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C$108 Cheap Flights from Des Moines to Chicago Midway

Compare Des Moines to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Des Moines Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Des Moines Airport to Chicago Midway Airport? If you want to travel next month, return fares start from C$246. Find the lowest prices on one-way and return tickets right here.
Chicago.C$108 per passenger.Departing Tue., Mar. 17.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Des Moines on Tue., Mar. 17, arriving in Chicago Midway.Price includes taxes and charges.From C$108, select.
Chicago.C$112 per passenger.Departing Sat., Apr. 25.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Sat., Apr. 25, arriving in Chicago Midway.Price includes taxes and charges.From C$112, select.
Chicago.C$135 per passenger.Departing Wed., May 20.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed., May 20, arriving in Chicago Midway.Price includes taxes and charges.From C$135, select.
Chicago.C$135 per passenger.Departing Thu., Mar. 26.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Thu., Mar. 26, arriving in Chicago Midway.Price includes taxes and charges.From C$135, select.
Chicago.C$146 per passenger.Departing Wed., Aug. 12.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed., Aug. 12, arriving in Chicago Midway.Price includes taxes and charges.From C$146, select.
Chicago.C$146 per passenger.Departing Tue., Jun. 2.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Tue., Jun. 2, arriving in Chicago Midway.Price includes taxes and charges.From C$146, select.
Chicago.C$149 per passenger.Departing Sat., Oct. 31.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Sat., Oct. 31, arriving in Chicago Midway.Price includes taxes and charges.From C$149, select.
Chicago.C$176 per passenger.Departing Wed., Jul. 1.One-way flight with Delta.Outbound indirect flight with Delta, departs from Des Moines on Wed., Jul. 1, arriving in Chicago Midway.Price includes taxes and charges.From C$176, select.
Chicago.C$176 per passenger.Departing Thu., Dec. 17.One-way flight with Delta.Outbound indirect flight with Delta, departs from Des Moines on Thu., Dec. 17, arriving in Chicago Midway.Price includes taxes and charges.From C$176, select.
Chicago.C$190 per passenger.Departing Wed., Jul. 1.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Des Moines on Wed., Jul. 1, arriving in Chicago Midway.Price includes taxes and charges.From C$190, select.
Chicago.C$287 per passenger.Departing Sun., Nov. 1.One-way flight with Delta.Outbound indirect flight with Delta, departs from Des Moines on Sun., Nov. 1, arriving in Chicago Midway.Price includes taxes and charges.From C$287, select.

Find the cheapest month to fly from Des Moines to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Des Moines to Chicago Midway flights are currently cheapest in March.
Mar.
from C$108
Apr.
from C$112
May
from C$135
Jun.
from C$146
Jul.
from C$176
Aug.
from C$146
Sep.
Find prices
Oct.
from C$149
Nov.
from C$287
Dec.
from C$176
Jan.
Find prices
Feb.
Find prices

Direct flights from Des Moines to Chicago Midway

Des Moines to Chicago Midway: Alternative routes

Compare routes from Des Moines to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from C$108
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Chicago O'Hare International

25km from central Chicago
from C$115
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Chicago Dupage County

51km from central Chicago
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Chicago Rockford

126km from central Chicago
from C$155
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Des Moines to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$108
Cheapest month to flyMarch
Average flight time1 hr, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week15

Finding cheap flights from Des Moines to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Des Moines to Chicago Midway is C$215. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 20 minutes is the average flight time from Des Moines to Chicago Midway.
Southwest Airlines flies direct from Des Moines to Chicago Midway.
As of March 2026, there are 15 flights per week flying from Des Moines to Chicago Midway.
The cheapest month to fly from Des Moines to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Des Moines Airport to Chicago Midway Airport on Tuesday, May 5, 2026.
Yes – the average flight time is 1 hour and 20 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago (MDW) from Des Moines (DSM) in 2026

Looking for cheap tickets from Des Moines to Chicago Midway? Round-trip tickets start from C$215 and one-way flights to Chicago Midway from Des Moines start from C$108

Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From American Airlines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Des Moines to Chicago Midway. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago from Des Moines from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from C$108 one-way.
  • Flex your dates to find the best DSM–MDW ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago Midway from Des Moines.
  • Set up a Price Alert. You can easily track the fare of your cheap Des Moines-Chicago Midway flights by creating an alert. Whenever prices go up or down, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Des Moines and Chicago Midway? Make sure to check "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results. Airlines that fly direct include: Southwest Airlines
  • Find the cheapest Business class flights from Des Moines and Chicago Midway. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute deal. Note that not all cabin classes are available for every destination or airline.
  • Flexible on when you travel? The cheapest month to fly from Des Moines to Chicago Midway is May.
  • Include nearby airports in your search. Widen your search for Des Moines to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
  • Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Des Moines and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Des Moines with hotels and car rental

Once you've secured your cheap flight ticket from Des Moines to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies all at once so you get the best car rental price for your trip.


Plan the rest of your trip from Des Moines to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.