$44 Cheap Flights from Denver (DEN) to Chicago (ORD)

View $44 flight on Tue, Jun 2, 2026Opens 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 $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Sep 9 - Wed, Sep 23
DEN
Denver
ORD
Chicago
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Denver to Chicago, returning Wed, Sep 23, priced at $88 found 1 hour ago
Frontier Airlines
Sat, Sep 12 - Tue, Sep 15
DEN
Denver
ORD
Chicago
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 12 from Denver to Chicago, returning Tue, Sep 15, priced at $90 just found
Frontier Airlines
Thu, Sep 10 - Sat, Sep 19
DEN
Denver
ORD
Chicago
$92 Roundtrip, found 1 hour ago
$92
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Denver to Chicago, returning Sat, Sep 19, priced at $92 found 1 hour ago
Frontier Airlines
Thu, Sep 10 - Wed, Sep 16
DEN
Denver
ORD
Chicago
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 10 from Denver to Chicago, returning Wed, Sep 16, priced at $100 just found
Frontier Airlines
Sat, Oct 3 - Mon, Oct 5
DEN
Denver
ORD
Chicago
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 3 from Denver to Chicago, returning Mon, Oct 5, priced at $102 found 3 hours ago
Frontier Airlines
Tue, Sep 1 - Sat, Sep 5
DEN
Denver
ORD
Chicago
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Denver to Chicago, returning Sat, Sep 5, priced at $108 found 8 hours ago
American Airlines
Wed, Aug 19 - Wed, Aug 26
DEN
Denver
ORD
Chicago
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 19 from Denver to Chicago, returning Wed, Aug 26, priced at $217 found 1 hour ago
United
Wed, Aug 19 - Wed, Aug 26
DEN
Denver
ORD
Chicago
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Aug 19 from Denver to Chicago, returning Wed, Aug 26, priced at $217 found 1 hour ago
Southwest Airlines
Tue, Jun 2 - Wed, Jun 3
DEN
Denver
ORD
Chicago
$217 Roundtrip, found 5 hours ago
$217
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jun 2 from Denver to Chicago, returning Wed, Jun 3, priced at $217 found 5 hours ago
Delta
Wed, Aug 19 - Wed, Aug 26
DEN
Denver
ORD
Chicago
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Aug 19 from Denver to Chicago, returning Wed, Aug 26, priced at $237 found 1 hour ago

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. Closest option available. Average driving time to city center is 16 minutes. Flights from $357
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $357

Frequently asked questions

How much does a flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $44 and cheap return flights from $88 Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $110 and $984, and return flights often range between $237 and $1102. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is the cheapest month to fly from Denver, CO (DEN) to Chicago, IL (ORD), with average round-trip fares around $216. This price is about 17% lower than the average throughout the year, as demand typically decreases after the summer travel season. Other budget-friendly months to consider are May and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Choose from 4 airlines operating direct flights from DEN to ORD:

  • United operates around 84 direct flights from DEN to ORD every week
  • American Airlines operates around 43 direct flights from DEN to ORD every week
  • Frontier Airlines operates around 8 direct flights from DEN to ORD every week
  • British Airways operates around 7 direct flights from DEN to ORD every week

What is the cheapest airline that flies from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Sun Country Airlines is one of the cheapest airlines offering connecting flights from Denver (DEN) to Chicago (ORD), with round-trip tickets starting from around $328. 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.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.)?
The best airline to fly with from Denver, CO (DEN) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. United offers the most daily flights from DEN to ORD, 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 (ORD-O'Hare Intl.)?
The best times to fly from Denver, CO (DEN) to Chicago, IL (ORD) are in September and August. September offers average return flight prices around $216, making it a budget-friendly option, while August is also popular. These months provide a great combination of affordability and favorable travel conditions.*Prices based on flights available on Expedia in the last year.
How many flights per day from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can find approximately 19 nonstop flights per day from Denver Intl. (DEN) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Denver, Colorado (Denver Intl.) to Chicago, Illinois (O'Hare Intl.) typically departs at around 12:00 AM. This seasonal service is available from June to November, giving you a chance to start your trip to Chicago early. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Denver (DEN) to Chicago (ORD) are in the early morning, from 6am to 9am. About 28% of passengers prefer this time window. Many major carriers, including United, American Airlines and Delta Airlines, offer flights during this window. This timing is favored because it allows you to maximize your time in Chicago upon arrival.
How long does it take to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from DEN to ORD takes around 2 hours 50 minutes, with the route covering approximately 886 miles. Flights with a layover typically take 5 hours 10 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between DEN and ORD. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United Airlines

How much is a business class flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Denver, CO (DEN) to Chicago, IL (ORD) typically costs between $947 - $1,478. A non-stop, one-way business class flight is usually around $450 - $865. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare 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 from Denver Intl. (DEN)?
When traveling from Denver Intl. (DEN) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Love Field (DAL), 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 (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare 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 (ORD-O'Hare Intl.) flight and hotel package?
Securing a Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages 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 (ORD-O'Hare Intl.)?
If you booked your Denver, CO (DEN-Denver Intl.) to Chicago, IL (ORD-O'Hare 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
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United
Roundtrip price
$88
Distance
886 mi
Average flight time
3 hours 36 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 September. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $44 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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