$99 Cheap Flights from Washington (DCA) to Chicago (MDW)

View $99 flight on Wed, Mar 18, 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 $99 for one-way flights and $195 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Apr 11 - Sat, Apr 18
DCA
Washington
MDW
Chicago
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Apr 11 from Washington to Chicago, returning Sat, Apr 18, priced at $195 found 3 days ago
Southwest Airlines
Tue, Mar 24 - Wed, Mar 25
DCA
Washington
MDW
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Mar 24 from Washington to Chicago, returning Wed, Mar 25, priced at $197 found 1 day ago
Southwest Airlines
Wed, Mar 25 - Tue, Mar 31
DCA
Washington
MDW
Chicago
$207 Roundtrip, found 5 hours ago
$207
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Mar 25 from Washington to Chicago, returning Tue, Mar 31, priced at $207 found 5 hours ago
Southwest Airlines
Tue, Mar 24 - Tue, Apr 7
DCA
Washington
MDW
Chicago
$212 Roundtrip, found 21 hours ago
$212
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Tue, Mar 24 from Washington to Chicago, returning Tue, Apr 7, priced at $212 found 21 hours ago
Southwest Airlines
Sat, Apr 11 - Sat, Apr 18
DCA
Washington
MDW
Chicago
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Apr 11 from Washington to Chicago, returning Sat, Apr 18, priced at $213 found 3 days ago
Southwest Airlines
Wed, Mar 25 - Tue, Mar 31
DCA
Washington
MDW
Chicago
$214 Roundtrip, found 5 hours ago
$214
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Mar 25 from Washington to Chicago, returning Tue, Mar 31, priced at $214 found 5 hours ago
Delta
Tue, Apr 28 - Tue, May 5
DCA
Washington
MDW
Chicago
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Apr 28 from Washington to Chicago, returning Tue, May 5, priced at $217 found 2 hours ago
Southwest Airlines
Sat, Mar 14 - Tue, Mar 17
DCA
Washington
MDW
Chicago
$221 Roundtrip, just found
$221
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Mar 14 from Washington to Chicago, returning Tue, Mar 17, priced at $221 just found
Southwest Airlines
Tue, Mar 24 - Tue, Apr 7
DCA
Washington
MDW
Chicago
$222 Roundtrip, found 21 hours ago
$222
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Tue, Mar 24 from Washington to Chicago, returning Tue, Apr 7, priced at $222 found 21 hours ago
Southwest Airlines
Wed, Jun 17 - Sat, Jun 20
DCA
Washington
MDW
Chicago
$223 Roundtrip, found 3 days ago
$223
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jun 17 from Washington to Chicago, returning Sat, Jun 20, priced at $223 found 3 days ago

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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 $246
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $246

Find the cheapest month to fly from Washington (DCA) to Chicago (MDW)

August is typically the cheapest month to fly

From $116 - $395 per traveler.

Frequently asked questions

How much does a flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $99 or cheap return flight from $195 from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
The cheapest month to fly from DCA to MDW is April, when there's less demand. Off-peak months are generally when airlines offer better prices between these airports.
Which airlines fly direct from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
When jetting out of Ronald Reagan Washington National Airport (DCA), you can get on a nonstop flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest DCA to MDW flight.
How many flights per day from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
With, on average, 5 direct flights that operate from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) each day, you'll be soaring through the skies in no time.
What are the most popular departure times for flights from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
More passengers fly between DCA and MDW at 6 AM than at any other point in the day. Looking for a quieter experience? Pick a flight outside the busiest times and it's possible you'll save on your ticket as well.
What day of the week has the most flights from DCA to MDW?
If you jet off on a Friday, you'll get the greatest range of choices for flights from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW).
What is the earliest flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
Ronald Reagan Washington National Airport (DCA)'s earliest flight to Midway Intl. Airport (MDW) leaves at approximately 6:05AM UTC-5. With a travel duration of 2h 10m, you'll land at around 7:15AM UTC-6.
How long does it take to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
The average flight time from DCA to MDW is 2 hours and 8 minutes, covering a total distance of 600 mi.
What is the best time to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
Opt for a flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Ronald Reagan Washington National Airport (DCA)?
Catch a direct flight from Ronald Reagan Washington National Airport (DCA) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another gateway to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your trip to book a flight from DCA to MDW often results in higher prices. While you may find some last-minute discounts, they're not always guaranteed. Be flexible with your itinerary to maximize your chances of getting a bargain.
Is it cheaper to book a DCA to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a DCA to MDW flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one place will take the hassle out of travel planning. Just secure your flights and select from our extensive range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)?
You can usually reschedule or cancel your DCA to MDW flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Ronald Reagan Washington National
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$195
Distance
598 mi
Average flight time
1 hour 12 mins

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 April. 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 $99 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.

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