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$85+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$181
(Frontier)

One-way from

$85
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$279

Good round-trip deal

$258 or less

Good one-way deal

$160 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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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. 6% potential increase in price ($18 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 April 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 April 30, 2025.

This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/153:32 pmIAD - MDW
1 stop9h 07mFrontier
Sat 5/1710:48 amMDW - IAD
1 stop4h 46mFrontier
Deal found 4/29$181
This Southwest deal was found by Cheapflights users on 4/28. 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 5/246:50 pmDCA - MDW
1 stop4h 00mSouthwest
Sun 5/259:20 amMDW - DCA
1 stop4h 40mSouthwest
Deal found 4/28$181
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/51:00 pmDCA - MDW
1 stop7h 08mFrontier
Thu 5/158:03 pmMDW - DCA
1 stop24h 56mFrontier
Deal found 4/27$191
This Delta deal was found by Cheapflights users on 4/29. 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 5/243:37 pmIAD - MDW
1 stop6h 36mDelta
Sun 5/256:00 amMDW - IAD
1 stop4h 41mDelta
Deal found 4/29$197
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 7/19:39 amDCA - MDW
1 stop3h 50mDelta
Thu 7/31:09 pmMDW - DCA
1 stop4h 50mDelta
Deal found 4/29$197
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Thu 6/193:58 pmIAD - MDW
1 stop16h 17mAllegiant Air
Sun 6/2211:45 amMDW - IAD
2 stops25h 38mAllegiant Air
Deal found 4/29$294
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Thu 6/53:58 pmIAD - MDW
1 stop16h 17mMultiple Airlines
Mon 6/98:05 amMDW - IAD
3 stops26h 21mMultiple Airlines
Deal found 4/29$314

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 April 30, 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

Thu 5/15

3:32 pm-11:39 pm

1 stop9h 07m

Chicago Midway

Sat 5/17

10:48 am-4:34 pm

1 stop4h 46m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/24

6:50 pm-9:50 pm

1 stop4h 00m

Chicago Midway

Sun 5/25

9:20 am-3:00 pm

1 stop4h 40m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 5/11

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/15

8:03 pm-4:59 pm

1 stop19h 56m

$191

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

3:37 pm-9:13 pm

1 stop6h 36m

Chicago Midway

Sun 5/25

6:00 am-11:41 am

1 stop4h 41m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 7/1

9:39 am-12:29 pm

1 stop3h 50m

Chicago Midway

Thu 7/3

1:09 pm-6:59 pm

1 stop4h 50m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/19

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Sun 6/22

11:45 am-2:23 pm

2 stops25h 38m

$294

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/5

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Mon 6/9

8:05 am-11:26 am

3 stops26h 21m

$314

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 7/19

6:10 am-10:35 pm

1 stop17h 25m

$85

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 7/4

3:00 pm-6:30 pm

1 stop4h 30m

$86

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/8

3:58 pm-7:15 am

1 stop16h 17m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 14 results
1
2

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 April 30, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 30, 2025.
To help decide which airline to fly from District of Columbia to Chicago, see what other customers have to say about 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
4,295 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 ($85), Southwest ($86), and Allegiant Air ($90).

  • 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 District of Columbia?

Book flights to District of Columbia if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$197FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$304FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$351FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$177Average$307FlexibilityNo cancel feeOn-time63%

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