop6h 55mSouthwest
Wed 8/207:00 amORD - DSM
1 stop7h 40mSouthwest
Deal found 7/2$189
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/65:00 amDSM - ORD
Nonstop1h 30mAmerican Airlines
Sat 8/97:00 amORD - DSM
Nonstop1h 31mAmerican Airlines
Deal found 7/1$190
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/177:15 pmDSM - ORD
2 stops23h 52mMultiple Airlines
Sun 8/248:12 pmORD - DSM
2 stops24h 29mMultiple Airlines
Deal found 7/3$193
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/136:00 amDSM - MDW
1 stop6h 28mDelta
Mon 8/189:15 amMDW - DSM
1 stop4h 54mDelta
Deal found 7/2$209
This Delta deal was found by Cheapflights users on 7/3. 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.
Sun 8/176:00 amDSM - ORD
1 stop4h 20mDelta
Sun 8/246:10 amORD - DSM
1 stop4h 08mDelta
Deal found 7/3$209
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Thu 7/246:50 pmDSM - ORD
Nonstop1h 35mUnited Airlines
Mon 7/289:29 pmORD - DSM
Nonstop1h 31mUnited Airlines
Deal found 6/30$251
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:54 pmDSM - RFD
1 stop11h 48mAllegiant Air
Mon 8/48:04 pmRFD - DSM
1 stop17h 27mAllegiant Air
Deal found 7/1$252
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:54 pmDSM - MDW
2 stops18h 02mAllegiant Air
Mon 8/42:46 pmMDW - DSM
2 stops22h 45mAllegiant Air
Deal found 7/1$333
This Orbitz deal was found by Cheapflights users on 7/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/77:33 pmDSM - MDW
2 stops15h 07mFrontier
Fri 7/1112:35 pmMDW - DSM
1 stop6h 13mFrontier
Deal found 7/2$341
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/106:32 pmDSM - RFD
2 stops24h 47mMultiple Airlines
Sun 7/139:21 amRFD - DSM
3 stops27h 25mMultiple Airlines
Deal found 7/2$446

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 July 3, 2025.
Use the filters below to find and compare flights from Des Moines to Chicago that are best for you.

Fly from

Des Moines

Fly to

Chicago

Route

Depart

Return

Price

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/16

3:45 pm-9:00 pm

1 stop5h 15m

Chicago Midway

Wed 8/20

5:40 pm-10:20 pm

1 stop4h 40m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sat 8/16

6:10 am-1:05 pm

1 stop6h 55m

Chicago O'Hare Intl

Wed 8/20

7:00 am-2:40 pm

1 stop7h 40m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 8/6

5:00 am-6:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Sat 8/9

7:00 am-8:31 am

Nonstop1h 31m

$190

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sun 8/17

7:15 pm-7:07 pm

2 stops23h 52m

Chicago O'Hare Intl

Sun 8/24

8:12 pm-8:41 pm

2 stops24h 29m

$193

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 8/13

6:00 am-12:28 pm

1 stop6h 28m

Chicago Midway

Mon 8/18

9:15 am-2:09 pm

1 stop4h 54m

$209

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sun 8/17

6:00 am-10:20 am

1 stop4h 20m

Chicago O'Hare Intl

Sun 8/24

6:10 am-10:18 am

1 stop4h 08m

$209

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 8/15

6:50 pm-8:25 pm

Nonstop1h 35m

Chicago O'Hare Intl

Sun 8/17

9:29 pm-11:00 pm

Nonstop1h 31m

$249

Des MoinesChicago

DSM - RFD

DSMRFD

Des Moines

Thu 7/31

7:54 pm-7:42 am

1 stop11h 48m

Chicago Greater Rockford

Mon 8/4

8:04 pm-1:31 pm

1 stop17h 27m

$252

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 7/31

7:54 pm-1:56 pm

2 stops18h 02m

Chicago Midway

Mon 8/4

2:46 pm-1:31 pm

2 stops22h 45m

$333

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Mon 8/4

1:59 pm-9:30 pm

1 stop7h 31m

$74

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 20 results
1
2

The best insider tips for Des Moines to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Des Moines to Chicago trip
Airlines
British Airways

BA's Executive Club offers free seat selection for oneworld Sapphire or Emerald members.


BA's Avios can be transferred between IAG airlines, offering flexible redemption options.

Read more about British Airwaysby Gabriel Leigh
United Airlines

United's Economy Plus offers extra legroom and priority boarding for a more comfortable short flight.


Prepay checked bags 24 hours before to save on fees; premium cabins include free checked bags.

Read more about United Airlinesby Harriet Baskas
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel Leigh

Gabriel Leigh

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 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

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 June 27, 2025.

Booking 81 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, August is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $245). Flying from Des Moines to Chicago in March is currently the most expensive (average of $321). 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 July 3, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 54% 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 July 3, 2025.

The most flights from DSM to CHI are scheduled on a Thursday (46 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

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

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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    Our cheapest airline available from Des Moines to Chicago is Southwest. Our recent data shows that you can find tickets from as low as $189 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $190 and $209 round-trip. Southwest is currently priced 26% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Des Moines to Chicago one-way?

    The cheapest airlines for a one-way flight from Des Moines to Chicago are Southwest ($89), Frontier ($98), and Allegiant Air ($171).

  • 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: Copa Airlines (97%), Avianca (95%), GoJet (92%).

  • 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 $1,252, our data indicates the cheapest price to be $157. The most popular route (Des Moines - Chicago O'Hare Intl), is priced around $177.

  • 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, August is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $245). Flying from Des Moines to Chicago in March is currently the most expensive (average of $321). 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 Des Moines?

Book flights to Des Moines if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Des Moines to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$181Average$243FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$267FlexibilityNo cancel feeOn-time69%

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