$76 Cheap Flights from Denver to Chicago

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Find The Best Dates To Fly from Denver Intl. to Midway Intl.

Amazing DEN to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $145 round trip and $76 one way. Prices and availability subject to change. Additional terms may apply.

FAQs about flights from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)

Can I catch a flight from Denver, CO Airport (DEN-Denver Intl.) to Chicago, IL Airport (MDW-Midway Intl.) right now?

It's wise to know about any travel advice reports and quarantine requirements in place in your destination. Make sure you go to our Covid-19 Travel Advisor for up-to-date information on booking a flight to Chicago, IL Airport (MDW-Midway Intl.).

Are there direct flights from DIA airport to Midway Airport?

You'll have trouble finding a flight straight from Denver Airport to MDW, but there's no need to stress. Delta, Aeromexico and KLM operate flights with only one stopover.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Chicago, IL Airport (MDW-Midway Intl.), please visit our Customer Service Portal.

How long is the flight from Denver Intl. Airport (DEN) to Chicago Airport?

If you were planning to drift into a long and blissful slumber during your Denver to Chicago journey, you'll have to rethink those plans. The average flight time between DEN and Midway Airport is a short 2 hours and 21 minutes — just enough to sit back and rest your eyes for a short while.

What is the flight distance from Denver Airport to Midway Airport?

Between Denver Intl. Airport (DEN) and Chicago Airport, the flight distance is about 1,740 mi. So, order a glass of wine and get comfortable. You've got some important decisions to make — watch a new series, dive into your novel or catch up on your beauty sleep?

What airlines fly from Denver Intl. Airport (DEN) to Chicago Airport?

You'll have to make at least one stopover if you're flying from DIA airport to Chicago Airport, as no airlines offer direct flights between these destinations. Make the most of your layover time by stretching your legs, freshening up and checking out what the stores have on offer.

What airlines have practices regarding COVID-19 in place and use social distancing?

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2020. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Sunday, as data shows the end of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2020, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 2 months prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2020 saved nearly 40% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.com from January to December 2020. Savings are subject to change based on departure location, date and destination.


Traveling From Denver Intl.
Traveling To Midway Intl.
Shortest Flight Time 4 hours 15 mins
Earliest Departure Time 6:00AM CST
Latest Departure Time 9:05PM CST
Lowest Flight Price $145

Route Info

Flight path for flights from Denver International Airport to Chicago Midway International Airport.

898.00 miles

Discover our best flights from Denver DEN to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 


Find our best return flights from Denver DEN to Chicago MDW at the right price  

Airfares to Chicago MDW from Denver DEN currently cost between $145 and $184. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 


Book one-way flights from Denver DEN to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Denver DEN to Chicago MDW on Travelocity starting at $76. Prices and availability subject to change. Additional terms may apply. 


Get to Chicago MDW from Denver DEN quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from DEN to take around 4 hour(s) 15 min(s).  


Find our cheapest airfares for flights from Denver DEN to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from DEN. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  


Get our best airfare deals for your flight from Denver DEN to Chicago MDW today 

If you’re flexible about when you travel, January is usually the cheapest month to fly from Denver DEN to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 


Book flexible airline tickets for flights to Chicago MDW from Denver DEN 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from DEN have this option.  


Travel with confidence when you book flights to Chicago MDW from Denver DEN with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.