$99 Cheap Flights from Des Moines (DSM) to Chicago (ORD)

View $99 flight on Tue, Oct 7, 2025Opens in a new window

Popular airlines from Des Moines International Airport (DSM) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $99 for one-way flights and $159 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 23 - Thu, Jan 8
DSM
Des Moines
ORD
Chicago
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Dec 23 from Des Moines to Chicago, returning Thu, Jan 8, priced at $159 found 5 days ago
Delta
Tue, Sep 9 - Sat, Sep 27
DSM
Des Moines
ORD
Chicago
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 9 from Des Moines to Chicago, returning Sat, Sep 27, priced at $174 found 6 days ago
Frontier Airlines
Wed, Oct 8 - Wed, Oct 15
DSM
Des Moines
ORD
Chicago
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Oct 8 from Des Moines to Chicago, returning Wed, Oct 15, priced at $188 found 4 days ago
United
Tue, Oct 7 - Tue, Oct 21
DSM
Des Moines
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select United flight, departing Tue, Oct 7 from Des Moines to Chicago, returning Tue, Oct 21, priced at $189 just found
American Airlines
Tue, Oct 7 - Tue, Oct 21
DSM
Des Moines
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 7 from Des Moines to Chicago, returning Tue, Oct 21, priced at $189 just found
United
Sat, Nov 15 - Sun, Nov 16
DSM
Des Moines
ORD
Chicago
$193 Roundtrip, found 3 hours ago
$193
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Nov 15 from Des Moines to Chicago, returning Sun, Nov 16, priced at $193 found 3 hours ago
United
Fri, Nov 14 - Sat, Nov 15
DSM
Des Moines
ORD
Chicago
$194 Roundtrip, found 3 hours ago
$194
Roundtrip
found 3 hours ago
Select United flight, departing Fri, Nov 14 from Des Moines to Chicago, returning Sat, Nov 15, priced at $194 found 3 hours ago
American Airlines
Sat, Sep 13 - Tue, Sep 16
DSM
Des Moines
ORD
Chicago
$194 Roundtrip, found 6 hours ago
$194
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Sep 13 from Des Moines to Chicago, returning Tue, Sep 16, priced at $194 found 6 hours ago
Southwest Airlines
Tue, Oct 7 - Tue, Oct 21
DSM
Des Moines
ORD
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Oct 7 from Des Moines to Chicago, returning Tue, Oct 21, priced at $197 just found
United
Tue, Nov 25 - Sat, Nov 29
DSM
Des Moines
ORD
Chicago
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select United flight, departing Tue, Nov 25 from Des Moines to Chicago, returning Sat, Nov 29, priced at $198 found 4 days ago

Find the cheapest month to fly from Des Moines (DSM) to Chicago (ORD)

October is typically the cheapest month to fly

From $138 - $314 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $309
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $309
Flights from Des Moines (DSM) to Chicago (ORD)
Origin airport
Des Moines Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, Southwest Airlines, United
Roundtrip price
$158
Distance
297 mi
Average flight time
1 hour 31 mins

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 December. 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 $99 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?
Snag a cheap one-way flight from $99 or cheap return flight from $159 from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from DSM to ORD is December, when demand is low. Off-peak season is usually when you'll find cheap fares for travel between these airports.
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 Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD)?
American Airlines and United Airlines are some well-known airlines offering reasonable fares. Keep in mind that flight prices from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD) can vary depending on departure dates, demand and how early you book. With Expedia's search tool, you can easily find a DSM to ORD flight that fits your preferences and budget.
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.

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*Available to One Key members.