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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $108

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 4/29. 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.
Multiple Airlines Logo
5:26 pm - 10:02 pm
IAD
-
MDW
5h 36m
1 stop
Multiple Airlines Logo
9:14 am - 5:28 pm
MDW
-
IAD
7h 14m
1 stop
$219Multiple Airlines
Sat, May 9 - Thu, May 21
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$220Frontier
Thu, May 28 - Tue, Jun 2
Frontier Logo
7:27 pm - 2:12 pm
IAD
-
MDW
19h 45m
2 stops
Frontier Logo
6:00 am - 11:09 pm
MDW
-
IAD
16h 09m
1 stop
$221Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
6:00 am - 5:27 pm
MDW
-
IAD
10h 27m
1 stop
$222Frontier
Thu, May 28 - Fri, May 29
Frontier Logo
8:47 pm - 11:04 am
IAD
-
MDW
15h 17m
1 stop
Frontier Logo
12:27 pm - 11:09 pm
MDW
-
IAD
9h 42m
1 stop
$223Frontier
Fri, Jun 5 - Sun, Jun 7
Frontier Logo
5:26 pm - 10:02 pm
IAD
-
MDW
5h 36m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$224Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
11:12 am - 10:02 pm
IAD
-
MDW
11h 50m
1 stop
Frontier Logo
6:00 am - 5:12 pm
MDW
-
IAD
10h 12m
1 stop
$225Frontier
Fri, May 15 - Mon, May 18
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
12:04 pm - 11:17 pm
MDW
-
IAD
10h 13m
1 stop
$226Frontier
Sun, Jun 7 - Wed, Jun 10
Delta Logo
5:33 pm - 9:09 pm
IAD
-
MDW
4h 36m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
Mon, May 11 - Tue, May 12
Frontier Logo
12:56 pm - 10:02 pm
IAD
-
MDW
10h 06m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$229Frontier
Thu, May 21 - Tue, May 26

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
May 28
IAD11:07 amWashington, D.C. Dulles Intl
11h 55m
1 stop
MDW10:02 pmChicago Midway
Jun 2
MDW6:00 amChicago Midway
9h 21m
1 stop
IAD4:21 pmWashington, D.C. Dulles Intl
$220
Frontier
May 28
IAD7:27 pmWashington, D.C. Dulles Intl
19h 45m
2 stops
MDW2:12 pmChicago Midway
Jun 1
MDW6:00 amChicago Midway
16h 09m
1 stop
IAD11:09 pmWashington, D.C. Dulles Intl
$221
Frontier
May 28
IAD11:07 amWashington, D.C. Dulles Intl
11h 55m
1 stop
MDW10:02 pmChicago Midway
May 29
MDW6:00 amChicago Midway
10h 27m
1 stop
IAD5:27 pmWashington, D.C. Dulles Intl
$222

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
May 11
IAD5:33 pmWashington, D.C. Dulles Intl
4h 36m
1 stop
MDW9:09 pmChicago Midway
May 12
MDW6:36 pmChicago Midway
3h 20m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$228
Delta
Apr 27
IAD5:27 pmWashington, D.C. Dulles Intl
6h 01m
1 stop
MDW10:28 pmChicago Midway
May 13
MDW6:36 pmChicago Midway
3h 20m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$236
Delta
Jun 15
IAD6:00 amWashington, D.C. Dulles Intl
4h 14m
1 stop
MDW9:14 amChicago Midway
Jun 18
MDW12:45 pmChicago Midway
7h 19m
1 stop
IAD9:04 pmWashington, D.C. Dulles Intl
$238

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 April 18, 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

Cheapest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/9

5:26 pm-10:02 pm

1 stop5h 36m

Chicago Midway

Thu 5/21

9:14 am-5:28 pm

1 stop7h 14m

$219

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Tue 6/2

6:00 am-4:21 pm

1 stop9h 21m

$220

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

7:27 pm-2:12 pm

2 stops19h 45m

Chicago Midway

Mon 6/1

6:00 am-11:09 pm

1 stop16h 09m

$221

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Fri 5/29

6:00 am-5:27 pm

1 stop10h 27m

$222

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 6/5

8:47 pm-11:04 am

1 stop15h 17m

Chicago Midway

Sun 6/7

12:27 pm-11:09 pm

1 stop9h 42m

$223

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/14

5:26 pm-10:02 pm

1 stop5h 36m

Chicago Midway

Sun 5/17

6:00 am-4:21 pm

1 stop9h 21m

$224

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 5/15

11:12 am-10:02 pm

1 stop11h 50m

Chicago Midway

Mon 5/18

6:00 am-5:12 pm

1 stop10h 12m

$225

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 6/7

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Wed 6/10

12:04 pm-11:17 pm

1 stop10h 13m

$226
Quickest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 5/11

5:33 pm-9:09 pm

1 stop4h 36m

Chicago Midway

Tue 5/12

6:36 pm-10:56 pm

1 stop3h 20m

$228

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/21

12:56 pm-10:02 pm

1 stop10h 06m

Chicago Midway

Tue 5/26

6:00 am-4:21 pm

1 stop9h 21m

$229

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 typical price of a round-trip flight between Washington, D.C. Dulles Intl Airport and Chicago Midway Airport?

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Washington, D.C. Dulles Intl Airport. The lowest ticket price found for a Saturday departure recently was $328. 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 $384.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $364. 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

4h 14m

Direct flights

None
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport takes 4h 14m
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

Frequently asked questions about flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport

  • 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. 4h 14m 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
2,987 reviews
Search Frontier flights
DeltaPriceFrom $194Free CancellationRating
7.9
8,424 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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