$82 Cheap Flights from Washington (IAD) to Chicago (MDW)
Popular airlines from Washington Dulles Intl. Airport (IAD) to Chicago Midway Airport (MDW)
Frontier AirlinesFrontier Airlines
DeltaDelta
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Cheap Flights from Washington to Chicago (IAD-MDW)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Washington (IAD) to Chicago (MDW) at a glance
Discover a range of airlines offering flights from Washington Dulles International Airport (IAD) to Midway International Airport (MDW) on this domestic short-haul route to Chicago. You can compare options from both full-service and budget carriers to find the best itinerary that suits your travel plans, schedule, and budget. Stay updated with price alerts and daily fares as you prepare to explore Chicago's iconic sights and vibrant neighborhoods.
- Fastest flight duration: around 4 hours in-flight, plus roughly 1h 30m layover with one stop
- Route distance: roughly 600 miles (970 km)
- Flights per week: around 8 departures on average
- Typical fares (one-way): economy tickets often range from $80–$350, depending on seasonality and how far ahead you book
Flights from Washington Dulles International Airport (IAD) to Midway International Airport (MDW)
Based on the latest traveler bookings, here are the top airlines favored for flights from Washington to Chicago, primarily offering one-stop services. Popular layover options include Hartsfield-Jackson Atlanta International Airport (ATL) with an approximately 1 hour 30 minute layover, Detroit Metropolitan Wayne County Airport (DTW) with about a 50 minute layover, and Tampa International Airport (TPA) featuring roughly 1 hour 45 minutes of downtime. These choices allow you to adjust price, total travel time, and cabin class for the ideal itinerary.
- Frontier Airlines: This budget-friendly airline provides one-stop flights, with one-way tickets generally priced between $80 and $210. It represents around 59% of departures for this particular route, featuring an in-flight duration of 4 hours and an overall travel time of about 5 hours and 30 minutes, including the layover.
- Delta: As a full-service airline, Delta offers one-stop service with one-way fares typically ranging from $100 to $370. It comprises roughly 39% of departures on this route, with a flight time of 4 hours and a total journey length of approximately 5 hours and 30 minutes, factoring in the layover.
Alternative routes from Washington (IAD) to Chicago (MDW)
- Washington to Chicago (IAD-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy prices for this journey generally fall between $85 and $385, influenced by the time of year and how far in advance you book. Travelers can choose from both non-stop and one-stop flights on this route. Major airlines servicing this route include United and Frontier Airlines, a budget carrier. First-class service is also offered for this route.
- Washington to Chicago (DCA-ORD): Ronald Reagan Washington National Airport (DCA) lies about 23 miles from Washington Dulles International Airport (IAD), while O'Hare International Airport (ORD) is around 16 miles from Midway International Airport (MDW). One-way economy fares on this route typically range from $80 to $350, varying with the season and booking time. Non-stop and one-stop flights are commonly available. Key airlines operating on this route include American Airlines and United, with first-class service also available.
- Washington to Chicago (DCA-MDW): Ronald Reagan Washington National Airport (DCA) is situated roughly 23 miles from Washington Dulles International Airport (IAD). One-way economy ticket prices for this route usually range from $80 to $385, depending on the time of year and how early you book. This route offers both non-stop and one-stop flight options. Leading airlines on this route are Southwest Airlines, a low-cost carrier, and Delta. First-class service is also provided on this route.
How to find the best prices for flights from Washington (IAD) to Chicago (MDW)
Getting some of the best deals on flights from Washington 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 typically available when booking 2-8 weeks in advance, although most travelers tend to book within 2 weeks. Morning departures (5 am-12 pm) generally offer lower prices and are also the most popular flight times. Additionally, flying on Monday often results in cheaper rates, while Wednesday remains the most popular 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 Washington Dulles International Airport
Chicago welcomes travelers from Washington with a range of transport options based on price, convenience, and proximity. For departures, Washington Dulles International Airport is roughly a 40-minute drive (covering about 29 miles) from central Washington. 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 easily reach several transport links. Midway Station, a metro station, is located about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is approximately 4.1 miles away by car. Additionally, Lyons Seaport, a seaport, is situated about 7.2 miles from the airport, also accessible by car.
Washington to Chicago Flights
The cheapest times to fly from Washington 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 Washington to Chicago are during the month of November. You can find some of the cheapest flights from Washington to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Washington to Chicago
Sunday is one of the best days to book for cheap flights from Washington 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 Washington 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 Washington to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $82 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 Washington 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 Washington 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $82 and cheap return flights $161 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights usually range from $126 to $614, and return flights typically cost between $353 and $1268. 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 Washington, DC (IAD-Washington Dulles 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from IAD to MDW is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter IAD to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering connecting flights from Washington Dulles Intl. (IAD) to Midway Intl. (MDW), with round-trip tickets starting from around $154. 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Washington, DC (IAD-Washington Dulles 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 time to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago (MDW-Midway Intl.) typically departs at around 5:00 AM, operated by Southwest Airlines. This is a seasonal service active in June and July, allowing you to start your day early 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Washington, DC (IAD) to Chicago, IL (MDW) are in the morning, from 6am to 9am. About 45% of passengers prefer this time window. Many major carriers, including Delta Airlines and United Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with plenty of time to explore the city.
How long does it take to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from IAD to MDW with one stop typically take around 7 hours, covering approximately 576 miles. 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the IAD to MDW route with Delta Air Lines.
How do I earn miles on a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Washington, DC (IAD-Washington Dulles 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 Washington Dulles Intl. (IAD)?
When traveling from Washington Dulles Intl. (IAD) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), DuBois Regional (DUJ), LNS (LNS) 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Washington, DC (IAD-Washington Dulles 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Washington, DC (IAD-Washington Dulles 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Washington, DC (IAD-Washington Dulles 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 | Washington Dulles Intl. Airport |
|---|---|
Destination airport | Chicago Midway Airport |
Distance | 575 miles away |
Airlines serving | Frontier Airlines, Delta |
Popular airline | Frontier Airlines |
Roundtrip price | $161 |