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

View AU$142 flight on Mon, 17 Aug 2026Opens in a new window

Flight 1

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
Mon, 12 Oct - Tue, 13 Oct
DEN
Denver
MDW
Chicago
AU$284 Return, found 6 days ago
AU$284
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Oct from Denver to Chicago, returning Tue, 13 Oct, priced at AU$284 found 6 days ago
Delta
Sat, 22 Aug - Tue, 25 Aug
DEN
Denver
MDW
Chicago
AU$324 Return, found 1 day ago
AU$324
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from Denver to Chicago, returning Tue, 25 Aug, priced at AU$324 found 1 day ago
Delta
Sat, 22 Aug - Tue, 25 Aug
DEN
Denver
MDW
Chicago
AU$325 Return, found 1 day ago
AU$325
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from Denver to Chicago, returning Tue, 25 Aug, priced at AU$325 found 1 day ago
Delta
Mon, 12 Oct - Tue, 13 Oct
DEN
Denver
MDW
Chicago
AU$342 Return, found 6 days ago
AU$342
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Oct from Denver to Chicago, returning Tue, 13 Oct, priced at AU$342 found 6 days ago
Delta
Sat, 22 Aug - Tue, 25 Aug
DEN
Denver
MDW
Chicago
AU$377 Return, found 1 day ago
AU$377
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from Denver to Chicago, returning Tue, 25 Aug, priced at AU$377 found 1 day ago
Delta
Sat, 22 Aug - Tue, 25 Aug
DEN
Denver
MDW
Chicago
AU$382 Return, found 1 day ago
AU$382
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from Denver to Chicago, returning Tue, 25 Aug, priced at AU$382 found 1 day ago
Delta
Wed, 26 Aug - Wed, 2 Sept
DEN
Denver
MDW
Chicago
AU$383 Return, found 2 days ago
AU$383
Return
found 2 days ago
Select Delta flight, departing Wed, 26 Aug from Denver to Chicago, returning Wed, 2 Sept, priced at AU$383 found 2 days ago
Delta
Mon, 12 Oct - Tue, 13 Oct
DEN
Denver
MDW
Chicago
AU$385 Return, found 6 days ago
AU$385
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Oct from Denver to Chicago, returning Tue, 13 Oct, priced at AU$385 found 6 days ago
Delta
Mon, 12 Oct - Tue, 13 Oct
DEN
Denver
MDW
Chicago
AU$386 Return, found 6 days ago
AU$386
Return
found 6 days ago
Select Delta flight, departing Mon, 12 Oct from Denver to Chicago, returning Tue, 13 Oct, priced at AU$386 found 6 days ago
Delta
Sat, 22 Aug - Tue, 25 Aug
DEN
Denver
MDW
Chicago
AU$390 Return, found 1 day ago
AU$390
Return
found 1 day ago
Select Delta flight, departing Sat, 22 Aug from Denver to Chicago, returning Tue, 25 Aug, priced at AU$390 found 1 day ago

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 centre is 23 minutes. Flights from AU$647
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from AU$647

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

January is typically the cheapest month to fly

From AU$84 - AU$347 per traveller.

Frequently asked questions

How much does a flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from DEN to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when DEN to MDW ticket fares go up or down.
What is the cheapest month to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
January is typically the cheapest month to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.), with average return fares around AU$359. January often sees lower prices because it falls after the holiday travel rush, when demand tends to decrease. Other cheap months to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) include February and September.
Which airlines fly direct from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Only one airline offers direct flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.). Southwest Airlines operates 48 direct flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) every week.
What is the cheapest airline that flies from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering nonstop return flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.), with prices starting from around AU$105 for flights that can be booked for departure within the next year. Southwest Airlines offers one of the cheapest connecting return flights on this route, with a layover in Dallas (DAL-Love Field), starting from around AU$200. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) will differ from traveler to traveler. If you like to fly early, Southwest Airlines offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. Southwest Airlines offers the most daily flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) are typically January and September, with average return flights around AU$359. These months can be a great time to travel as they often fall outside peak holiday periods, giving you a good balance of affordable fares and potentially fewer crowds.
How many flights per day from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll find approximately 7 nonstop flights per day from Denver International Airport (DEN) to Midway International Airport (MDW). For even more choices, look at flights that include layovers, as there are around 163 connecting flights per day. Some common connection points include Love Field (DAL), Baltimore Washington International Thurgood Marshall (BWI), and Sky Harbor International (PHX).
What is the earliest flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Denver International Airport (DEN) to Midway International Airport (MDW) typically departs around 12:00 AM local time, operated by Frontier Airlines. This is a seasonal service, active in September and October. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Denver International Airport (DEN) to Chicago Midway International Airport (MDW) on a Friday, with around 84 flights available. This gives you plenty of options for your travel plans. Friday sees notably more flight options compared to other days of the week. Major airlines on this route include Southwest Airlines, Delta, and United.
What are the most popular departure times for flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Denver Intl. (DEN) to Midway Intl. (MDW) are in the morning, from 9am to 12pm. Many major carriers, including Southwest Airlines, Delta and Frontier Airlines, offer flights during this window. Many travellers prefer these times as it allows for an early start to their day at their destination.
How long does it take to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
A non-stop flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) typically takes around 2 hours 30 minutes. This route covers a distance of approximately 1439 kilometres. If you opt for a flight with one stop, your travel time will be significantly longer, usually around 8 hours. Flights with two or more stops generally take about 11 hours. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.
Can you fly business or first class from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Yes, you can fly business class or first class between DEN and MDW. You can fly business class with Frontier Airlines and Delta.First class cabins are available on Delta.
How do I earn miles on a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Denver, CO (DEN)?
If you're planning to travel to Chicago from Denver Intl. (DEN), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Love Field (DAL), Baltimore Washington Intl. Thurgood Marshall (BWI), or Sky Harbor Intl. (PHX) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Denver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
AU$284
Distance
1430 km
Average flight time
3 hours 23 mins

Book with confidence

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$284 to AU$390, 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.

Your quick guide to flights from Denver to Chicago

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*Available to Expedia members.