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

View AU$168 flight on Sat, 20 Sep. 2025Opens in a new window

Popular airlines from Denver International Airport (DEN) to Chicago Midway Airport (MDW)

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

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

Delta
Wed, 15 Oct. - Wed, 22 Oct.
DEN
Denver
MDW
Chicago
AU$411 Return, found 4 hours ago
AU$411
Return
found 4 hours ago
Select Delta flight, departing Wed, 15 Oct. from Denver to Chicago, returning Wed, 22 Oct., priced at AU$411 found 4 hours ago
Delta
Wed, 15 Oct. - Wed, 22 Oct.
DEN
Denver
MDW
Chicago
AU$488 Return, found 4 hours ago
AU$488
Return
found 4 hours ago
Select Delta flight, departing Wed, 15 Oct. from Denver to Chicago, returning Wed, 22 Oct., priced at AU$488 found 4 hours ago
Delta
Wed, 15 Oct. - Wed, 22 Oct.
DEN
Denver
MDW
Chicago
AU$489 Return, found 4 hours ago
AU$489
Return
found 4 hours ago
Select Delta flight, departing Wed, 15 Oct. from Denver to Chicago, returning Wed, 22 Oct., priced at AU$489 found 4 hours ago
Delta
Sat, 11 Oct. - Sat, 18 Oct.
DEN
Denver
MDW
Chicago
AU$491 Return, found 4 days ago
AU$491
Return
found 4 days ago
Select Delta flight, departing Sat, 11 Oct. from Denver to Chicago, returning Sat, 18 Oct., priced at AU$491 found 4 days ago
Delta
Wed, 15 Oct. - Wed, 22 Oct.
DEN
Denver
MDW
Chicago
AU$518 Return, found 4 hours ago
AU$518
Return
found 4 hours ago
Select Delta flight, departing Wed, 15 Oct. from Denver to Chicago, returning Wed, 22 Oct., priced at AU$518 found 4 hours ago
Delta
Sat, 11 Oct. - Sat, 18 Oct.
DEN
Denver
MDW
Chicago
AU$559 Return, found 4 days ago
AU$559
Return
found 4 days ago
Select Delta flight, departing Sat, 11 Oct. from Denver to Chicago, returning Sat, 18 Oct., priced at AU$559 found 4 days ago
Delta
Wed, 15 Oct. - Wed, 22 Oct.
DEN
Denver
MDW
Chicago
AU$565 Return, found 4 hours ago
AU$565
Return
found 4 hours ago
Select Delta flight, departing Wed, 15 Oct. from Denver to Chicago, returning Wed, 22 Oct., priced at AU$565 found 4 hours ago
Delta
Tue, 14 Oct. - Thu, 16 Oct.
DEN
Denver
MDW
Chicago
AU$592 Return, found 6 days ago
AU$592
Return
found 6 days ago
Select Delta flight, departing Tue, 14 Oct. from Denver to Chicago, returning Thu, 16 Oct., priced at AU$592 found 6 days ago
Delta
Sat, 11 Oct. - Sat, 18 Oct.
DEN
Denver
MDW
Chicago
AU$599 Return, found 4 days ago
AU$599
Return
found 4 days ago
Select Delta flight, departing Sat, 11 Oct. from Denver to Chicago, returning Sat, 18 Oct., priced at AU$599 found 4 days ago
Delta
Tue, 14 Oct. - Thu, 16 Oct.
DEN
Denver
MDW
Chicago
AU$625 Return, found 6 days ago
AU$625
Return
found 6 days ago
Select Delta flight, departing Tue, 14 Oct. from Denver to Chicago, returning Thu, 16 Oct., priced at AU$625 found 6 days ago

Find the cheapest month to fly from Denver (DEN) to Chicago (MDW)

March is typically the cheapest month to fly

From AU$74 - AU$360 per traveller.

Graph displaying average flight prices per month

Flight from Denver to Chicago route information
Origin airport
Denver Intl.
Destination airport
Midway Intl.
Return price
AU$410
Distance
1430 km
Average flight time
3 hours 28 mins

Your quick guide to flights from Denver to Chicago

Pick up great flights from Denver to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Denver to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Denver to Chicago that take around hours.

Find cheap flights from Denver to Chicago

From the great flight deals with prices currently ranging from AU$411 to AU$625, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Denver to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in October.

Reasons to book your flight from Denver to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Denver to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Frequently asked questions

How much is a flight from DIA airport to Midway Airport?
Pack your bags, because round-trip journeys from Denver Airport to Midway Intl. Airport (MDW) start from AU$411. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from DIA airport to Chicago Airport?
We get that life can throw the odd curveball, so we've made it as hassle-free as possible for you to cancel your trip online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from DIA airport to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from DIA airport to Midway Airport?
With a flight distance of 1 450 kilometres, it's just a hop from DIA airport to MDW. It might be a quick one, but it's still worth bringing along a book to read.
Which airlines fly direct from DEN to Chicago Airport?
There are several airlines that fly from Denver Airport to MDW. Southwest Airlines (WN) is a top choice, offering 260 flights on this route each month. Another airline operating on this route is Frontier Airlines (F9). You'll have 47 flights each month to select from.
Are DIA airport to Midway Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a great last-minute deal from DEN to MDW, but it's also possible to miss out entirely! As many airlines advertise prices up to 12 months in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you see a bargain. Expedia compares carrier prices and updates flight deals all the time, so you can be sure you're always seeing the latest offers.

Explore a world of travel with Expedia

Chicago Flight Deals

Chicago

Denver to O'Hare Intl.
AU$220.10
*Available to Expedia members.