Question 1

How much does a flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) cost?

Accepted Answer

You can find cheap one-way flights from $75 and cheap return flights from $140 Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $114 and $470, and return flights often range between $246 and $742. 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 (MDW-Midway 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.

Question 2

What is the cheapest month to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

January is the cheapest month to fly from Denver to Chicago, with average round-trip fares around $240. This price is about 16% lower than the average throughout the year, as demand is typically lower after the holiday season. Other budget-friendly months include February and September.

*Averages based on flights available on Expedia in the last year.

Question 3

Which airlines fly direct from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

Enter DEN to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Question 4

What is the cheapest airline that flies from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

Frontier Airlines is one of the cheapest airlines offering nonstop flights from Denver (DEN) to Chicago (MDW), with round-trip tickets starting from around $400. 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.

Question 5

How do I find cheap flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

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.

Question 6

What is the best airline to fly with from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

The best airline to fly with from Denver, CO (DEN) to Chicago, IL (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. WN offers the most daily flights from Denver to Chicago, 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.

Question 7

What is the best time to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

For your trip from Denver (DEN) to Chicago (MDW), January and September are the best months to fly, with average return flight prices around $240. These months typically see lower demand, which translates to better prices and a more relaxed travel experience.

*Prices based on flights available on Expedia in the last year.

Question 8

How many flights per day from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

On average, there are around 6 nonstop flights per day from Denver Intl. (DEN) to Midway Intl. (MDW). For more options, look at flights that include layovers.

Question 9

What is the earliest flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

The earliest flight from Denver (DEN) to Chicago (MDW) usually departs at 12:00 AM, operated by Frontier Airlines. This is a seasonal service available in September and October, giving you a chance to maximize your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

Question 10

What are the most popular departure times for flights from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

The most popular departure times for flights from Denver, CO (DEN) to Chicago, IL (MDW) are in the early morning, from 6am to 9am. About 24% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Delta Air Lines, offer flights during this window. This timing is favored as it allows travelers to arrive in Chicago early and make the most of their day.

Question 11

How long does it take to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

Direct flights from DEN to MDW usually take about 2 hours 20 minutes, traveling roughly 894 miles. If you opt for a connecting flight, expect to add around 5 hours 40 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Question 12

Can you fly business or first class from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

First class seats are offered on the DEN to MDW route with Delta Air Lines.

Question 13

How do I earn miles on a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?

Accepted Answer

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.

Question 14

What airports do you fly into for Chicago from Denver Intl. (DEN)?

Accepted Answer

When traveling from Denver Intl. (DEN) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Portland Intl. (PDX), San Diego Intl. (SAN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Question 15

Is it cheaper to buy a plane ticket from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?

Accepted Answer

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.

Question 16

Is it cheaper to book a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?

Accepted Answer

Securing a Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway 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.

Question 17

Can I cancel or change the date of my flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?

Accepted Answer

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.

Origin airport	Denver Intl.
Destination airport	Midway Intl.
Airlines serving	Delta, Frontier Airlines, Southwest Airlines
Roundtrip price	$140
Distance	893 mi
Average flight time	3 hours 32 mins

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$75 Cheap Flights from Denver (DEN) to Chicago (MDW)