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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago 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 Washington, D.C. Dulles Intl Airport to Chicago departing on 8/11. 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

Discover deals from 900+ travel sites with momondo.

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.
Frontier Logo
12:28 pm - 10:03 pm
IAD
-
MDW
10h 35m
2 stops
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
$241Frontier
Wed, Aug 12 - Tue, Aug 18
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
Frontier Logo
12:03 pm - 12:28 am
MDW
-
IAD
11h 25m
1 stop
$246Frontier
Tue, Oct 27 - Fri, Nov 6
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$247Frontier
Thu, Aug 20 - Tue, Aug 25
Frontier Logo
6:49 am - 11:07 am
IAD
-
MDW
5h 18m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$248Frontier
Sat, Aug 1 - Wed, Aug 5
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
$249Frontier
Fri, Aug 21 - Mon, Aug 24
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$250Frontier
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
$251Frontier
Thu, Aug 20 - Mon, Aug 24
Delta Logo
5:47 pm - 10:36 pm
IAD
-
MDW
5h 49m
1 stop
Delta Logo
6:05 am - 11:33 am
MDW
-
IAD
4h 28m
1 stop
$252Delta
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
9:26 pm - 5:14 pm
MDW
-
IAD
18h 48m
2 stops
$253Frontier
Wed, Aug 26 - Thu, Aug 27
Frontier Logo
8:33 pm - 9:51 am
IAD
-
MDW
14h 18m
1 stop
Frontier Logo
11:06 am - 10:52 pm
MDW
-
IAD
10h 46m
1 stop
$254Frontier
Sat, Aug 8 - Sat, Aug 15

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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
Aug 12
IAD12:28 pmWashington, D.C. Dulles Intl
10h 35m
2 stops
MDW10:03 pmChicago Midway
Aug 18
MDW11:50 amChicago Midway
10h 02m
1 stop
IAD10:52 pmWashington, D.C. Dulles Intl
$241
Frontier
Aug 12
IAD12:28 pmWashington, D.C. Dulles Intl
10h 35m
2 stops
MDW10:03 pmChicago Midway
Aug 18
MDW11:50 amChicago Midway
10h 02m
1 stop
IAD10:52 pmWashington, D.C. Dulles Intl
$246
Frontier
Aug 20
IAD6:20 amWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:55 amChicago Midway
Aug 25
MDW6:05 amChicago Midway
10h 09m
1 stop
IAD5:14 pmWashington, D.C. Dulles Intl
$247

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
Aug 6
IAD5:47 pmWashington, D.C. Dulles Intl
5h 49m
1 stop
MDW10:36 pmChicago Midway
Aug 10
MDW6:05 amChicago Midway
4h 28m
1 stop
IAD11:33 amWashington, D.C. Dulles Intl
$252
Delta
Sep 3
IAD6:00 amWashington, D.C. Dulles Intl
4h 59m
1 stop
MDW9:59 amChicago Midway
Sep 5
MDW9:24 amChicago Midway
6h 14m
1 stop
IAD4:38 pmWashington, D.C. Dulles Intl
$261
Delta
Sep 10
IAD6:09 pmWashington, D.C. Dulles Intl
5h 36m
1 stop
MDW10:45 pmChicago Midway
Sep 12
MDW9:29 amChicago Midway
6h 01m
1 stop
IAD4:30 pmWashington, D.C. Dulles Intl
$263

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 July 13, 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

Wed 8/12

12:28 pm-10:03 pm

2 stops10h 35m

Chicago Midway

Tue 8/18

11:50 am-10:52 pm

1 stop10h 02m

$241

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 10/27

7:00 am-10:58 am

1 stop4h 58m

Chicago Midway

Fri 11/6

12:03 pm-12:28 am

1 stop11h 25m

$246

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/20

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Tue 8/25

6:05 am-5:14 pm

1 stop10h 09m

$247

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/1

6:49 am-11:07 am

1 stop5h 18m

Chicago Midway

Wed 8/5

6:05 am-5:14 pm

1 stop10h 09m

$248

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 8/21

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Mon 8/24

11:50 am-10:52 pm

1 stop10h 02m

$249

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/27

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Sun 8/30

6:05 am-5:14 pm

1 stop10h 09m

$250

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/20

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Mon 8/24

11:50 am-10:52 pm

1 stop10h 02m

$251
Quickest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/6

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Mon 8/10

6:05 am-11:33 am

1 stop4h 28m

$252

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 8/26

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Thu 8/27

9:26 pm-5:14 pm

2 stops18h 48m

$253

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/8

8:33 pm-9:51 am

1 stop14h 18m

Chicago Midway

Sat 8/15

11:06 am-10:52 pm

1 stop10h 46m

$254

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 month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Dulles Intl Airport, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Washington, D.C. Dulles Intl Airport during the month December is also very affordable. Most momondo users find prices during this month for around $135.

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 $334. 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, Monday 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 $416.

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 $378. 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 35m

Direct flights

None
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport takes 3h 35m
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. 3h 35m 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 $130Free CancellationRating
5.6
2,816 reviews
Search Frontier flights
DeltaPriceFrom $149Free CancellationRating
7.8
8,463 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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