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$83+ Cheap flights from District of Columbia to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from District of Columbia to Midway

Keep the following information in mind while searching for District of Columbia to Midway flight deals. Data was last updated July 31, 2025.

Round-trip from

$174
(Mytrip)

One-way from

$83
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$266

Good round-trip deal

$220 or less

Good one-way deal

$155 or less
From District of Columbia to Chicago Midway
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One-way flight from District of Columbia to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from District of Columbia to Chicago Midway.
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Price to beat on a one-way flight from District of Columbia to Chicago Midway.
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Find flight deals from District of Columbia to Midway

Cheapest flights from District of Columbia to Midway
Explore the most affordable flight options available from District of Columbia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:22 pmIAD - MDW
1 stop5h 55mAllegiant Air
Fri 8/229:32 amMDW - IAD
1 stop4h 51mAllegiant Air
Deal found 7/29$174
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:14 pmIAD - MDW
1 stop15h 04mFrontier
Sat 9/2010:51 amMDW - IAD
1 stop6h 33mFrontier
Deal found 7/30$177
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:25 amDCA - MDW
Nonstop2h 00mSouthwest
Sat 9/612:45 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 7/31$217
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:25 pmIAD - MDW
1 stop4h 47mDelta
Tue 9/29:30 amMDW - IAD
1 stop12h 56mDelta
Deal found 7/29$227
This Mytrip deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:00 pmDCA - MDW
1 stop8h 54mFrontier
Mon 8/1812:35 pmMDW - DCA
1 stop27h 24mFrontier
Deal found 7/29$228
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amDCA - MDW
1 stop3h 35mDelta
Sat 8/304:25 pmMDW - DCA
1 stop5h 21mDelta
Deal found 7/31$237

Cheapflights Fare Finder

 
Customize your flight search to find flights from District of Columbia to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from District of Columbia to Chicago Midway Airport that are best for you.

Fly from

District of Columbia

Fly to

Midway

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/13

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/20

10:51 am-6:24 pm

1 stop6h 33m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

12:45 pm-3:40 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/30

5:25 pm-9:12 pm

1 stop4h 47m

Chicago Midway

Tue 9/2

9:30 am-11:26 pm

1 stop12h 56m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/16

1:00 pm-8:54 pm

1 stop8h 54m

Chicago Midway

Mon 8/18

12:35 pm-4:59 pm

1 stop27h 24m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 8/27

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 8/30

4:25 pm-10:46 pm

1 stop5h 21m

$237

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/5

6:10 am-10:40 am

1 stop5h 30m

$83

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 8/26

11:55 am-12:50 pm

Nonstop1h 55m

$109

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 10/11

6:00 pm-10:38 pm

1 stop29h 38m

$116

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/26

5:25 pm-9:44 pm

1 stop5h 19m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 results
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Best time to book a flight from District of Columbia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from District of Columbia with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from District of Columbia to Chicago Midway Airport

What is the cheapest month to book a flight from District of Columbia to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $160). Flying from District of Columbia to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DC to MDW?

Find hourly flight availability from District of Columbia to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from District of Columbia to Chicago Midway Airport as you normally would.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from District of Columbia to Chicago Midway Airport, such as Southwest, Delta, and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from District of Columbia to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from District of Columbia to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from District of Columbia to Chicago Midway Airport are Frontier ($83), Southwest ($109), and Delta ($119).

  • What are the most reliable airlines from District of Columbia to Chicago Midway Airport?

    Consider United Airlines (100%), Southwest (71%) or Frontier (52%) when booking your flight. These represent the most reliable airlines when flying from District of Columbia to Chicago Midway Airport.

  • What are the cheapest flights from District of Columbia to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $67. While the most popular route (Washington, D.C. Dulles Intl - Chicago Midway) can be booked for $178 on average our data indicates $174 when flying from District of Columbia to Chicago Midway Airport.

  • Can I find deals for flights from District of Columbia to Midway that include hotel bookings?

    Yes. In addition to deals on District of Columbia to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from District of Columbia to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from District of Columbia to Midway.

  • Can I find deals for business class flights from District of Columbia to Midway?

    Yes. Cheapflights offers flight deals from District of Columbia to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from District of Columbia to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from District of Columbia to Chicago Midway Airport (average of $160). Flying from District of Columbia to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for District of Columbia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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San Francisco to Midway flights
Tampa to O'Hare Intl flights
Boston to Midway flights
Las Vegas to O'Hare Intl flights
Love Field to Midway flights
Reagan-National to Midway flights

Top 4 airlines flying from District of Columbia to Midway

Discover the top 4 airlines that operate flights from District of Columbia to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$193FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$328FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$351FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$161Average$297FlexibilityNo cancel feeOn-time63%

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