Cheap Flights from Denver International to Chicago Midway

Compare Denver International to Chicago Midway flight deals

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Flight deals from Denver International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Denver International to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

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 January.

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.

Denver to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,069
Cheapest month to flyJanuary
Average flight time2 hrs, 23 mins
Most popular airlineSouthwest Airlines
Average flights per week40

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 R 1,788. 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 International to Chicago Midway.
Southwest Airlines, Frontier Airlines and Volaris fly direct from Denver International to Chicago Midway.
As of December 2025, there are 40 flights per week flying from Denver International to Chicago Midway.
The cheapest month to fly from Denver International to Chicago Midway is usually January.
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 Friday, 16 January 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.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

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

  • The average time for a direct flight from Denver International Airport to Chicago Midway International Airport is 2 hours 20 minutes.

  • Chicago's timezone is UTC-5, which makes Chicago one hour ahead of Denver.

  • Choose from 50 weekly Denver International Airport to Chicago Midway International Airport flights. The 05:10 departure with Southwest Airlines is the earliest available. Southwest Airlines operates the latest service of the day at 22:10.

  • Your DEN to MDW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • You'll likely experience longer lines during popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a good idea.

  • Frontier Airlines has direct flights from Denver International Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of United States if time allows.

  • The airline that passengers book most often on this route is Frontier Airlines.

  • Southwest Airlines is a leader in on-time performance for DEN to MDW flights, with 81.77% of services landing on schedule.

  • Think about adding a stopover when booking your ticket from Denver International Airport to Chicago Midway International Airport. Simply uncheck 'Direct flights only' to break up your trip, or enjoy a detour to a new and interesting place. Check out these options between DEN and MDW:

    • Kansas City International Airport

    • Lambert-St. Louis International Airport

    • Minneapolis-St. Paul International Airport

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

  • R 1,069 is currently the best price for a one-way Denver International Airport to Chicago Midway International Airport flight. Return flights start at R 1,784. These prices may change based on availability.

  • Book six months before you travel. After looking at the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from DEN to MDW.

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

  • Snapping up cheap flights from DEN to MDW is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you as soon as a lower fare pops up.

  • Tailor your trip using filters. Select your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from Denver International Airport to Chicago Midway International Airport.

Handy information about Denver International Airport (DEN)

  • The address for DEN is 8500 Pena Boulevard.

  • Denver International Airport maintains a strong on-time performance, making delays less likely. Departures from DEN land on schedule 80.23% of the time.

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

  • Taking public transport? You can expect a journey time of around 1 hour 30 minutes.

  • Booking a night at a hotel can take the stress out of reaching the airport on time. If you want a place to stay before your flight from Denver International Airport to Chicago Midway International Airport, have a look at Baymont by Wyndham Denver International Airport. It's a quick drive from DEN.

Arriving at Chicago Midway International Airport (MDW)

  • If you're coming in on a late Denver International Airport to Chicago Midway International Airport flight, nothing tops the convenience of being close to the terminal. Grab your bags from the carousel and then be showered and relaxing not long after at one of these hotels near MDW:

  • Travel at your own pace with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and find adventure across Chicago and beyond.

  • Reserving your vehicle from Chicago Midway International Airport about four weeks ahead can help you secure the lowest rate.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The street address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • When travelling by public transport, expect a journey of about 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Denver International Airport to Chicago Midway International Airport is May, while July is the busiest. Choose the best time to go to Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • When reserving your flight from Denver International Airport to Chicago Midway International Airport, consider the type of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • 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 United States

  • You've seen Chicago, now it's time to explore other parts of United States. Travel around 451 kilometres south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • If you're ready to explore another corner of United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key reasons to visit.

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