HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$65+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Des Moines to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Thursday or Friday 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 September 15, 2025.

Round-trip from

$189
(American Airlines)

One-way from

$65
(Southwest)

Popular in

October

Cheapest in

May

Average price

$224

Good round-trip deal

$346 or less

Good one-way deal

$220 or less
From Des Moines to Chicago (CHI)
Search Deals
One-way flight from Des Moines to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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

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 September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:32 pmDSM - ORD
1 stop9h 44mFrontier
Sun 11/25:00 amORD - DSM
1 stop7h 47mFrontier
Deal found 9/13$189
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:00 amDSM - ORD
Nonstop1h 33mAmerican Airlines
Tue 11/48:38 pmORD - DSM
Nonstop1h 30mAmerican Airlines
Deal found 9/13$190
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:00 amDSM - ORD
Nonstop1h 27mAmerican Airlines
Thu 11/67:00 amORD - DSM
Nonstop1h 32mAmerican Airlines
Deal found 9/15$191
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:16 amDSM - ORD
Nonstop1h 33mAmerican Airlines
Thu 10/1610:00 pmORD - DSM
Nonstop1h 23mAmerican Airlines
Deal found 9/13$194
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2811:06 amDSM - MDW
1 stop6h 37mDelta
Tue 11/49:20 amMDW - DSM
1 stop4h 39mDelta
Deal found 9/13$197
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:05 amDSM - ORD
1 stop6h 35mDelta
Tue 11/46:08 amORD - DSM
1 stop4h 18mDelta
Deal found 9/13$197
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:08 amDSM - ORD
Nonstop1h 31mAmerican Airlines
Mon 9/2910:06 pmORD - DSM
Nonstop1h 22mAmerican Airlines
Deal found 9/13$199
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/302:32 pmDSM - ORD
2 stops16h 54mFrontier
Thu 11/66:00 amORD - DSM
1 stop7h 47mFrontier
Deal found 9/14$201
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/214:45 pmDSM - MDW
1 stop5h 20mSouthwest
Thu 10/236:55 pmMDW - DSM
1 stop4h 35mSouthwest
Deal found 9/15$203
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/262:25 pmDSM - ORD
1 stop9h 34mFrontier
Sun 9/286:00 amORD - DSM
1 stop7h 40mFrontier
Deal found 9/14$207
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:50 pmDSM - MDW
1 stop3h 15mSouthwest
Sun 10/56:50 amMDW - DSM
1 stop4h 35mSouthwest
Deal found 9/13$209
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amDSM - ORD
1 stop6h 35mDelta
Thu 10/166:08 amORD - DSM
1 stop4h 18mDelta
Deal found 9/13$214

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 September 15, 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 - ORD

DSMORD

Des Moines

Thu 10/30

5:00 am-6:27 am

Nonstop1h 27m

Chicago O'Hare Intl

Sun 11/2

7:00 am-8:32 am

Nonstop1h 32m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 10/17

5:00 am-6:27 am

Nonstop1h 27m

Chicago O'Hare Intl

Mon 10/20

6:55 am-8:22 am

Nonstop1h 27m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 12/17

5:01 pm-6:53 pm

Nonstop1h 52m

Chicago O'Hare Intl

Wed 1/21

2:50 pm-4:14 pm

Nonstop1h 24m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Thu 10/30

7:30 am-9:05 am

Nonstop1h 35m

Chicago O'Hare Intl

Thu 11/6

11:46 am-1:16 pm

Nonstop1h 30m

$191

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 10/3

6:36 pm-8:10 pm

Nonstop1h 34m

Chicago O'Hare Intl

Sun 10/5

9:05 am-10:32 am

Nonstop1h 27m

$194

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Thu 10/2

7:08 am-8:39 am

Nonstop1h 31m

Chicago O'Hare Intl

Sun 10/5

6:45 am-8:09 am

Nonstop1h 24m

$194

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 10/28

11:06 am-5:43 pm

1 stop6h 37m

Chicago Midway

Tue 11/4

9:20 am-1:59 pm

1 stop4h 39m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Wed 10/29

11:06 am-5:43 pm

1 stop6h 37m

Chicago Midway

Wed 11/5

9:20 am-1:59 pm

1 stop4h 39m

$197

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 12/17

2:54 pm-9:40 pm

1 stop6h 46m

Chicago O'Hare Intl

Wed 1/21

6:00 am-10:22 am

1 stop4h 22m

$197

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 10/29

10:00 am-4:11 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 11/5

8:57 am-1:59 pm

1 stop5h 02m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 47 results
1
2
3
...
5

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 September 12, 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 September 15, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 78% on flights from Des Moines to Chicago by exploring options for tickets in the evening.

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 September 15, 2025.

The most flights from DSM to CHI are scheduled on a Monday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 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 September 15, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 36 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 American Airlines, United Airlines, and Delta fly from Des Moines to Chicago in about 1h 27m. The time it takes to get you to your destination can typically vary by up to 5h 10m. Airlines will cover a distance of 298 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 $189 on this airline. An additional option worth looking into is United Airlines, starting at $189. American Airlines is currently priced 25% 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 ($70), Frontier ($98), and Delta ($99).

  • 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: GoJet (100%), Avianca (84%), Qatar Airways (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 $1,013, our data indicates the cheapest price to be $125. 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 $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 Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Des Moines to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Omaha to O'Hare Intl flights
Des Moines to O'Hare Intl flights
Omaha to Midway flights
Des Moines to Midway flights
Cedar Rapids to O'Hare Intl flights
Moline to O'Hare Intl flights
Omaha to St. Louis flights
Sioux City to O'Hare Intl flights
Des Moines to St. Louis flights
Mason City to O'Hare Intl flights
Dubuque to O'Hare Intl flights
Cedar Rapids to Midway flights
Omaha to Evansville flights
Omaha to Rockford flights
Omaha to Moline flights
La Crosse to O'Hare Intl flights
Burlington to O'Hare Intl flights
Omaha to Bloomington flights
Moline to Midway flights
Waterloo to O'Hare Intl flights
Des Moines to Rockford flights
La Crosse to St. Louis flights
La Crosse to Midway flights
Moline to Peoria flights
La Crosse to Peoria flights
Waterloo to St. Louis flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$245FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$254FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.