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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $81

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 10/24. 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.
Frontier Logo
8:40 am - 12:41 pmIAD-MDW
29h 01m1 stop
Frontier Logo
6:15 am - 4:34 pmMDW-IAD
9h 19m1 stop
$141Frontier
Find Deal
Tue, Nov 4 - Fri, Nov 7
Frontier Logo
8:40 am - 12:41 pmIAD-MDW
29h 01m1 stop
Frontier Logo
1:56 pm - 8:20 pmMDW-IAD
5h 24m1 stop
$143Frontier
Find Deal
Tue, Nov 4 - Tue, Nov 11
Frontier Logo
1:21 pm - 11:05 pmIAD-MDW
10h 44m1 stop
Frontier Logo
6:00 am - 12:49 pmMDW-IAD
5h 49m1 stop
$146Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
2:06 pm - 8:20 pmMDW-IAD
5h 14m1 stop
$147Frontier
Find Deal
Wed, Oct 22 - Wed, Nov 12
Frontier Logo
8:47 am - 12:41 pmIAD-MDW
4h 54m1 stop
Frontier Logo
2:06 pm - 8:20 pmMDW-IAD
5h 14m1 stop
$148Frontier
Find Deal
Wed, Oct 29 - Wed, Nov 5
Frontier Logo
8:47 am - 12:41 pmIAD-MDW
4h 54m1 stop
Frontier Logo
2:06 pm - 8:20 pmMDW-IAD
5h 14m1 stop
$149Frontier
Find Deal
Wed, Oct 29 - Wed, Nov 5
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
1:37 pm - 11:29 pmMDW-IAD
8h 52m1 stop
$150Frontier
Find Deal
Wed, Oct 22 - Thu, Oct 30
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$151Frontier
Find Deal
Tue, Oct 21 - Wed, Oct 22
Multiple Airlines Logo
8:40 am - 11:55 pmIAD-MDW
16h 15m2 stops
Multiple Airlines Logo
6:15 am - 12:11 amMDW-IAD
16h 56m1 stop
$169Multiple Airlines
Find Deal
Tue, Nov 4 - Fri, Nov 7
Multiple Airlines Logo
1:34 pm - 7:34 pmIAD-MDW
7h 00m1 stop
Multiple Airlines Logo
2:06 pm - 8:20 pmMDW-IAD
5h 14m1 stop
$171Multiple Airlines
Find Deal
Mon, Oct 27 - Wed, Oct 29

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
Nov 4
IAD8:40 amWashington, D.C. Dulles Intl
29h 01m
1 stop
MDW12:41 pmChicago Midway
Nov 7
MDW6:15 amChicago Midway
9h 19m
1 stop
IAD4:34 pmWashington, D.C. Dulles Intl
$141
Find similar
Frontier
Nov 4
IAD8:40 amWashington, D.C. Dulles Intl
29h 01m
1 stop
MDW12:41 pmChicago Midway
Nov 11
MDW1:56 pmChicago Midway
5h 24m
1 stop
IAD8:20 pmWashington, D.C. Dulles Intl
$143
Find similar
Frontier
Dec 5
IAD1:21 pmWashington, D.C. Dulles Intl
10h 44m
1 stop
MDW11:05 pmChicago Midway
Dec 8
MDW6:00 amChicago Midway
5h 49m
1 stop
IAD12:49 pmWashington, D.C. Dulles Intl
$146
Find similar

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 October 9, 2025.
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

Tue 11/4

8:40 am-12:41 pm

1 stop29h 01m

Chicago Midway

Fri 11/7

6:15 am-4:34 pm

1 stop9h 19m

$141

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 11/4

8:40 am-12:41 pm

1 stop29h 01m

Chicago Midway

Tue 11/11

1:56 pm-8:20 pm

1 stop5h 24m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 12/5

1:21 pm-11:05 pm

1 stop10h 44m

Chicago Midway

Mon 12/8

6:00 am-12:49 pm

1 stop5h 49m

$146

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/22

9:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Wed 11/12

2:06 pm-8:20 pm

1 stop5h 14m

$147

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/29

8:47 am-12:41 pm

1 stop4h 54m

Chicago Midway

Wed 11/5

2:06 pm-8:20 pm

1 stop5h 14m

$148

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/29

8:47 am-12:41 pm

1 stop4h 54m

Chicago Midway

Wed 11/5

2:06 pm-8:20 pm

1 stop5h 14m

$149

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/22

9:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Thu 10/30

1:37 pm-11:29 pm

1 stop8h 52m

$150

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 10/21

9:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Wed 10/22

8:05 am-7:46 pm

1 stop10h 41m

$151

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 11/4

8:40 am-11:55 pm

2 stops16h 15m

Chicago Midway

Fri 11/7

6:15 am-12:11 am

1 stop16h 56m

$169

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 10/27

1:34 pm-7:34 pm

1 stop7h 00m

Chicago Midway

Wed 10/29

2:06 pm-8:20 pm

1 stop5h 14m

$171

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 $317. 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 $380.

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 $313 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $353. 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

Direct flights

None
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.
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  • 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 54m 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 $144Free CancellationRating
5.8
3,144 reviews
Search Frontier flights
DeltaPriceFrom $234Free CancellationRating
7.9
7,968 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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