$29 Cheap Flights from Denver (DEN) to Chicago (ORD)

View $29 flight on Wed, Dec 31, 2025Opens in a new window

Popular airlines from Denver Intl. Airport (DEN) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Denver to Chicago (DEN-ORD)

Prices were available within the past 7 days and start at $29 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Jan 22 - Fri, Jan 23
DEN
Denver
ORD
Chicago
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Denver to Chicago, returning Fri, Jan 23, priced at $56 found 3 hours ago
Frontier Airlines
Wed, Nov 19 - Mon, Nov 24
DEN
Denver
ORD
Chicago
$59 Roundtrip, found 19 hours ago
$59
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Nov 19 from Denver to Chicago, returning Mon, Nov 24, priced at $59 found 19 hours ago
Frontier Airlines
Thu, Jan 22 - Fri, Jan 23
DEN
Denver
ORD
Chicago
$64 Roundtrip, found 3 hours ago
$64
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Denver to Chicago, returning Fri, Jan 23, priced at $64 found 3 hours ago
Frontier Airlines
Thu, Nov 27 - Mon, Dec 8
DEN
Denver
ORD
Chicago
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 27 from Denver to Chicago, returning Mon, Dec 8, priced at $68 found 2 days ago
Frontier Airlines
Sun, Dec 7 - Mon, Dec 8
DEN
Denver
ORD
Chicago
$69 Roundtrip, found 3 hours ago
$69
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Dec 7 from Denver to Chicago, returning Mon, Dec 8, priced at $69 found 3 hours ago
Frontier Airlines
Tue, Nov 11 - Wed, Nov 19
DEN
Denver
ORD
Chicago
$71 Roundtrip, found 13 hours ago
$71
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Nov 11 from Denver to Chicago, returning Wed, Nov 19, priced at $71 found 13 hours ago
Southwest Airlines
Wed, Feb 11 - Sat, Feb 14
DEN
Denver
ORD
Chicago
$166 Roundtrip, found 6 hours ago
$166
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Feb 11 from Denver to Chicago, returning Sat, Feb 14, priced at $166 found 6 hours ago
Sun Country Airlines
Tue, Dec 30 - Wed, Dec 31
DEN
Denver
ORD
Chicago
$213 Roundtrip, found 3 hours ago
$213
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Tue, Dec 30 from Denver to Chicago, returning Wed, Dec 31, priced at $213 found 3 hours ago
Alaska Airlines
Fri, Dec 5 - Sat, Dec 6
DEN
Denver
ORD
Chicago
$256 Roundtrip, found 3 hours ago
$256
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Fri, Dec 5 from Denver to Chicago, returning Sat, Dec 6, priced at $256 found 3 hours ago
JetBlue Airways
Wed, Dec 10 - Sat, Dec 13
DEN
Denver
ORD
Chicago
$329 Roundtrip, found 11 hours ago
$329
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Wed, Dec 10 from Denver to Chicago, returning Sat, Dec 13, priced at $329 found 11 hours ago

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

March is typically the cheapest month to fly

From $53 - $348 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $140
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $140

Frequently asked questions

How much does a flight from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $29 or cheap return flight from $56 from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD) 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 Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
January is the most affordable month to fly from DEN to ORD. Traveling outside of peak seasons is often the key to landing a great deal.
Which airlines fly direct from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
Skip the stopovers and fly nonstop to O'Hare Intl. Airport (ORD) from Denver Intl. Airport (DEN) with 4 carriers, including:

  • United Airlines
  • Southwest Airlines
  • American Airlines

What is the cheapest airline that flies from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Denver Intl. Airport (DEN) and O'Hare Intl. Airport (ORD) will vary based on your travel dates. Frontier Airlines and American Airlines are just some of the choices offering well-priced fares. Use Expedia's filter tool to compare airlines in one place and find the right DEN to ORD flight for your budget.
How many flights per day from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
When taking off from Denver Intl. Airport (DEN), you can choose from an average of 14 daily direct flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
The 5 PM departures from DEN to ORD are the most sought after. These flights can come with a higher price due to their popularity. If you're looking to save, choose a less crowded time to fly.
What day of the week has the most flights from DEN to ORD?
Jet off on a Sunday if you're looking for the best choice of flights from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
Take the earliest flight at around 6:00AM UTC-7, departing from Denver Intl. Airport (DEN). You'll be in the air for approximately 2h 38m, landing at O'Hare Intl. Airport (ORD) at approximately 9:38AM UTC-6.
How long does it take to fly from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
It usually takes 2 hours and 32 minutes to cover the 890 mi from DEN to ORD.
What is the best time to fly from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on schedule, opt for a flight that takes off from Denver Intl. Airport (DEN) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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)?
You'll touch down at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Denver Intl. Airport (DEN).
Is it cheaper to buy a plane ticket from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book your flight from DEN to ORD often results in higher prices. While you might find some last-minute discounts, there's no guarantee. Allow some flexibility in your schedule to boost your chances of scoring a bargain.
Is it cheaper to book a DEN to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a DEN to ORD flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the stress out of travel planning. Just pick your flights and select from our wide range of stays, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Denver Intl. Airport (DEN) to O'Hare Intl. Airport (ORD)?
Usually, it's possible to reschedule or cancel your DEN to ORD flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Denver Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United
Roundtrip price
$54
Distance
886 mi
Average flight time
3 hours 30 mins

Book with confidence

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 January. 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 $29 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.

 

Denver to Chicago Flights

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