Cheap Flights From Denver Intl. (DEN) To Midway Intl. (MDW)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

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

The cheapest flights to Midway Intl. found within the past 7 days were CA $321 round trip and CA $152 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $321 Roundtrip, found 5 days ago
CA $321
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $321 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $373 Roundtrip, found 5 days ago
CA $373
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $373 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $420 Roundtrip, found 5 days ago
CA $420
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $420 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $472 Roundtrip, found 5 days ago
CA $472
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $472 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $477 Roundtrip, found 5 days ago
CA $477
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $477 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $490 Roundtrip, found 5 days ago
CA $490
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $490 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $529 Roundtrip, found 5 days ago
CA $529
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $529 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $542 Roundtrip, found 5 days ago
CA $542
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $542 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $556 Roundtrip, found 5 days ago
CA $556
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $556 found 5 days ago
Fri, Feb 27 - Wed, May 13
DEN
Denver
MDW
Chicago
CA $576 Roundtrip, found 5 days ago
CA $576
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 27 from Denver to Chicago, returning Wed, May 13, priced at CA $576 found 5 days ago

Frequently asked questions

Are there direct flights from DIA airport to Midway Intl. Airport (MDW)?
The only thing standing between you and your next incredible adventure is a single flight. Southwest Airlines is the only air carrier that offers direct services from DEN to Midway Intl. Airport (MDW), so it's wise to book well in advance.
What airlines fly from DIA airport to Midway Airport?
Wanting to fly straight from Denver to Chicago? Southwest Airlines (WN) offers as many as 234 flights every month and is the number one choice for many seasoned travelers.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca 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 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Denver (DEN)

Travelers at DEN love to visit these top cities. Roam to the top destinations from Denver (DEN) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (MDW)

Travelers at MDW love to visit these top cities. Roam to the top destinations from Chicago(MDW) today with the cheap prices from Travelocity!

*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.