What is the cheapest airline that flies from Washington, D.C. Dulles Intl to Chicago Midway?

Frontier and Delta are the most popular carriers operating from Washington, D.C. Dulles Intl to Chicago Midway

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

As of August 2026, there are 2 operators available to choose from for flights 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.

$96 Cheap Flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:50 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 28m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Sat, Oct 3 - Mon, Oct 5

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Wed, Sep 23 - Thu, Sep 24

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Wed, Sep 30 - Tue, Oct 6

7:50 am - 5:46 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

10h 56m1 stop Atlanta Hartsfield-Jackson

6:21 am - 5:13 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 52m1 stop Atlanta Hartsfield-Jackson

$179Frontier

Tue, Oct 6 - Tue, Oct 20

6:05 am - 9:17 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

4h 12m1 stop Detroit Metropolitan Wayne County

6:44 pm - 11:16 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

3h 32m1 stop Detroit Metropolitan Wayne County

$197Delta

Wed, Oct 28 - Sat, Oct 31

6:10 am - 9:07 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

5:06 pm - 12:41 amMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

6h 35m1 stop Atlanta Hartsfield-Jackson

$197Delta

Thu, Oct 1 - Mon, Oct 5

6:12 pm - 10:33 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 21m1 stop Atlanta Hartsfield-Jackson

6:44 pm - 11:16 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

3h 32m1 stop Detroit Metropolitan Wayne County

$197Delta

Sat, Oct 17 - Mon, Oct 19

3:35 pm - 8:08 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 33m1 stop Valparaiso Destin-Ft Walton Beach

6:16 am - 5:12 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 56m1 stop Atlanta Hartsfield-Jackson

$328Multiple Airlines

Fri, Oct 30 - Tue, Nov 3

3:35 pm - 8:08 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 33m1 stop Valparaiso Destin-Ft Walton Beach

7:25 am - 8:11 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

11h 46m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$347Multiple Airlines

Fri, Oct 30 - Sat, Oct 31

11:12 am - 11:43 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

13h 31m2 stops Orlando Atlanta Hartsfield-Jackson

11:38 am - 6:45 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

6h 07m1 stop Punta Gorda

$401Multiple Airlines

Tue, Oct 13 - Sun, Oct 18

Cheap last minute flights

Enter your travel dates to find the best prices.

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$270Frontier

Tue, Sep 1 - Wed, Sep 9

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$270Frontier

Wed, Sep 2 - Wed, Sep 9

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

11:50 am - 10:52 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

10h 02m1 stop Atlanta Hartsfield-Jackson

$270Frontier

Tue, Sep 1 - Tue, Sep 8

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

11:50 am - 10:52 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

10h 02m1 stop Atlanta Hartsfield-Jackson

$270Frontier

Wed, Sep 2 - Tue, Sep 8

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:05 am - 5:14 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

10h 09m1 stop Atlanta Hartsfield-Jackson

$290Frontier

Tue, Sep 1 - Sun, Sep 6

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$290Frontier

Fri, Sep 4 - Mon, Sep 14

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:05 am - 5:14 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

10h 09m1 stop Atlanta Hartsfield-Jackson

$292Frontier

Tue, Sep 1 - Sat, Sep 5

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$297Frontier

Mon, Aug 31 - Wed, Sep 9

5:42 pm - 10:36 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 54m1 stop Atlanta Hartsfield-Jackson

9:24 am - 4:38 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

6h 14m1 stop Detroit Metropolitan Wayne County

$459Delta

Fri, Sep 4 - Sun, Sep 6

5:42 pm - 10:36 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 54m1 stop Atlanta Hartsfield-Jackson

5:45 pm - 11:26 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

4h 41m1 stop Detroit Metropolitan Wayne County

$459Delta

Fri, Sep 4 - Sat, Sep 5

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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

Sep 23

IAD7:50 amWashington, D.C. Dulles Intl

11h 01m

1 stop

MDW5:51 pmChicago Midway

Sep 24

MDW6:25 amChicago Midway

9h 53m

1 stop

IAD5:18 pmWashington, D.C. Dulles Intl

$177

Frontier

Oct 6

IAD7:50 amWashington, D.C. Dulles Intl

10h 56m

1 stop

MDW5:46 pmChicago Midway

Oct 20

MDW6:21 amChicago Midway

9h 52m

1 stop

IAD5:13 pmWashington, D.C. Dulles Intl

$179

Frontier

Sep 22

IAD7:50 amWashington, D.C. Dulles Intl

10h 56m

1 stop

MDW5:46 pmChicago Midway

Sep 23

MDW6:25 amChicago Midway

9h 53m

1 stop

IAD5:18 pmWashington, D.C. Dulles Intl

$180

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

Oct 14

IAD6:05 amWashington, D.C. Dulles Intl

4h 12m

1 stop

MDW9:17 amChicago Midway

Oct 17

MDW6:44 pmChicago Midway

3h 32m

1 stop

IAD11:16 pmWashington, D.C. Dulles Intl

$197

Delta

Oct 6

IAD6:05 amWashington, D.C. Dulles Intl

4h 12m

1 stop

MDW9:17 amChicago Midway

Oct 9

MDW6:44 pmChicago Midway

3h 32m

1 stop

IAD11:16 pmWashington, D.C. Dulles Intl

$236

momondo Fare Finder

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 Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sat 10/3

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Mon 10/5

6:50 am-5:18 pm

1 stop9h 28m

$177

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Wed 9/23

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Thu 9/24

6:25 am-5:18 pm

1 stop9h 53m

$177

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Wed 9/30

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Tue 10/6

6:25 am-5:18 pm

1 stop9h 53m

$177

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 10/6

7:50 am-5:46 pm

1 stop10h 56m

Chicago Midway

Tue 10/20

6:21 am-5:13 pm

1 stop9h 52m

$179

Quickest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Wed 10/28

6:05 am-9:17 am

1 stop4h 12m

Chicago Midway

Sat 10/31

6:44 pm-11:16 pm

1 stop3h 32m

$197

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Thu 10/1

6:10 am-9:07 am

1 stop3h 57m

Chicago Midway

Mon 10/5

5:06 pm-12:41 am

1 stop6h 35m

$197

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sat 10/17

6:12 pm-10:33 pm

1 stop5h 21m

Chicago Midway

Mon 10/19

6:44 pm-11:16 pm

1 stop3h 32m

$197

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Fri 10/30

3:35 pm-8:08 pm

1 stop5h 33m

Chicago Midway

Tue 11/3

6:16 am-5:12 pm

1 stop9h 56m

$328

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Fri 10/30

3:35 pm-8:08 pm

1 stop5h 33m

Chicago Midway

Sat 10/31

7:25 am-8:11 pm

2 stops11h 46m

$347

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 10/13

11:12 am-11:43 pm

2 stops13h 31m

Chicago Midway

Sun 10/18

11:38 am-6:45 pm

1 stop6h 07m

$401

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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

Prices are currently typical for flights on this route.

Typical prices usually range from $169 to $203.
The lowest price recently found on this route was $177.

What is the cheapest month to fly to Chicago Midway Airport?

The month of July 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 July, then departing from Washington, D.C. Dulles Intl Airport during the month January is also very affordable. Most momondo users find prices during this month for around $0.

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 $341. 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 $426.

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 $314 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $387. 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

Best Price Found	$96
Fastest flight time	3h 35m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Washington, D.C. Dulles Intl Airport in the past 72 hours is $96. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $177.

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?
As of August 2026, there are 2 operators available to choose from 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?
momondo data reveals that the most frequently booked airline on the route from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport is Frontier, representing 52% of all bookings. The subsequent popular airline is Delta at 48%.

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
Frontier	PriceFrom $70	Free Cancellation	Rating 5.6 2,637 reviews		Search Frontier flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.8 8,541 reviews		Search Delta flights

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Schererville

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Porter

Crown Point

Griffith

Saint John

Why use momondo?

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

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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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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $96

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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

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

momondo Fare Finder

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.

See travel insights to Chicago from

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

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 month to fly to Chicago Midway Airport?

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

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

What is the cheapest airline that flies from Washington, D.C. Dulles Intl to Chicago Midway?

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

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

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Popular flights according to clicks in the last 7 days on momondo

Washington, D.C. Dulles Intl Airport flight routes

According to popular flight searches on momondo this year

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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