$102 Cheap Flights from Denver (DEN) to Chicago (MDW)
Popular airlines from Denver Intl. Airport (DEN) to Chicago Midway Airport (MDW)
Frontier AirlinesFrontier Airlines
Southwest AirlinesSouthwest Airlines
DeltaDelta
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Cheap Flights from Denver to Chicago (DEN-MDW)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Denver (DEN) to Chicago (MDW) at a glance
Travel from Denver (DEN) to Chicago (MDW) with a selection of airlines on this domestic short-haul route. Explore your options between full-service and low-cost carriers to discover the best deals for your travel needs, whether you're seeking the cheapest flights from Denver or affordable flights that fit your schedule. Get ready to experience the iconic sights and neighborhoods of Chicago as you review key details for your journey from Denver International Airport to Midway International Airport.
- Fastest flight duration: around 2h 15m non-stop
- Route distance: roughly 900 miles (1,450 km)
- Flights per week: around 25+ flights with multiple daily departures on average
- Typical fares (one-way): economy tickets often range from $50–$330, depending on seasonality and how far ahead you book
Flights from Denver International Airport (DEN) to Midway International Airport (MDW)
According to recent traveler bookings, the top airlines flying from Denver to Chicago are favored for their non-stop and one-stop options. Popular layover spots include Minneapolis-St. Paul International Airport (MSP) with a layover of about 1 hour and 30 minutes, Detroit Metropolitan Wayne County Airport (DTW) also around 1 hour and 30 minutes, and Lambert-St. Louis International Airport (STL) with a shorter 40-minute layover. These choices allow travelers to mix and match factors like price, total travel time, and cabin class to create the ideal itinerary.
- Southwest Airlines: This budget-friendly airline provides both non-stop and one-stop flights, with one-way prices generally between $75 and $345. Southwest operates roughly 82% of the departures on this route, offering a typical non-stop travel duration of about 2 hours and 15 minutes.
- Frontier Airlines: As a low-cost option, Frontier offers non-stop and one-stop services, with one-way fares typically ranging from $50 to $215. Frontier accounts for around 16% of departures on this route, with a standard non-stop flight time of 2 hours and 15 minutes.
- Delta: This full-service airline provides one-stop service, with one-way pricing usually falling between $100 and $415. Delta represents about 1% of the departures on this route, featuring an in-flight duration of 4 hours and 30 minutes, culminating in a total travel time of approximately 6 hours and 15 minutes, including layover.
Best time to fly from Denver (DEN) to Chicago (MDW)
The most popular months for travelers flying from Denver to Chicago are June, July, and August, when peak temperatures in Chicago reach up to 73.4°F in July. If you prefer quieter travel, consider May, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 57°F. For better deals, October usually offers the lowest average one-way fare around $135. Flight availability peaks in July, with approximately 42 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 14 flights per week.
- Cheapest time to fly: October usually offers good deals with average one-way fare around $135, roughly 9% cheaper than the yearly average.
- More budget-friendly months to fly: May, June, and August typically offer average one-way fares of around $137.
- Most flight options: July has the highest number of flights from Denver to Chicago, with approximately 42 flights per week, giving you more flexibility in scheduling your trip.
| Month | Temperature | Demand | Weekly Flights | Average one-way Fare |
| January | 25.7°F (-3.5°C) | Average | 17 | $155 |
| February | 27.0°F (-2.8°C) | Moderately Low | 14 | $154 |
| March | 37.0°F (2.8°C) | Average | 20 | $163 |
| April | 46.0°F (7.8°C) | Average | 22 | $157 |
| May | 57.0°F (13.9°C) | Moderately Low | 23 | $136 |
| June | 67.3°F (19.6°C) | Moderately High | 34 | $138 |
| July | 73.4°F (23.0°C) | Moderately High | 42 | $145 |
| August | 73.0°F (22.8°C) | Moderately High | 33 | $138 |
| September | 67.1°F (19.5°C) | Average | 32 | $142 |
| October | 54.9°F (12.7°C) | Average | 30 | $135 |
| November | 42.3°F (5.7°C) | Average | 28 | $155 |
| December | 33.1°F (0.6°C) | Moderately Low | 30 | $168 |
*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.
Alternative routes from Denver (DEN) to Chicago (MDW)
- Denver to Chicago (DEN-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices on this route generally fall between $55 and $330, influenced by the time of year and how far in advance bookings are made. Travelers can choose from both non-stop and one-stop flights. Major airlines that operate on this route include American Airlines and United, with first-class service available as well.
- Colorado Springs to Chicago (COS-ORD): Colorado Springs Airport (COS) lies about 73 miles from Denver International Airport (DEN), while O'Hare International Airport (ORD) is roughly 16 miles from Midway International Airport (MDW). Economy fares for one-way flights on this route usually range from $100 to $460, varying by season and booking time. Both non-stop and one-stop flight options are typically offered. Leading airlines servicing this route are United and American Airlines, with first-class service options available.
- Colorado Springs to Chicago (COS-MDW): Colorado Springs Airport (COS) is situated around 73 miles from Denver International Airport (DEN). On this route, one-way economy fares typically range from $110 to $485, depending on the season and when you book. Passengers have access to both non-stop and one-stop flights. Major carriers for this route include Southwest Airlines, a low-cost option, alongside Delta.
How to find the best prices for flights from Denver (DEN) to Chicago (MDW)
Getting some of the best deals on flights from Denver to Chicago is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, which aligns with when most travelers make their reservations. Evening departures between 6 PM and midnight tend to be less expensive, while morning flights from 5 AM to noon are the most popular. Additionally, flying on Tuesday generally offers lower prices, even though Friday is the busiest travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at Midway International Airport from Denver International Airport
Chicago welcomes travelers from Denver with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
- Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
- Public transportation: From Midway International Airport, travelers can find several key transport links nearby. Midway Station, a metro station, is located about 0.2 miles from the airport and can be reached on foot, while Chicago Ashburn Station, a train station, is approximately 4.1 miles away by car. Additionally, Lyons Seaport, a seaport, is about 7.2 miles from the airport, also accessible by car.
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 November. 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 $102 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, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $102 and cheap return flights $171 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.
What is the cheapest month to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
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.
Which airlines fly direct from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter DEN to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
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 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.
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) 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.
What is the best time to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
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.
How many flights per day from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
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.
What is the earliest flight from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
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.
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, 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.
How long does it take to fly from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
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.
Can you fly business or first class from Denver, CO (DEN-Denver Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the DEN to MDW route with Delta Air Lines.
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 from Denver Intl. (DEN)?
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.
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.) 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 (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. Airport |
|---|---|
Destination airport | Chicago Midway Airport |
Distance | 893 miles away |
Airlines serving | Frontier Airlines, Southwest Airlines, Delta |
Popular airline | Frontier Airlines |
Roundtrip price | $171 |
Average flight time | 3 hours 29 mins |