Cheap flights from Des Moines to Chicago from $416 DSM → ORD
Des Moines International Airport (DSM) → O'Hare International Airport (ORD)
The cheapest return found recently is $416 with American Airlines, 25 Aug 2027 – 4 Sept 2027, found 2 days ago.
- Cheapest return found recently
- $416, 25 Aug 2027 to 4 Sept 2027
- Usual return price
- $417 to $439
- Cheapest month to fly
- August 2027, return fares from $416 found in the last 7 days
Return
The cheapest return fare on each of 3 departure dates is usually $417 to $439.
Cheapest return found recently
$416
25 Aug 2027 – 4 Sept 2027 · American Airlines
Des Moines International Airport (DSM) → O'Hare International Airport (ORD)
Leaves 10:26 a.m. · Return leaves 8:26 a.m. · 3 h 9 min of travel, both ways together
out nonstop, back nonstop
found 2 days ago
Cheapest nonstop return
$416
25 Aug 2027 – 4 Sept 2027 · American Airlines
Des Moines International Airport (DSM) → O'Hare International Airport (ORD)
Leaves 10:26 a.m. · Return leaves 8:26 a.m. · 3 h 9 min of travel, both ways together
out nonstop, back nonstop
found 2 days ago
Found recently, and the cheapest we hold
$416 25 Aug 2027 – 4 Sept 2027found 2 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 29 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $234 to $428.
29 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 3 departure dates from 26 Nov to 25 Aug 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 10-night return fares leaving within 3 days of 25 Aug 2027 to compare.
Every date we hold
4 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 26 Nov – 30 Nov | $461 | Frontier Airlines | Des Moines International Airport (DSM) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 2 days ago | See prices for these dates |
| 13 Dec – 26 Dec | $417 | Frontier Airlines | Des Moines International Airport (DSM) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 2 days ago | See prices for these dates |
| 25 Aug 2027 – 4 Sept 2027 | $416 | American Airlines | Des Moines International Airport (DSM) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
Which month looks cheapest?
August 2027 is the cheapest month — from $416.
Airlines on the cheapest dates: Frontier Airlines, American Airlines.
Premium cabin fares from Des Moines to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 25 Aug 2027 – 4 Sept 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Des Moines to Chicago?
Return
Fares 14 to 29 days before departure were typically 34% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 11 Nov (29 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $356 | $234 | +52% | 12 |
| 7–13 days | $447 | $427 | +91% | 8 |
| 14–29 days | $234 | $234 | Cheapest seen | 11 |
| 30–59 days | $331 | $331 | +42% | 13 |
Live price for these dates
The cheapest return found recently is for 25 Aug 2027 – 4 Sept 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Des Moines to Chicago?
The cheapest return found recently is $416 with American Airlines, 25 Aug 2027 to 4 Sept 2027, found 2 days ago. The cheapest return fare on each of 3 departure dates is usually $417 to $439.
What is the cheapest month to fly from Des Moines to Chicago?
August 2027 is the cheapest month for a return, from $416, 25 Aug 2027 to 4 Sept 2027, found 2 days ago.
How far ahead should I book a flight from Des Moines to Chicago?
In 29 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 34% lower than 0 to 6 days before departure.
Is there a direct flight from Des Moines to Chicago?
Yes, the cheapest nonstop return found recently is $416 with American Airlines, 25 Aug 2027 to 4 Sept 2027, found 2 days ago.
Which airlines have the cheapest flights from Des Moines to Chicago?
Between 26 Nov and 25 Aug 2027, Frontier Airlines has the cheapest return on 2 of the 3 departure dates we hold, and American Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work