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$91 Cheap Flights from Washington (DCA) to Chicago (MDW)

View $91 flight on Wed, Sep 9, 2026Opens in a new window

Popular airlines from Ronald Reagan Washington National Airport (DCA) to Chicago Midway Airport (MDW)

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Cheap Flights from Washington to Chicago (DCA-MDW)

Prices were available within the past 7 days and start at $91 for one-way flights and $181 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Aug 20 - Mon, Aug 24
DCA
Washington
MDW
Chicago
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Aug 20 from Washington to Chicago, returning Mon, Aug 24, priced at $181 just found
Southwest Airlines
Tue, Oct 13 - Thu, Oct 15
DCA
Washington
MDW
Chicago
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Oct 13 from Washington to Chicago, returning Thu, Oct 15, priced at $184 found 1 hour ago
Southwest Airlines
Thu, Aug 20 - Sat, Aug 22
DCA
Washington
MDW
Chicago
$186 Roundtrip, just found
$186
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Aug 20 from Washington to Chicago, returning Sat, Aug 22, priced at $186 just found
Southwest Airlines
Sat, Aug 22 - Tue, Aug 25
DCA
Washington
MDW
Chicago
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Washington to Chicago, returning Tue, Aug 25, priced at $187 found 5 days ago
Southwest Airlines
Sat, Oct 10 - Tue, Oct 13
DCA
Washington
MDW
Chicago
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 10 from Washington to Chicago, returning Tue, Oct 13, priced at $188 just found
Southwest Airlines
Sat, Oct 24 - Mon, Oct 26
DCA
Washington
MDW
Chicago
$191 Roundtrip, found 2 hours ago
$191
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Oct 24 from Washington to Chicago, returning Mon, Oct 26, priced at $191 found 2 hours ago
Southwest Airlines
Wed, Aug 12 - Sat, Aug 15
DCA
Washington
MDW
Chicago
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 12 from Washington to Chicago, returning Sat, Aug 15, priced at $191 just found
Southwest Airlines
Wed, Jul 29 - Wed, Aug 5
DCA
Washington
MDW
Chicago
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Jul 29 from Washington to Chicago, returning Wed, Aug 5, priced at $192 found 6 days ago
Southwest Airlines
Thu, Aug 20 - Mon, Aug 24
DCA
Washington
MDW
Chicago
$193 Roundtrip, just found
$193
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Aug 20 from Washington to Chicago, returning Mon, Aug 24, priced at $193 just found
Delta
Tue, Aug 11 - Sat, Aug 22
DCA
Washington
MDW
Chicago
$201 Roundtrip, found 5 hours ago
$201
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Aug 11 from Washington to Chicago, returning Sat, Aug 22, priced at $201 found 5 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $219
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $219

What you need to know for your flight from Ronald Reagan Washington National to Midway Intl.

Washington (DCA) to Chicago (MDW) at a glance

Travel between Washington (DCA) and Chicago (MDW) with a range of airlines offering flights on this popular domestic short-haul route. Whether you prefer full-service or budget-friendly options, you can easily compare choices to find an itinerary that aligns with your budget and schedule while you explore the iconic sights and neighborhoods of Chicago. Here, you'll find essential information for flights from Ronald Reagan Washington National Airport (DCA) to Midway International Airport (MDW).

  • Fastest flight duration: around 2 hours non-stop
  • Route distance: roughly 600 miles (970 km)
  • Flights per week: around 20+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $80–$385, depending on seasonality and how far ahead you book

Flights from Ronald Reagan Washington National Airport (DCA) to Midway International Airport (MDW)

Based on recent traveler bookings, here are the top airlines favored for flights from Washington to Chicago, particularly for non-stop and one-stop options. Popular layover choices include Detroit Metropolitan Wayne County Airport (DTW, approximately 55-minute layover), Denver International Airport (DEN, about 45 minutes), and John Glenn Columbus International Airport (CMH, roughly 2 hours and 45 minutes). These routes offer you the flexibility to explore various combinations of price, total travel time, and cabin class to create the ideal travel itinerary.

  • Southwest Airlines: This budget-friendly carrier provides both non-stop and one-stop flights, with one-way ticket prices usually falling between $80 and $385. It dominates the route, accounting for about 96% of departures, and non-stop flights typically take around 2 hours.
  • Delta: As a full-service airline, Delta offers one-stop flights, with one-way fares generally ranging from $100 to $335. It represents about 2% of departures on this route, featuring an in-flight duration of 3 hours and 15 minutes, leading to a total travel time of approximately 5 hours when including a layover.
  • Frontier Airlines: This low-cost airline provides one-stop services, with one-way fares commonly between $80 and $180. It accounts for roughly 2% of departures on the route, offering an in-flight time of 3 hours and 15 minutes, resulting in a total journey time of about 5 hours, factoring in a layover.

Best time to fly from Washington (DCA) to Chicago (MDW)

The most popular months for travelers flying from Washington to Chicago are March, April, and August, when peak temperatures in Chicago reach up to 73°F in August. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 25.7°F. For better deals, August usually offers the lowest average one-way fare around $158. Flight availability peaks in August, with approximately 26 flights per week, making it easier to find convenient departure times.

  • Cheapest time to fly: August usually offers good deals with average one-way fare around $158, roughly 21% cheaper than the yearly average.
  • Another budget-friendly time to fly: September typically offers an average one-way fare of around $168.
  • Most flight options: August has the highest number of flights from Washington to Chicago, with approximately 26 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January25.7°F (-3.5°C)Low10$215
February27.0°F (-2.8°C)Low13$220
March37.0°F (2.8°C)High17$228
April46.0°F (7.8°C)High20$211
May57.0°F (13.9°C)Average22$185
June67.3°F (19.6°C)Average23$193
July73.4°F (23.0°C)Average22$204
August73.0°F (22.8°C)High26$158
September67.1°F (19.5°C)Average21$168
October54.9°F (12.7°C)Average21$196
November42.3°F (5.7°C)Average21$201
December33.1°F (0.6°C)Low18$224

*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 Washington (DCA) to Chicago (MDW)

  • Washington to Chicago (DCA-ORD): O'Hare International Airport (ORD) is approximately 16 miles from Midway International Airport (MDW). One-way economy prices on this route generally range from $80 to $350, influenced by the season and how far in advance you book. Travelers can choose between non-stop and one-stop flights. Major airlines operating on this route include American Airlines and United, and first-class service is also an option.
  • Washington to Chicago (IAD-MDW): Washington Dulles International Airport (IAD) is located around 23 miles from Ronald Reagan Washington National Airport (DCA). Economy fares for this journey typically range from $80 to $350, based on the season and booking timing. This route generally features one-stop flights, with common layover points at Hartsfield-Jackson Atlanta International Airport (ATL) and Detroit Metropolitan Wayne County Airport (DTW). Leading airlines for this route include Frontier Airlines (a budget carrier) and Delta, with first-class seating available as well.
  • Washington to Chicago (IAD-ORD): Washington Dulles International Airport (IAD) is situated about 23 miles from Ronald Reagan Washington National Airport (DCA), while O'Hare International Airport (ORD) is roughly 16 miles from Midway International Airport (MDW). One-way economy fares on this route usually range from $85 to $385, depending on the season and advance booking. Travelers can select from both non-stop and one-stop options. United and Frontier Airlines (a low-cost carrier) are popular choices on this route, and first-class service is also offered.

How to find the best prices for flights from Washington (DCA) 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:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Evening departures, from 6 PM to 12 AM, often offer lower prices, while morning flights from 5 AM to 12 PM are the most popular. Additionally, flying on Monday generally provides cheaper rates, while Friday is the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. 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.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. 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 Ronald Reagan Washington National Airport

Chicago welcomes travelers from Washington with a range of transport options based on price, convenience, and proximity. For departures, Ronald Reagan Washington National Airport is roughly a 10-minute drive (covering about 5 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 find several key transport options nearby. Midway Station, a metro station, is located about 0.2 miles from the airport and is easily reachable on foot, while Chicago Ashburn Station, a train station, is approximately 4.1 miles away by car. For those looking to access maritime transport, Lyons Seaport, a seaport, is situated about 7.2 miles away by car.

Frequently asked questions

How much does a flight from Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $91 and cheap return flights from $181 Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $143 and $468, and return flights often range between $287 and $759. 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 (DCA-Ronald Reagan Washington National) 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
September is the cheapest month to fly from Washington, DC (DCA) to Chicago, IL (MDW), with average round-trip fares around $273. This is about 20% lower than the average price throughout the year, as travel demand tends to decrease after the summer peak. Other economical months include February and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
Enter DCA 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering connecting flights from Ronald Reagan Washington National (DCA) to Midway Intl. (MDW), with round-trip tickets starting from around $205.45. 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Washington, DC (DCA-Ronald Reagan Washington National) 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 Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Washington, DC (DCA) to Chicago (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, WN typically offers the lowest fares. WN offers the most daily flights from DCA to MDW, 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 Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly from Washington, DC (DCA) to Chicago, IL (MDW) is typically in September or February. During these months, you can find return flights at around $273, making them the cheapest options. September is a great time to visit Chicago as the summer crowds have thinned, while February offers lower prices after the holiday rush.*Prices based on flights available on Expedia in the last year.
How many flights per day from Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 6 nonstop flights per day from Ronald Reagan Washington National (DCA) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Washington, DC (DCA) to Chicago, IL (MDW) usually departs at around 6:00 AM, operated by Delta. This flight can help you maximize your time in Chicago, allowing you to arrive early in the day. 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW) are in the early morning, from 6am to 9am. About 31% of passengers prefer this time window. Many major carriers, including Southwest Airlines, Delta and Southwest Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with a full day ahead of you.
How long does it take to fly from Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
Direct flights from DCA to MDW usually take about 2 hours, traveling roughly 599 miles. If you opt for a connecting flight, expect to add around 3 hours 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 Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the DCA to MDW route with Delta Air Lines.
How do I earn miles on a Washington, DC (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Washington, DC (DCA-Ronald Reagan Washington National) 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 Ronald Reagan Washington National (DCA)?
When traveling from Ronald Reagan Washington National (DCA) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Nashville Intl. (BNA), Hartsfield-Jackson Atlanta Intl. (ATL), Orlando Intl. (MCO) 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Washington, DC (DCA-Ronald Reagan Washington National) 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Washington, DC (DCA-Ronald Reagan Washington National) 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 (DCA-Ronald Reagan Washington National) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Washington, DC (DCA-Ronald Reagan Washington National) 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

0
Origin airport
Ronald Reagan Washington National
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$181
Distance
598 mi

Book with confidence

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 August. 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 $91 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.

 

Washington to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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