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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $79

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 9/10. 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 (IAD-MDW)

Cheap round-trip flights

Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
5:15 pm - 12:15 amMDW-IAD
6h 00m1 stop
$142Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
5:15 pm - 12:15 amMDW-IAD
6h 00m1 stop
$143Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
9:00 am - 7:55 pmMDW-IAD
9h 55m1 stop
$144Frontier
Find Deal
Fri, Sep 5 - Wed, Sep 10
Frontier Logo
4:22 pm - 10:47 pmIAD-MDW
7h 25m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$146Frontier
Find Deal
Sat, Oct 11 - Tue, Oct 14
Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
6:21 am - 9:19 pmMDW-IAD
13h 58m1 stop
$148Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
6:21 am - 9:24 pmMDW-IAD
14h 03m1 stop
$149Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
7:14 pm - 9:18 amIAD-MDW
15h 04m1 stop
Frontier Logo
5:20 pm - 12:15 amMDW-IAD
5h 55m1 stop
$150Frontier
Find Deal
Sat, Oct 4 - Mon, Oct 6
Frontier Logo
7:14 pm - 9:51 amIAD-MDW
15h 37m1 stop
Frontier Logo
6:21 am - 9:19 pmMDW-IAD
13h 58m1 stop
$154Frontier
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
7:14 pm - 9:18 amIAD-MDW
15h 04m1 stop
Frontier Logo
10:51 am - 6:24 pmMDW-IAD
6h 33m1 stop
$155Frontier
Find Deal
Sat, Sep 20 - Sat, Sep 27
Frontier Logo
7:14 pm - 9:51 amIAD-MDW
15h 37m1 stop
Frontier Logo
10:13 am - 6:14 pmMDW-IAD
7h 01m1 stop
$156Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21

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
Sep 11
IAD1:55 pmWashington, D.C. Dulles Intl
10h 25m
1 stop
MDW11:20 pmChicago Midway
Sep 15
MDW5:15 pmChicago Midway
6h 00m
1 stop
IAD12:15 amWashington, D.C. Dulles Intl
$142
Find similar
Frontier
Sep 3
IAD9:30 amWashington, D.C. Dulles Intl
5h 31m
1 stop
MDW2:01 pmChicago Midway
Sep 4
MDW4:56 pmChicago Midway
6h 19m
1 stop
IAD12:15 amWashington, D.C. Dulles Intl
$143
Find similar
Frontier
Sep 5
IAD1:55 pmWashington, D.C. Dulles Intl
10h 25m
1 stop
MDW11:20 pmChicago Midway
Sep 10
MDW9:00 amChicago Midway
9h 55m
1 stop
IAD7:55 pmWashington, D.C. Dulles Intl
$144
Find similar

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 30
IAD1:00 pmWashington, D.C. Dulles Intl
6h 37m
1 stop
MDW6:37 pmChicago Midway
Aug 31
MDW6:00 amChicago Midway
4h 44m
1 stop
IAD11:44 amWashington, D.C. Dulles Intl
$257
Find similar
Delta
Sep 2
IAD6:00 amWashington, D.C. Dulles Intl
4h 36m
1 stop
MDW9:36 amChicago Midway
Sep 16
MDW6:15 pmChicago Midway
3h 51m
1 stop
IAD11:06 pmWashington, D.C. Dulles Intl
$284
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 August 20, 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

Thu 9/11

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 9/15

5:15 pm-12:15 am

1 stop6h 00m

$142

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/5

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 9/8

5:15 pm-12:15 am

1 stop6h 00m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/5

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Wed 9/10

9:00 am-7:55 pm

1 stop9h 55m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Tue 10/14

8:05 am-7:46 pm

1 stop10h 41m

$146

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 9/11

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Sun 9/14

6:21 am-9:19 pm

1 stop13h 58m

$148

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 10/3

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Sun 10/5

6:21 am-9:24 pm

1 stop14h 03m

$149

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/4

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Mon 10/6

5:20 pm-12:15 am

1 stop5h 55m

$150

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/26

7:14 pm-9:51 am

1 stop15h 37m

Chicago Midway

Sun 9/28

6:21 am-9:19 pm

1 stop13h 58m

$154

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/20

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/27

10:51 am-6:24 pm

1 stop6h 33m

$155

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/19

7:14 pm-9:51 am

1 stop15h 37m

Chicago Midway

Sun 9/21

10:13 am-6:14 pm

1 stop7h 01m

$156

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 $319. 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 $390.

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 $318 when looking at flights departing in the evening. Try not to purchase tickets at noon 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.
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. 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 $155Free CancellationRating
5.8
3,207 reviews
Search Frontier flights
DeltaPriceFrom $208Free CancellationRating
7.9
7,982 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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