$88 Cheap Flights from Des Moines (DSM) to Chicago (ORD)

View $88 flight on Tue, Jul 8, 2025Opens in a new window
Find available prices by choosing your travel dates.

Cheap Flights from Des Moines to Chicago (DSM-ORD)

Prices were available within the past 7 days and start at $88 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, May 23 - Mon, May 26
DSM
Des Moines
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select United flight, departing Fri, May 23 from Des Moines to Chicago, returning Mon, May 26, priced at $189 just found
United
Sat, Jul 12 - Mon, Jul 14
DSM
Des Moines
ORD
Chicago
$193 Roundtrip, just found
$193
Roundtrip
just found
Select United flight, departing Sat, Jul 12 from Des Moines to Chicago, returning Mon, Jul 14, priced at $193 just found
United
Fri, May 16 - Sun, May 18
DSM
Des Moines
ORD
Chicago
$196 Roundtrip, found 14 hours ago
$196
Roundtrip
found 14 hours ago
Select United flight, departing Fri, May 16 from Des Moines to Chicago, returning Sun, May 18, priced at $196 found 14 hours ago
American Airlines
Fri, May 9 - Sun, May 11
DSM
Des Moines
ORD
Chicago
$199 Roundtrip, found 14 hours ago
$199
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Fri, May 9 from Des Moines to Chicago, returning Sun, May 11, priced at $199 found 14 hours ago
United
Fri, May 23 - Mon, May 26
DSM
Des Moines
ORD
Chicago
$208 Roundtrip, just found
$208
Roundtrip
just found
Select United flight, departing Fri, May 23 from Des Moines to Chicago, returning Mon, May 26, priced at $208 just found
Delta
Sat, Jul 12 - Mon, Jul 14
DSM
Des Moines
ORD
Chicago
$209 Roundtrip, just found
$209
Roundtrip
just found
Select Delta flight, departing Sat, Jul 12 from Des Moines to Chicago, returning Mon, Jul 14, priced at $209 just found
Southwest Airlines
Tue, Aug 19 - Wed, Sep 10
DSM
Des Moines
ORD
Chicago
$209 Roundtrip, just found
$209
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Aug 19 from Des Moines to Chicago, returning Wed, Sep 10, priced at $209 just found
United
Thu, Jun 26 - Sun, Jun 29
DSM
Des Moines
ORD
Chicago
$212 Roundtrip, found 6 hours ago
$212
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Jun 26 from Des Moines to Chicago, returning Sun, Jun 29, priced at $212 found 6 hours ago
United
Thu, Nov 13 - Mon, Nov 17
DSM
Des Moines
ORD
Chicago
$213 Roundtrip, found 4 hours ago
$213
Roundtrip
found 4 hours ago
Select United flight, departing Thu, Nov 13 from Des Moines to Chicago, returning Mon, Nov 17, priced at $213 found 4 hours ago
Delta
Thu, May 8 - Sat, May 17
DSM
Des Moines
ORD
Chicago
$214 Roundtrip, found 7 hours ago
$214
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, May 8 from Des Moines to Chicago, returning Sat, May 17, priced at $214 found 7 hours ago
Flights from Des Moines (DSM) to Chicago (ORD)
Origin airport
Des Moines Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$183
Distance
297 mi

Des Moines to Chicago Flights

The cheapest times to fly from Des Moines to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Des Moines to Chicago are during the month of May. You can find some of the cheapest flights from Des Moines to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Des Moines to Chicago

Sunday is one of the best days to book for cheap flights from Des Moines to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Des Moines to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Des Moines to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $88 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Des Moines to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Des Moines to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD) cost?
Cheap round-trip flights from Des Moines Intl. Airport (DSM) to O’Hare Intl. Airport (ORD) start from $189. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving DSM on May 16 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from DSM to ORD?
The cheapest flights from DSM to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
You can fly nonstop from Des Moines Intl. Airport (DSM) to O’Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from DSM to ORD?
Take off from DSM to ORD with United. This carrier currently has the cheapest one-way fare for this route, starting at $152. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from DSM on June 13 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
Every day, an average of 7 nonstop flights take off from Des Moines Intl. Airport (DSM) to O’Hare Intl. Airport (ORD). Choose the departure time that works for you.
What are the most popular departure times for flights from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
More passengers fly between DSM and ORD at 5 AM than at any other time of day. Looking to skip the crowds? Pick a flight outside the busiest times and there’s a chance you’ll save on your ticket as well.
What day of the week has the most flights from DSM to ORD?
Depart on a Friday if you’re searching for the biggest selection of flights from Des Moines Intl. Airport (DSM) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
The earliest flight out of Des Moines Intl. Airport (DSM) is at around 5:30AM UTC-6. Hop on this flight and you’ll reach O’Hare Intl. Airport (ORD) at approximately 7:02AM UTC-6. The total time in the air is 1h 32m.
How long does it take to fly from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
Flights from DSM to ORD have an average travel time of 1 hour and 34 minutes. The distance between the two airports is 300 mi.
What airline has the least delays from DSM to ORD?
With 85% of flights usually arriving as scheduled, Alaska Airlines has the best on-time performance for direct flights from Des Moines Intl. Airport (DSM) to O’Hare Intl. Airport (ORD). To check your flight status and receive notifications if anything changes, head to the Expedia App.
What is the best time to fly from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
To reach O’Hare Intl. Airport (ORD) without delays, choose a flight that leaves Des Moines Intl. Airport (DSM) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Des Moines Intl. Airport (DSM)?
If you’re taking a direct flight from Des Moines Intl. Airport (DSM) to Chicago, O’Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from DSM to ORD often results in higher prices. While you might find some last-minute deals, there’s no guarantee. Keep your travel plans flexible for a better chance of getting a bargain.
Is it cheaper to book a DSM to ORD flight and hotel package?
You’ll generally save money by securing a DSM to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage everything in one convenient place. After selecting your ideal accommodations and flights, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
If you booked your DSM to ORD flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

Explore a world of travel with Expedia

*Available to One Key members.