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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $74

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. Dulles Intl Airport to Chicago departing on 4/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:27 pm - 10:28 pm
IAD
-
MDW
6h 01m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
IAD
3h 25m
1 stop
$188Delta
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
7:05 am - 7:59 am
IAD
-
MDW
25h 54m
2 stops
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$189Frontier
Sat, Apr 18 - Tue, Apr 21
Frontier Logo
6:15 am - 10:19 pm
IAD
-
MDW
17h 04m
1 stop
Frontier Logo
6:00 am - 5:34 pm
MDW
-
IAD
10h 34m
1 stop
$191Frontier
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
6:10 am - 7:31 pm
IAD
-
MDW
14h 21m
1 stop
Frontier Logo
6:00 am - 12:36 am
MDW
-
IAD
17h 36m
1 stop
$192Frontier
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
10:25 pm - 1:00 pm
IAD
-
MDW
15h 35m
2 stops
Multiple Airlines Logo
6:00 am - 5:34 pm
MDW
-
IAD
10h 34m
1 stop
$194Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
6:00 am - 9:50 pm
IAD
-
MDW
16h 50m
2 stops
Frontier Logo
7:34 pm - 8:56 am
MDW
-
IAD
12h 22m
1 stop
$196Frontier
Fri, Apr 24 - Sat, Apr 25
Multiple Airlines Logo
8:12 am - 10:19 pm
IAD
-
MDW
15h 07m
2 stops
Multiple Airlines Logo
2:20 pm - 12:36 am
MDW
-
IAD
9h 16m
1 stop
$197Multiple Airlines
Mon, May 4 - Wed, May 6
Delta Logo
6:00 am - 8:53 am
IAD
-
MDW
3h 53m
1 stop
Delta Logo
6:34 pm - 10:59 pm
MDW
-
IAD
3h 25m
1 stop
$199Delta
Tue, Mar 24 - Tue, Apr 7
Frontier Logo
7:00 am - 3:33 pm
IAD
-
MDW
9h 33m
2 stops
Frontier Logo
2:56 pm - 12:36 am
MDW
-
IAD
8h 40m
1 stop
$201Frontier
Tue, Mar 24 - Tue, Apr 7
Frontier Logo
9:51 am - 7:31 pm
IAD
-
MDW
10h 40m
1 stop
Frontier Logo
2:20 pm - 12:36 am
MDW
-
IAD
9h 16m
1 stop
$202Frontier
Thu, May 14 - Sun, May 17

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

Our best Delta deals on Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flight tickets
Delta
Apr 17
IAD5:27 pmWashington, D.C. Dulles Intl
6h 01m
1 stop
MDW10:28 pmChicago Midway
Apr 20
MDW6:38 pmChicago Midway
3h 25m
1 stop
IAD11:03 pmWashington, D.C. Dulles Intl
$188
Delta
Mar 24
IAD6:00 amWashington, D.C. Dulles Intl
3h 53m
1 stop
MDW8:53 amChicago Midway
Apr 7
MDW6:34 pmChicago Midway
3h 25m
1 stop
IAD10:59 pmWashington, D.C. Dulles Intl
$199
Delta
Mar 25
IAD6:00 amWashington, D.C. Dulles Intl
3h 53m
1 stop
MDW8:53 amChicago Midway
Apr 1
MDW6:34 pmChicago Midway
3h 25m
1 stop
IAD10:59 pmWashington, D.C. Dulles Intl
$217

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

Our best Frontier deals on Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flight tickets
Frontier
Apr 18
IAD7:05 amWashington, D.C. Dulles Intl
25h 54m
2 stops
MDW7:59 amChicago Midway
Apr 21
MDW2:15 pmChicago Midway
9h 21m
1 stop
IAD12:36 amWashington, D.C. Dulles Intl
$189
Frontier
Apr 13
IAD6:15 amWashington, D.C. Dulles Intl
17h 04m
1 stop
MDW10:19 pmChicago Midway
Apr 20
MDW6:00 amChicago Midway
10h 34m
1 stop
IAD5:34 pmWashington, D.C. Dulles Intl
$191
Frontier
Apr 30
IAD6:10 amWashington, D.C. Dulles Intl
14h 21m
1 stop
MDW7:31 pmChicago Midway
May 3
MDW6:00 amChicago Midway
17h 36m
1 stop
IAD12:36 amWashington, D.C. Dulles Intl
$192

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Dulles Intl Airport to Chicago Midway 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 March 2, 2026.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/17

5:27 pm-10:28 pm

1 stop6h 01m

Chicago Midway

Mon 4/20

6:38 pm-11:03 pm

1 stop3h 25m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 4/18

7:05 am-7:59 am

2 stops25h 54m

Chicago Midway

Tue 4/21

2:15 pm-12:36 am

1 stop9h 21m

$189

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

6:15 am-10:19 pm

1 stop17h 04m

Chicago Midway

Mon 4/20

6:00 am-5:34 pm

1 stop10h 34m

$191

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/30

6:10 am-7:31 pm

1 stop14h 21m

Chicago Midway

Sun 5/3

6:00 am-12:36 am

1 stop17h 36m

$192

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Mon 4/20

6:00 am-5:34 pm

1 stop10h 34m

$194

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/24

6:00 am-9:50 pm

2 stops16h 50m

Chicago Midway

Sat 4/25

7:34 pm-8:56 am

1 stop12h 22m

$196

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 5/4

8:12 am-10:19 pm

2 stops15h 07m

Chicago Midway

Wed 5/6

2:20 pm-12:36 am

1 stop9h 16m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 3/24

6:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Tue 4/7

6:34 pm-10:59 pm

1 stop3h 25m

$199

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 3/24

7:00 am-3:33 pm

2 stops9h 33m

Chicago Midway

Tue 4/7

2:56 pm-12:36 am

1 stop8h 40m

$201

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/14

9:51 am-7:31 pm

1 stop10h 40m

Chicago Midway

Sun 5/17

2:20 pm-12:36 am

1 stop9h 16m

$202

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 Chicago from

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Washington, D.C. Dulles Intl Airport. The lowest ticket price found for a Wednesday departure recently was $318. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Washington, D.C. Dulles Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $378.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Washington, D.C. Dulles Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $309 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $356. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

Fastest flight time

3h 42m

Direct flights

None
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport takes 3h 42m
There are no direct flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport. There are no popular flight routes from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport.
Search flight deals

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

    A flight from Washington, D.C. Dulles Intl to Chicago Midway will travel around 575.6 mi. 3h 42m is a normal flight duration for this route.

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

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

  • How many operators does momondo search for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

Best airlines flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $135Free CancellationRating
5.7
3,039 reviews
Search Frontier flights
DeltaPriceFrom $194Free CancellationRating
7.9
8,237 reviews
Search Delta flights

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Washington, D.C. to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Washington, D.C. to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

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 Washington, D.C. to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Washington, D.C.. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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