$552 Cheap Flights from Durango (DRO) to Chicago (MDW)

View $552 flight on Wed, Nov 12, 2025Opens in a new window

Popular airlines from Durango–La Plata County Airport (DRO) to Chicago Midway Airport (MDW)

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Cheap Flights from Durango to Chicago (DRO-MDW)

Prices were available within the past 7 days and start at $552 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $368
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $368

Frequently asked questions

How much does a flight from La Plata County Airport (DRO) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $552 or cheap return flight from La Plata County Airport (DRO) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from La Plata County Airport (DRO) to Midway Intl. Airport (MDW)?
The cheapest month to fly from DRO to MDW is , when demand is low. Off-peak season is generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from La Plata County Airport (DRO) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest DRO to MDW flight.
How many flights per day from La Plata County Airport (DRO) to Midway Intl. Airport (MDW)?
You'll have to take a flight with a layover when traveling from La Plata County Airport (DRO) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from DRO to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from La Plata County Airport (DRO) to Midway Intl. Airport (MDW)?
To avoid potential delays on the La Plata County Airport (DRO) to Midway Intl. Airport (MDW) route, fly before 3 PM. Departures after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from La Plata County Airport (DRO) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book your flight from DRO to MDW often results in higher prices. While you might find some last-minute deals, they're not always guaranteed. Be flexible with your itinerary for a better chance of getting a bargain.
Is it cheaper to book a DRO to MDW flight and hotel package?
Booking a DRO to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our wide range of hotels and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from La Plata County Airport (DRO) to Midway Intl. Airport (MDW)?
In most instances, you can modify or cancel your DRO to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you need more information, visit our Customer Service portal.

Travel information

Travel information

Origin airport
La Plata County
Destination airport
Midway Intl.
Distance
1111 mi

Book with confidence

Book with confidence

Durango to Chicago Flights

The cheapest times to fly from Durango to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Durango to Chicago are during the month of . You can find some of the cheapest flights from Durango to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Durango to Chicago

Sunday is one of the best days to book for cheap flights from Durango to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Durango to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Durango to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $552 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Durango to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Durango to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Durango to Chicago Flights

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