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Cheap Flights from Denver (DENA) to Chicago (MDW)

Compare Denver to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Denver to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Denver to Chicago Midway Airport? If you want to travel next month, return fares start from $254. Find the lowest prices on one-way and return tickets right here.
Chicago.$254 per passenger.Departing Tue, 5 May, returning Wed, 6 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Tue, 5 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 6 May, arriving in Denver International.Price includes taxes and charges.From $254, select.
Chicago.$254 per passenger.Departing Sat, 18 Apr, returning Tue, 21 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 18 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 21 Apr, arriving in Denver International.Price includes taxes and charges.From $254, select.
Chicago.$255 per passenger.Departing Mon, 27 Apr, returning Fri, 1 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Mon, 27 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 1 May, arriving in Denver International.Price includes taxes and charges.From $255, select.
Chicago.$283 per passenger.Departing Tue, 21 Apr, returning Tue, 28 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 21 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Apr, arriving in Denver International.Price includes taxes and charges.From $283, select.
Chicago.$283 per passenger.Departing Tue, 5 May, returning Tue, 5 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 5 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 May, arriving in Denver International.Price includes taxes and charges.From $283, select.
Chicago.$284 per passenger.Departing Sat, 30 May, returning Wed, 3 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 30 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 3 Jun, arriving in Denver International.Price includes taxes and charges.From $284, select.
Chicago.$284 per passenger.Departing Wed, 3 Jun, returning Wed, 10 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Wed, 3 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 10 Jun, arriving in Denver International.Price includes taxes and charges.From $284, select.
Chicago.$299 per passenger.Departing Thu, 28 May, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 28 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Denver International.Price includes taxes and charges.From $299, select.
Chicago.$304 per passenger.Departing Sat, 11 Jul, returning Wed, 15 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Sat, 11 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 15 Jul, arriving in Denver International.Price includes taxes and charges.From $304, select.
Chicago.$309 per passenger.Departing Sat, 18 Apr, returning Mon, 4 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Sat, 18 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 May, arriving in Denver International.Price includes taxes and charges.From $309, select.
Chicago.$325 per passenger.Departing Fri, 31 Jul, returning Sat, 1 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Fri, 31 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 1 Aug, arriving in Denver International.Price includes taxes and charges.From $325, select.
Chicago.$340 per passenger.Departing Mon, 30 Mar, returning Mon, 6 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 6 Apr, arriving in Denver International.Price includes taxes and charges.From $340, select.
Chicago.$346 per passenger.Departing Thu, 25 Jun, returning Thu, 2 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 25 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Jul, arriving in Denver International.Price includes taxes and charges.From $346, select.
Chicago.$361 per passenger.Departing Fri, 3 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Fri, 3 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in Denver International.Price includes taxes and charges.From $361, select.
Chicago.$366 per passenger.Departing Sat, 12 Sep, returning Mon, 14 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Denver International on Sat, 12 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 14 Sep, arriving in Denver International.Price includes taxes and charges.From $366, select.
Chicago.$369 per passenger.Departing Wed, 25 Mar, returning Sat, 28 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Wed, 25 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 28 Mar, arriving in Denver International.Price includes taxes and charges.From $369, select.

Find the cheapest month to fly from Denver to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Denver to Chicago Midway flights are currently cheapest in April.
Mar
from $369
Apr
from $254
May
from $254
Jun
from $284
Jul
from $304
Aug
from $373
Sep
from $366
Oct
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Nov
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Dec
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Jan
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Feb
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Direct flights from Denver to Chicago Midway

Denver to Chicago Midway: Alternative routes

Compare routes from Denver 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
Closest
from $254
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $130
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from $786
Search flights

Denver to Chicago: Flight information

The things to know before you go.
Cheapest flight found$254
Cheapest month to flyApril
Average flight time2 hrs, 23 mins
Most popular airlineSouthwest Airlines
Average flights per week96

Check out these Chicago hotels

Ready to plan your stay? Other travellers rate these Chicago hotels for cleanliness, service and location.
House 5863- Chicago's Premier Bed and Breakfast
12.62 km from city centre
$272
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1.45 km from city centre
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The Sono Chicago
3.50 km from city centre
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House 5863- Chicago's Premier Bed and Breakfast
12.62 km from city centre
$272
Per night
The St. Regis Chicago
1.45 km from city centre
$917
Per night
The Sono Chicago
3.50 km from city centre
$334
Per night
Explore top-rated hotels

Finding cheap flights from Denver to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Denver to Chicago Midway is $254. 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.
2 hours and 23 minutes is the average flight time from Denver to Chicago Midway.
Southwest Airlines and United fly direct from Denver to Chicago Midway.
As of March 2026, there are 96 flights per week flying from Denver to Chicago Midway.
The cheapest month to fly from Denver to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Denver to Chicago Midway Airport on Saturday, 18 April 2026.
Yes – the average flight time is 2 hours and 23 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.

How to find cheap flights to Chicago (MDW) from Denver (DENA) in 2024

Looking for cheap tickets from Denver to Chicago Midway? Return tickets start from $254 and one-way flights to Chicago Midway from Denver start from $126


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 British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets.
  • Compare flight deals to Chicago from Denver from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from $126 one-way.
  • Flex your dates to find the best DENA-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 Denver.
  • Set up a Price Alert. You can easily track the fare of your cheap flights by creating an alert. Whenever prices go down or up, 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 Denver and Chicago Midway? Make sure to tick '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
    United
  • Find the cheapest Business class flights from Denver 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 low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Denver 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 Denver and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Denver with hotels and car hire

Once you've secured your cheap flight ticket from Denver to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


Plan the rest of your trip from Denver to Chicago

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