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Cheap flights from Chicago Midway Airport to Washington, D.C. from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Washington, D.C. departing on 9/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Washington, D.C.

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:03 pm - 12:28 am
MDW
-
IAD
11h 25m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$200Frontier
Wed, Sep 23 - Sat, Sep 26
Delta Logo
6:45 pm - 11:11 pm
MDW
-
IAD
3h 26m
1 stop
Delta Logo
6:10 am - 8:45 am
IAD
-
MDW
3h 35m
1 stop
$207Delta
Mon, Nov 2 - Thu, Nov 12
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$220Frontier
Tue, Aug 18 - Wed, Aug 19
Frontier Logo
7:25 am - 5:36 pm
MDW
-
IAD
9h 11m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$221Frontier
Tue, Sep 15 - Tue, Sep 29
Frontier Logo
11:06 am - 10:52 pm
MDW
-
IAD
10h 46m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$224Frontier
Mon, Aug 17 - Tue, Aug 18
Frontier Logo
6:40 am - 5:36 pm
MDW
-
IAD
9h 56m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$230Frontier
Wed, Oct 21 - Fri, Oct 23
Delta Logo
5:45 pm - 11:26 pm
MDW
-
IAD
4h 41m
1 stop
Delta Logo
6:09 pm - 10:44 pm
IAD
-
MDW
5h 35m
1 stop
$231Delta
Sat, Sep 5 - Sat, Sep 12
Frontier Logo
11:06 am - 10:52 pm
MDW
-
IAD
10h 46m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$234Frontier
Mon, Aug 17 - Wed, Aug 19
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$235Frontier
Wed, Aug 19 - Sun, Aug 23
Frontier Logo
12:03 pm - 12:28 am
MDW
-
IAD
11h 25m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$236Frontier
Fri, Nov 6 - Tue, Nov 10

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Delta flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

Our best Delta deals on Chicago Midway Airport to Washington, D.C. Dulles Intl Airport flight tickets
Delta
Sep 5
MDW4:39 pmChicago Midway
6h 55m
1 stop
IAD12:34 amWashington, D.C. Dulles Intl
Sep 6
IAD6:10 amWashington, D.C. Dulles Intl
4h 07m
1 stop
MDW9:17 amChicago Midway
$207
Delta
Sep 5
MDW5:45 pmChicago Midway
4h 41m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
Sep 12
IAD6:09 pmWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:44 pmChicago Midway
$231
Delta
Sep 3
MDW6:05 amChicago Midway
4h 28m
1 stop
IAD11:33 amWashington, D.C. Dulles Intl
Sep 5
IAD5:47 pmWashington, D.C. Dulles Intl
5h 49m
1 stop
MDW10:36 pmChicago Midway
$257

Frontier flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

Our best Frontier deals on Chicago Midway Airport to Washington, D.C. Dulles Intl Airport flight tickets
Frontier
Aug 18
MDW11:50 amChicago Midway
10h 02m
1 stop
IAD10:52 pmWashington, D.C. Dulles Intl
Aug 19
IAD6:20 amWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:55 amChicago Midway
$220
Frontier
Sep 15
MDW7:25 amChicago Midway
9h 11m
1 stop
IAD5:36 pmWashington, D.C. Dulles Intl
Sep 29
IAD7:00 amWashington, D.C. Dulles Intl
4h 58m
1 stop
MDW10:58 amChicago Midway
$221
Frontier
Aug 17
MDW11:06 amChicago Midway
10h 46m
1 stop
IAD10:52 pmWashington, D.C. Dulles Intl
Aug 18
IAD6:20 amWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:55 amChicago Midway
$224

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport 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, momondo users made 832,500 searches. Data last updated July 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 9/23

12:03 pm-12:28 am

1 stop11h 25m

Washington, D.C. Dulles Intl

Sat 9/26

7:00 am-10:58 am

1 stop4h 58m

$200
Quickest round-trip

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 11/2

6:45 pm-11:11 pm

1 stop3h 26m

Washington, D.C. Dulles Intl

Thu 11/12

6:10 am-8:45 am

1 stop3h 35m

$207

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Tue 8/18

11:50 am-10:52 pm

1 stop10h 02m

Washington, D.C. Dulles Intl

Wed 8/19

6:20 am-10:55 am

1 stop5h 35m

$220

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Tue 9/15

7:25 am-5:36 pm

1 stop9h 11m

Washington, D.C. Dulles Intl

Tue 9/29

7:00 am-10:58 am

1 stop4h 58m

$221

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 8/17

11:06 am-10:52 pm

1 stop10h 46m

Washington, D.C. Dulles Intl

Tue 8/18

6:20 am-10:55 am

1 stop5h 35m

$224

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 10/21

6:40 am-5:36 pm

1 stop9h 56m

Washington, D.C. Dulles Intl

Fri 10/23

7:00 am-10:58 am

1 stop4h 58m

$230

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 9/5

5:45 pm-11:26 pm

1 stop4h 41m

Washington, D.C. Dulles Intl

Sat 9/12

6:09 pm-10:44 pm

1 stop5h 35m

$231

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 8/17

11:06 am-10:52 pm

1 stop10h 46m

Washington, D.C. Dulles Intl

Wed 8/19

6:20 am-10:55 am

1 stop5h 35m

$234

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 8/19

6:05 am-5:14 pm

1 stop10h 09m

Washington, D.C. Dulles Intl

Sun 8/23

6:20 am-10:55 am

1 stop5h 35m

$235

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 11/6

12:03 pm-12:28 am

1 stop11h 25m

Washington, D.C. Dulles Intl

Tue 11/10

7:00 am-10:58 am

1 stop4h 58m

$236

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Washington, D.C. from

How to get the cheapest flight ticket from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Washington, D.C. Dulles Intl Airport?

Our data shows that Friday is the least expensive day to fly to Washington, D.C. Dulles Intl Airport. Tickets to fly out on this day can be as low as $587. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport for around $903.

What is the cheapest time of day to depart on your flight to Washington, D.C. Dulles Intl Airport?

Flying to Washington, D.C. Dulles Intl Airport from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $599 when looking at flights departing in the morning. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $1,008 on average. Flights to Washington, D.C. Dulles Intl Airport from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Washington, D.C. Dulles Intl Airport (MDW to IAD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

Fastest flight time

3h 26m

Direct flights

None
The fastest flight from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport takes 3h 26m
There are no direct flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport. There are no popular flight routes from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport.
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Frequently asked questions about flying from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport

  • How far is Chicago Midway to Washington, D.C. Dulles Intl by plane?

    The straight-line distance from Chicago Midway to Washington, D.C. Dulles Intl is 575.6 mi. By plane, this route typically takes 3h 26m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport?

    Prices for flights from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Washington, D.C. Dulles Intl Airport.

  • What documentation or ID do you need to fly to Washington, D.C. Dulles Intl Airport?

    The necessary travel and health documents for your Washington, D.C. Dulles Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Washington, D.C.?

Book flights to Washington, D.C. if you plan to visit one of these locations
Alexandria
National Harbor
Arlington
Gettysburg
Winchester
Waldorf
Laurel
Woodbridge
Fredericksburg
Gaithersburg
Linthicum Heights
Rockville
Manassas
Towson
Silver Spring
Colonial Beach
Sterling
Springfield
Tysons
Fairfax

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Washington, D.C.?

Finding the right flight to Washington, D.C. from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Washington, D.C. quick and easy, saving you time and money.

Can I find flights from Chicago to Washington, D.C. with flexible booking policies on momondo?

momondo does allow users to show only those flights to Washington, D.C. from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Washington, D.C.?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Washington, D.C..

I’m not ready to book a flight from Chicago to Washington, D.C. right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Washington, D.C. now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Washington, D.C. and let you know when they change.

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