HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
District of Columbia

$75+ Cheap flights from Midway (MDW) to District of Columbia

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — IAD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to District of Columbia with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Midway to District of Columbia

Cheapest flights from Midway to District of Columbia
Explore the most affordable flight options available from Midway to District of Columbia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:14 amMDW - IAD
1 stop9h 23mFrontier
Tue 12/305:37 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 10/28$146
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Tue 12/235:37 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 10/28$147
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:30 pmMDW - DCA
1 stop8h 29mFrontier
Wed 11/128:15 amDCA - MDW
1 stop28h 15mFrontier
Deal found 10/28$150
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Tue 11/111:56 pmMDW - IAD
1 stop5h 24mFrontier
Sat 11/158:36 pmIAD - MDW
1 stop13h 36mFrontier
Deal found 10/30$150
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:18 pmMDW - DCA
1 stop8h 41mFrontier
Thu 12/116:00 pmDCA - MDW
1 stop18h 08mFrontier
Deal found 10/29$152
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:05 amMDW - IAD
1 stop10h 41mFrontier
Thu 12/47:18 pmIAD - MDW
1 stop27h 54mFrontier
Deal found 10/30$154
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - IAD
1 stop11h 04mFrontier
Tue 12/305:37 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 10/28$156
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:56 pmMDW - IAD
1 stop5h 24mFrontier
Thu 12/117:18 pmIAD - MDW
1 stop25h 24mFrontier
Deal found 10/27$157
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/191:56 pmMDW - IAD
1 stop5h 24mMultiple Airlines
Fri 11/213:00 pmIAD - MDW
1 stop4h 46mMultiple Airlines
Deal found 10/29$160
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:42 pmMDW - IAD
2 stops22h 42mMultiple Airlines
Sun 12/75:26 pmIAD - MDW
1 stop5h 46mMultiple Airlines
Deal found 10/28$161
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/41:56 pmMDW - IAD
1 stop5h 24mFrontier
Sat 11/158:36 pmIAD - MDW
1 stop13h 36mFrontier
Deal found 10/28$163
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:56 pmMDW - IAD
1 stop5h 24mMultiple Airlines
Fri 11/213:00 pmIAD - MDW
1 stop4h 46mMultiple Airlines
Deal found 10/29$164

Cheap flight deals from Midway to District of Columbia

Keep the following information in mind while searching for Midway to District of Columbia flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$150
(Priceline)

One-way from

$75
(Priceline)

Popular in

January

Cheapest in

August

Average price

$257

Good round-trip deal

$263 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago Midway to District of Columbia
Search Deals
One-way flight from Chicago Midway to District of Columbia
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to District of Columbia.
Search Deals
Price to beat on a one-way flight from Chicago Midway to District of Columbia.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to District of Columbia 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 October 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to District of Columbia that are best for you.

Fly from

Midway

Fly to

District of Columbia

Route

Depart

Return

Price

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 11/6

1:37 pm-12:11 am

1 stop9h 34m

Washington, D.C. Dulles Intl

Mon 11/10

5:44 pm-10:11 pm

1 stop5h 27m

$176

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 11/6

6:25 am-4:34 pm

1 stop9h 09m

Washington, D.C. Dulles Intl

Fri 11/7

5:34 pm-10:08 pm

1 stop5h 34m

$236

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Thu 12/4

5:40 pm-8:30 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Mon 12/8

8:45 pm-9:55 pm

Nonstop2h 10m

$237

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Mon 12/8

12:15 pm-3:00 pm

Nonstop1h 45m

Washington, D.C. Reagan-National

Thu 12/11

6:55 pm-8:00 pm

Nonstop2h 05m

$237

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Mon 1/12

8:25 am-3:25 pm

1 stop6h 00m

Washington, D.C. Reagan-National

Wed 1/14

3:25 pm-4:40 pm

Nonstop2h 15m

$247

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 11/19

5:40 pm-8:30 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 12/3

6:55 pm-8:00 pm

Nonstop2h 05m

$253

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 12/6

10:40 am-1:30 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Tue 12/9

8:45 pm-9:55 pm

Nonstop2h 10m

$254

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 11/8

11:36 am-7:51 pm

1 stop7h 15m

Washington, D.C. Dulles Intl

Sun 11/9

5:29 pm-10:03 pm

1 stop5h 34m

$256

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 11/18

5:34 pm-11:41 pm

1 stop5h 07m

Washington, D.C. Reagan-National

Thu 12/11

6:00 am-9:54 am

1 stop4h 54m

$257

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 11/18

1:15 pm-6:59 pm

1 stop4h 44m

Washington, D.C. Reagan-National

Sat 12/13

6:06 am-8:49 am

1 stop3h 43m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 37 results
1
2
3
4

Best time to book a flight from Midway to District of Columbia

Have a flexible travel schedule? Discover the best time to fly to District of Columbia from Midway 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 Chicago Midway Airport to District of Columbia

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

Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $57). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $169). 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 MDW to DC?

Find hourly flight availability from Midway to District of Columbia. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to District of Columbia is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 25% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to District of Columbia?

Use this chart to determine the cheapest time to fly round-trip from Midway to District of Columbia. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to District of Columbia flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing District of Columbia

Get insights into the airlines that provide service to District of Columbia. 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 District of Columbia. Reviews last updated October 30, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to District of Columbia, such as Southwest, Delta, and Frontier. 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
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,993 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

  • How long is the flight from Chicago Midway Airport to District of Columbia?

    Frontier, Southwest, and Delta can get you from Chicago Midway Airport to District of Columbia in just under 1h 50m. Your travel time can differ by up to 7h 44m. Chicago Midway Airport and District of Columbia are separated by a distance of 599 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to District of Columbia 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 Chicago Midway Airport to District of Columbia?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to District of Columbia (average of $57). Flying from Chicago Midway Airport to District of Columbia in April is currently the most expensive (average of $169). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to District of Columbia

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Atlanta flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Seattle flights
O'Hare Intl to Boston flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Ontario flights
O'Hare Intl to Baltimore flights
Midway to John F Kennedy Intl flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Santa Ana flights
Midway to Miami flights
Midway to LaGuardia flights
Midway to Los Angeles flights
Midway to Atlanta flights
O'Hare Intl to Austin flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Hobby flights
O'Hare Intl to San Diego flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Honolulu flights
Midway to Orlando flights
Midway to Baltimore flights
O'Hare Intl to Nashville flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Philadelphia flights
Midway to Sky Harbor Intl flights
Midway to Hobby flights
Midway to Denver flights
Midway to Las Vegas flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Love Field flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights

Top 3 airlines flying from Midway to District of Columbia

Discover the top 3 airlines that operate flights from Midway to District of Columbia. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$228FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$296FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$433FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.