$69 Cheap Flights from Denver (DEN) to Chicago (MDW)

View $69 flight on Tue, Jun 3, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Denver to Chicago (DEN-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, May 27 - Sat, May 31
DEN
Denver
MDW
Chicago
$138 Roundtrip, found 11 hours ago
$138
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, May 27 from Denver to Chicago, returning Sat, May 31, priced at $138 found 11 hours ago
Frontier Airlines
Sat, May 31 - Tue, Jun 3
DEN
Denver
MDW
Chicago
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 31 from Denver to Chicago, returning Tue, Jun 3, priced at $144 found 2 days ago
Southwest Airlines
Wed, May 14 - Tue, May 27
DEN
Denver
MDW
Chicago
$151 Roundtrip, found 9 hours ago
$151
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, May 14 from Denver to Chicago, returning Tue, May 27, priced at $151 found 9 hours ago
Southwest Airlines
Wed, Jun 4 - Tue, Jun 10
DEN
Denver
MDW
Chicago
$151 Roundtrip, found 1 hour ago
$151
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Jun 4 from Denver to Chicago, returning Tue, Jun 10, priced at $151 found 1 hour ago
Frontier Airlines
Tue, Jun 3 - Mon, Jun 9
DEN
Denver
MDW
Chicago
$154 Roundtrip, found 1 hour ago
$154
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jun 3 from Denver to Chicago, returning Mon, Jun 9, priced at $154 found 1 hour ago
Southwest Airlines
Wed, May 14 - Tue, May 27
DEN
Denver
MDW
Chicago
$156 Roundtrip, found 9 hours ago
$156
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, May 14 from Denver to Chicago, returning Tue, May 27, priced at $156 found 9 hours ago
Southwest Airlines
Fri, May 30 - Tue, Jun 3
DEN
Denver
MDW
Chicago
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, May 30 from Denver to Chicago, returning Tue, Jun 3, priced at $159 found 1 day ago
Southwest Airlines
Wed, May 28 - Tue, Jun 3
DEN
Denver
MDW
Chicago
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 28 from Denver to Chicago, returning Tue, Jun 3, priced at $159 found 1 day ago
Southwest Airlines
Sat, Jul 5 - Tue, Jul 8
DEN
Denver
MDW
Chicago
$160 Roundtrip, just found
$160
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Jul 5 from Denver to Chicago, returning Tue, Jul 8, priced at $160 just found
Southwest Airlines
Wed, May 21 - Wed, May 28
DEN
Denver
MDW
Chicago
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, May 21 from Denver to Chicago, returning Wed, May 28, priced at $161 found 2 days ago
Flights from Denver (DEN) to Chicago (MDW)
Origin airport
Denver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$138
Distance
893 mi

Denver to Chicago Flights

The cheapest times to fly from Denver 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 Denver to Chicago are during the month of May. You can find some of the cheapest flights from Denver to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Denver to Chicago

Sunday is one of the best days to book for cheap flights from Denver 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 Denver 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 Denver to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 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 Denver 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 Denver 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.

Frequently asked questions

How much does a flight from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW) cost?
You’ll find affordable return tickets from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW) starting from $148. Grab a seat and get ready for takeoff. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Frontier Airlines flight leaving DEN on May 13 2025 and touching down at MDW. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from DEN to MDW?
The cheapest flights from DEN to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
Take a nonstop flight with Southwest Airlines and journey straight from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from DEN to MDW?
Take off from DEN to MDW with Southwest Airlines. This airline currently has the cheapest one-way fare for this route, starting from $76. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from DEN on June 11 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
Each day on average, 6 direct flights take off from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW). Pick the departure time that best fits your itinerary.
What are the most popular departure times for flights from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
More people fly between DEN and MDW at 8 PM than at any other point in the day. Looking for a quieter experience? Try choosing a quieter departure window and you’re likely to save on your ticket as well.
What day of the week has the most flights from DEN to MDW?
Monday has the most flights from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW). Consider jetting off on this day and you’ll have the best chance of finding a departure that fits your itinerary.
What is the earliest flight from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
Hop on the earliest flight at around 5:50AM UTC-7, departing from Denver Intl. Airport (DEN). You’ll be flying for roughly 2h 30m, touching down at Midway Intl. Airport (MDW) at approximately 9:20AM UTC-6.
How long does it take to fly from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
The average flight duration from DEN to MDW is 2 hours and 20 minutes, covering a distance of 890 mi.
What is the best time to fly from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
Select a flight from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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.
What airports do you fly into for Chicago from Denver Intl. Airport (DEN)?
If you’re departing on a direct flight from Denver Intl. Airport (DEN) to Chicago, you can land at either O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your trip to book a ticket from DEN to MDW generally means paying more. While it’s possible to find some last-minute discounts, they’re not always guaranteed. Keep your travel plans flexible to maximize your chances of landing a bargain.
Is it cheaper to book a DEN to MDW flight and hotel package?
You’ll generally save money by securing a DEN to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage everything in one convenient place. After choosing your preferred accommodations and flights, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Denver Intl. Airport (DEN) to Midway Intl. Airport (MDW)?
Typically, it’s possible to reschedule or cancel your DEN to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and if any costs are involved. You’ll also find more details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.