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$61+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from Des Moines to Chicago are usually found in November or December, booked 89 days in advance, depart on a Thursday or Friday and return on a Friday

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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(United Airlines)

One-way from

$61
(Frontier)

Popular in

March

Cheapest in

November

Average price

$256
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
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From Des Moines to Chicago (CHI)
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One-way flight from Des Moines to Chicago (CHI)
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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 January 16, 2025.

This United Airlines deal was found by Cheapflights users on 1/16. 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 2/258:00 amDSM - ORD
Nonstop1h 28mUnited Airlines
Sat 3/17:52 pmORD - DSM
Nonstop1h 33mUnited Airlines
Deal found 1/16$189
This American Airlines deal was found by Cheapflights users on 1/16. 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.
Tue 2/412:15 pmDSM - ORD
Nonstop1h 28mAmerican Airlines
Sat 2/83:10 pmORD - DSM
Nonstop1h 24mAmerican Airlines
Deal found 1/16$194
This Delta deal was found by Cheapflights users on 1/16. 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 3/26:30 amDSM - MDW
1 stop6h 35mDelta
Tue 3/1110:25 amMDW - DSM
1 stop6h 02mDelta
Deal found 1/16$209
This Delta deal was found by Cheapflights users on 1/16. 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 3/210:32 amDSM - ORD
1 stop5h 41mDelta
Sun 3/96:15 amORD - DSM
1 stop4h 59mDelta
Deal found 1/16$209
This Southwest deal was found by Cheapflights users on 1/16. 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 2/64:50 pmDSM - MDW
1 stop4h 45mSouthwest
Sun 2/99:10 amMDW - DSM
1 stop3h 10mSouthwest
Deal found 1/16$229
This Southwest deal was found by Cheapflights users on 1/16. 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 2/48:30 amDSM - ORD
1 stop5h 55mSouthwest
Sat 2/811:05 amORD - DSM
1 stop8h 45mSouthwest
Deal found 1/16$239
This Mytrip deal was found by Cheapflights users on 1/15. 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.
Wed 2/123:40 pmDSM - ORD
1 stop8h 18mMultiple Airlines
Wed 2/195:15 amORD - DSM
2 stops18h 03mMultiple Airlines
Deal found 1/15$295
This Mytrip deal was found by Cheapflights users on 1/16. 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.
Wed 2/1910:00 amDSM - RFD
1 stop7h 46mAllegiant Air
Fri 2/2110:52 amRFD - DSM
1 stop11h 19mAllegiant Air
Deal found 1/16$369
This Mytrip deal was found by Cheapflights users on 1/16. 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.
Wed 2/193:40 pmDSM - RFD
3 stops29h 12mMultiple Airlines
Fri 2/2110:52 amRFD - DSM
1 stop11h 19mMultiple Airlines
Deal found 1/16$455

Find flights from Des Moines to Chicago within your budget

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 2/25

8:00 am-9:28 am

Nonstop1h 28m

Chicago O'Hare Intl

Sat 3/1

7:52 pm-9:25 pm

Nonstop1h 33m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 2/4

12:15 pm-1:43 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sat 2/8

3:10 pm-4:34 pm

Nonstop1h 24m

$194

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sun 3/2

6:30 am-1:05 pm

1 stop6h 35m

Chicago Midway

Tue 3/11

10:25 am-4:27 pm

1 stop6h 02m

$209

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sun 3/2

6:30 am-12:55 pm

1 stop6h 25m

Chicago O'Hare Intl

Tue 3/11

1:25 pm-5:19 pm

1 stop3h 54m

$209

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Thu 2/6

4:50 pm-9:35 pm

1 stop4h 45m

Chicago Midway

Sun 2/9

9:10 am-12:20 pm

1 stop3h 10m

$229

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 2/4

8:30 am-2:25 pm

1 stop5h 55m

Chicago O'Hare Intl

Sat 2/8

11:05 am-7:50 pm

1 stop8h 45m

$239

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 2/12

3:40 pm-11:58 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 2/19

5:15 am-11:18 pm

2 stops18h 03m

$295

Des MoinesChicago

DSM - RFD

DSMRFD

Des Moines

Wed 2/19

10:00 am-5:46 pm

1 stop7h 46m

Chicago Greater Rockford

Fri 2/21

10:52 am-10:11 pm

1 stop11h 19m

$369

Des MoinesChicago

DSM - RFD

DSMRFD

Des Moines

Wed 2/19

3:40 pm-8:52 pm

3 stops29h 12m

Chicago Greater Rockford

Fri 2/21

10:52 am-10:11 pm

1 stop11h 19m

$455

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 3/18

7:48 pm-9:05 am

1 stop13h 17m

Chicago O'Hare Intl

Sat 3/22

9:25 am-6:57 pm

1 stop9h 32m

$660

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 18 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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.

Travel insights for flights from Des Moines to Chicago

Get recent, data-driven insights about flights from Des Moines to Chicago including ideal travel times, pricing trends, and more.

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 January 10, 2025.

Booking 89 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 $320). 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 January 16, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 15% on flights from Des Moines to Chicago by exploring options for tickets at noon.

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 January 16, 2025.

The most flights from DSM to CHI are scheduled on a Wednesday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 January 16, 2025.
Read reviews from past customers who have flown United Airlines, American Airlines and Southwest from Des Moines to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 28 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 United Airlines. 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 $194 and $209 round-trip. United Airlines is currently priced 34% 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 Frontier ($61), Southwest ($105), and American Airlines ($214).

  • 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: Lufthansa (87%), Envoy Air (86%), Air Wisconsin (84%).

  • 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 $1,076, our data indicates the cheapest price to be $153. The most popular route (Des Moines - Chicago O'Hare Intl), is priced around $189.

  • 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$187Average$289FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$297FlexibilityNo cancel feeOn-time69%
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