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

Compare Denver International 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 International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Denver International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $225. Find the lowest prices on one-way and return tickets right here.
Chicago.$225 per passenger.Departing Tue, 25 Aug, returning Sat, 3 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Tue, 25 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 3 Oct, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Tue, 6 Oct, returning Sat, 10 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Tue, 6 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 10 Oct, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Wed, 11 Nov, returning Thu, 12 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Wed, 11 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 12 Nov, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Mon, 24 Aug, returning Wed, 26 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Mon, 24 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 26 Aug, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Wed, 26 Aug, returning Tue, 1 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Wed, 26 Aug, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Sat, 12 Sep, returning Mon, 14 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 12 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 14 Sep, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Thu, 29 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 2 Nov, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$225 per passenger.Departing Thu, 24 Sep, returning Mon, 19 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Thu, 24 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 19 Oct, arriving in Denver International.Price includes taxes and charges.From $225, select.
Chicago.$294 per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 26 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 3 Dec, arriving in Denver International.Price includes taxes and charges.From $294, select.
Chicago.$294 per passenger.Departing Tue, 10 Nov, returning Tue, 17 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 10 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 17 Nov, arriving in Denver International.Price includes taxes and charges.From $294, select.
Chicago.$294 per passenger.Departing Wed, 7 Oct, returning Sat, 10 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Wed, 7 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 10 Oct, arriving in Denver International.Price includes taxes and charges.From $294, select.
Chicago.$294 per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 1 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Dec, arriving in Denver International.Price includes taxes and charges.From $294, select.
Chicago.$302 per passenger.Departing Fri, 30 Oct, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Fri, 30 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 9 Nov, arriving in Denver International.Price includes taxes and charges.From $302, select.
Chicago.$303 per passenger.Departing Thu, 28 Jan, returning Mon, 1 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 28 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Feb, arriving in Denver International.Price includes taxes and charges.From $303, select.
Chicago.$303 per passenger.Departing Sat, 22 Aug, returning Mon, 24 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Sat, 22 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 24 Aug, arriving in Denver International.Price includes taxes and charges.From $303, select.
Chicago.$303 per passenger.Departing Mon, 7 Sep, returning Wed, 9 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Mon, 7 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 9 Sep, arriving in Denver International.Price includes taxes and charges.From $303, select.

Find the cheapest month to fly from Denver International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Denver International to Chicago Midway flights are currently cheapest in August.
Aug
from $225
Sep
from $225
Oct
from $225
Nov
from $225
Dec
from $294
Jan
from $390
Feb
Find prices
Mar
from $425
Apr
from $423
May
from $545
Jun
Find prices
Jul
Find prices

Direct flights from Denver International to Chicago Midway

Denver International to Chicago Midway: Alternative routes

Compare routes from Denver International 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 $225
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $167
Search flights

Chicago Rockford

127km from central Chicago
from $386
Search flights

Denver to Chicago: Flight information

The things to know before you go.
Cheapest flight found$225
Cheapest month to flyAugust
Average flight time2 hrs, 21 mins
Most popular airlineSouthwest Airlines
Average flights per week45

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

The best price we found for a return flight from Denver International to Chicago Midway is $225. 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 21 minutes is the average flight time from Denver International to Chicago Midway.
Southwest Airlines flies direct from Denver International to Chicago Midway.
As of August 2026, there are 45 flights per week flying from Denver International to Chicago Midway.
The cheapest month to fly from Denver International to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Denver International Airport to Chicago Midway Airport on Wednesday, 26 August 2026.
Yes – the average flight time is 2 hours and 21 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, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Denver International Airport (DEN) to Chicago Midway Airport (MDW): what you need to know

  • The average duration of a direct flight from Denver International Airport to Chicago Midway Airport is 2 hours 25 minutes.

  • Chicago is one hour ahead of Denver and follows the UTC-6 timezone.

  • Flights from DEN to MDW start at 05:00 — the earliest with Southwest Airlines. The last service of the day is at 21:55 with Southwest Airlines. In total, there are 26 weekly Denver International Airport to Chicago Midway Airport flights.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Make sure you're at the airport on time to board your DEN to MDW flight.

  • You'll likely experience longer queues during popular months such as July. Arriving up to four hours in advance for an international flight and two hours for a domestic departure will help ensure a smooth travel experience.

  • Southwest Airlines is your gateway to exploring Chicago (and perhaps some other great corners of the United States!). Browse the direct flights from Denver International Airport to Chicago Midway Airport offered by this popular airline.

  • The majority of passengers choose to travel with Southwest Airlines on this route.

  • Frontier Airlines stands out as the most punctual carrier for DEN to MDW flights, with 90.91% of its services reaching their destination on schedule.

  • Consider adding a stopover when booking your ticket from Denver International Airport to Chicago Midway Airport. Just deselect 'Direct flights only' to break up your trip, or perhaps see a new city along the way. Here are some options between DEN and MDW:

    • Minneapolis St Paul Airport

    • St Louis Airport

    • Kansas City International Airport

How to find the cheapest flights from Denver International Airport (DEN) to Chicago Midway Airport (MDW)

  • The lowest price we've seen for a one-way Denver International Airport to Chicago Midway Airport flight is $112. A return fare right now is $225. Depending on the availability and when you book, these fares can change.

  • Don't leave things to the last moment. You're more likely to find cheap tickets from DEN to MDW if you book in advance. Airlines often offer some amazing early bird deals.

  • The cheapest month for flights from Denver International Airport to Chicago Midway Airport is May. Use the 'Whole month' tool to find the lowest airfares if you have a flexible travel schedule.

  • You won't have to check every day to find out if fares have gone down when you set up a Price Alert. We'll notify you the moment a special offer becomes available on cheap flights from DEN to MDW.

  • Choose your ideal arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Denver International Airport to Chicago Midway Airport.

Handy information about Denver International Airport (DEN)

  • DEN's address is 8500 Pena Boulevard.

  • Denver International Airport earns top marks for its on-time performance. 80% of flights that depart DEN reach their destination on time.

  • Denver International Airport is about 40 kilometres from central Denver. If you're driving, catching a taxi or ride-sharing from the centre, it'll take you 35 minutes or so to get there, depending on the traffic.

  • Expect a journey time of around 35 minutes on public transport.

  • Get your flight from Denver International Airport to Chicago Midway Airport off to a relaxed start. Just a quick ride from DEN, spend the night in Baymont by Wyndham Denver International Airport and you'll be well-rested for the trip ahead.

Arriving at Chicago Midway Airport (MDW)

  • If you're arriving on a late Denver International Airport to Chicago Midway Airport flight, few things top the convenience of being near the terminal. Collect your bags from the carousel and then be resting shortly after at one of these options near MDW:

  • Get your adventure underway by picking up a Chicago Midway Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.

  • Lock in the best rate by reserving your ride from Chicago Midway Airport about four weeks in advance of your trip.

When to fly to Chicago Midway Airport (MDW)

  • It's time to plan your travel dates for your flight from Denver International Airport to Chicago Midway Airport. July is the most popular month to visit Chicago. If you want a more laid-back vibe, go in December.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your flights from Denver International Airport to Chicago Midway Airport in this month if you enjoy this type of weather.

  • Search for cheap tickets from DEN to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of the United States

  • You've visited Chicago, now it's time to discover other parts of the United States. Travel around 451 kilometres south-east to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you on the go.

  • Indianapolis is another well-known destination in the United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan smart, explore more

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Prices shown on this page are estimated lowest prices only. Found in the last 12 days.