$81 Cheap Flights from Washington (DCA) to Chicago (MDW)

View $81 flight on Fri, Jul 4, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Washington to Chicago (DCA-MDW)

Prices were available within the past 7 days and start at $81 for one-way flights and $161 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, May 24 - Sun, May 25
DCA
Washington
MDW
Chicago
$161 Roundtrip, found 7 hours ago
$161
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from Washington to Chicago, returning Sun, May 25, priced at $161 found 7 hours ago
Southwest Airlines
Fri, Jul 4 - Sat, Jul 5
DCA
Washington
MDW
Chicago
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Washington to Chicago, returning Sat, Jul 5, priced at $167 found 5 days ago
Southwest Airlines
Sun, May 25 - Wed, May 28
DCA
Washington
MDW
Chicago
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, May 25 from Washington to Chicago, returning Wed, May 28, priced at $170 found 1 hour ago
Southwest Airlines
Fri, Jul 4 - Sat, Jul 5
DCA
Washington
MDW
Chicago
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Washington to Chicago, returning Sat, Jul 5, priced at $176 found 5 days ago
Delta
Tue, Jul 1 - Fri, Jul 4
DCA
Washington
MDW
Chicago
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jul 1 from Washington to Chicago, returning Fri, Jul 4, priced at $179 found 4 days ago
Southwest Airlines
Sun, May 25 - Wed, May 28
DCA
Washington
MDW
Chicago
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, May 25 from Washington to Chicago, returning Wed, May 28, priced at $180 found 1 hour ago
Frontier Airlines
Sat, May 24 - Thu, May 29
DCA
Washington
MDW
Chicago
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 24 from Washington to Chicago, returning Thu, May 29, priced at $184 found 2 days ago
Delta
Sun, May 25 - Wed, May 28
DCA
Washington
MDW
Chicago
$188 Roundtrip, found 1 hour ago
$188
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, May 25 from Washington to Chicago, returning Wed, May 28, priced at $188 found 1 hour ago
Delta
Fri, Jul 4 - Sat, Jul 5
DCA
Washington
MDW
Chicago
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 4 from Washington to Chicago, returning Sat, Jul 5, priced at $194 found 5 days ago
Southwest Airlines
Sun, May 25 - Thu, Jun 26
DCA
Washington
MDW
Chicago
$195 Roundtrip, found 1 hour ago
$195
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, May 25 from Washington to Chicago, returning Thu, Jun 26, priced at $195 found 1 hour ago

Frequently asked questions

How much does a flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) cost?
Score cheap return tickets from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) starting from $140. Book your seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving DCA on May 20 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from DCA to MDW?
The cheapest flights from DCA to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 DCA to MDW?
Travel from DCA to MDW with Southwest Airlines. This carrier currently offers the cheapest one-way fare for this route, starting from $81. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from DCA on July 4 2025. Prices were last updated on April 24 2025 and have not changed since.
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.
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