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$81+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$159
(Mytrip)

One-way from

$81
(Frontier)

Popular in

March

Cheapest in

September

Average price

$244

Good round-trip deal

$229 or less

Good one-way deal

$176 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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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 3/610:25 pmIAD - MDW
1 stop24h 00mFrontier
Mon 3/104:20 pmMDW - IAD
1 stop19h 56mFrontier
Deal found 2/20$159
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sun 3/91:03 pmDCA - MDW
1 stop12h 16mFrontier
Tue 3/116:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 2/19$160
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 4/158:55 pmDCA - MDW
Nonstop2h 00mSouthwest
Mon 4/217:20 amMDW - DCA
Nonstop1h 50mSouthwest
Deal found 2/20$177
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/66:00 amIAD - MDW
1 stop3h 51mDelta
Tue 3/116:42 pmMDW - IAD
1 stop3h 18mDelta
Deal found 2/19$197
This Delta deal was found by Cheapflights users on 2/20. 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 4/262:00 pmDCA - MDW
1 stop4h 59mDelta
Tue 4/2912:48 pmMDW - DCA
1 stop6h 46mDelta
Deal found 2/20$217
This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/263:58 pmIAD - MDW
1 stop16h 17mMultiple Airlines
Sat 6/286:44 pmMDW - IAD
1 stop24h 47mMultiple Airlines
Deal found 2/19$340
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 10/3112:34 pmIAD - MDW
1 stop6h 57mAllegiant Air
Sun 11/24:46 pmMDW - IAD
2 stops23h 29mAllegiant Air
Deal found 2/20$441

Find flights from District of Columbia to Midway within your budget

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 February 20, 2025.

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 3/6

10:25 pm-9:25 pm

1 stop24h 00m

Chicago Midway

Mon 3/10

4:20 pm-1:16 pm

1 stop19h 56m

$159

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 3/9

1:03 pm-12:19 am

1 stop12h 16m

Chicago Midway

Tue 3/11

6:40 am-4:59 pm

1 stop9h 19m

$160

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/15

8:55 pm-9:55 pm

Nonstop2h 00m

Chicago Midway

Mon 4/21

7:20 am-10:10 am

Nonstop1h 50m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/6

6:00 am-8:51 am

1 stop3h 51m

Chicago Midway

Tue 3/11

6:42 pm-11:00 pm

1 stop3h 18m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 4/26

2:00 pm-5:59 pm

1 stop4h 59m

Chicago Midway

Tue 4/29

12:48 pm-8:34 pm

1 stop6h 46m

$217

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/26

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Sat 6/28

6:44 pm-8:31 pm

1 stop24h 47m

$340

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/19

9:21 am-9:44 am

2 stops25h 23m

Chicago Midway

Sun 6/22

11:45 am-2:23 pm

2 stops25h 38m

$488

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/17

9:18 pm-8:01 am

1 stop11h 43m

$81

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 3/27

1:03 pm-12:17 am

1 stop12h 14m

$81

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 3/31

9:00 pm-10:05 pm

Nonstop2h 05m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from District of Columbia to Midway

Get recent, data-driven insights about flights from District of Columbia to Midway including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($81), Southwest ($89), and Delta ($97).

  • 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
New Buffalo
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$190FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$165Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$339FlexibilityNo cancel feeOn-timeN/A
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