Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $99

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
7:32 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:42 pm - 12:14 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
16h 32m1 stop Atlanta Hartsfield-Jackson
$208Frontier
Thu, Nov 12 - Thu, Nov 19
Frontier Logo
6:07 pm - 11:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
6h 40m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$208Frontier
Wed, Nov 11 - Thu, Nov 12
Frontier Logo
8:05 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 42m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$209Frontier
Tue, Nov 3 - Wed, Nov 11
Frontier Logo
7:32 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:09 am - 3:03 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
4h 54m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Thu, Nov 19 - Sun, Nov 22
Frontier Logo
7:32 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:09 am - 3:03 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
4h 54m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Thu, Nov 19 - Mon, Nov 23
Frontier Logo
6:07 pm - 11:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
6h 40m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Tue, Nov 10 - Mon, Nov 16
Frontier Logo
7:32 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 15m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$211Frontier
Thu, Nov 12 - Mon, Nov 16
Frontier Logo
6:07 pm - 11:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
6h 40m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:16 am - 3:08 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$212Frontier
Tue, Nov 10 - Fri, Nov 20
Multiple Airlines Logo
6:01 pm - 1:40 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
20h 39m1 stop Knoxville McGhee Tyson
Multiple Airlines Logo
12:28 pm - 11:11 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
21h 43m1 stop Atlanta Hartsfield-Jackson
$219Multiple Airlines
Thu, Nov 19 - Tue, Dec 1
Multiple Airlines Logo
3:35 pm - 8:08 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
5h 33m1 stop Valparaiso Destin-Ft Walton Beach
Multiple Airlines Logo
6:16 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
9h 56m1 stop Atlanta Hartsfield-Jackson
$257Multiple Airlines
Fri, Oct 30 - Mon, Nov 2

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 11
IAD6:07 pmWashington, D.C. Dulles Intl
6h 40m
1 stop
MDW11:47 pmChicago Midway
Nov 12
MDW6:08 amChicago Midway
10h 04m
1 stop
IAD5:12 pmWashington, D.C. Dulles Intl
$208
Frontier
Nov 3
IAD8:05 amWashington, D.C. Dulles Intl
10h 42m
1 stop
MDW5:47 pmChicago Midway
Nov 11
MDW6:08 amChicago Midway
10h 04m
1 stop
IAD5:12 pmWashington, D.C. Dulles Intl
$209
Frontier
Nov 19
IAD7:32 amWashington, D.C. Dulles Intl
11h 15m
1 stop
MDW5:47 pmChicago Midway
Nov 22
MDW9:09 amChicago Midway
4h 54m
1 stop
IAD3:03 pmWashington, D.C. Dulles Intl
$210

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

Thu 11/12

7:32 am-5:47 pm

1 stop11h 15m

Chicago Midway

Thu 11/19

6:42 pm-12:14 pm

1 stop16h 32m

$208

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Wed 11/11

6:07 pm-11:47 pm

1 stop6h 40m

Chicago Midway

Thu 11/12

6:08 am-5:12 pm

1 stop10h 04m

$208

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Tue 11/3

8:05 am-5:47 pm

1 stop10h 42m

Chicago Midway

Wed 11/11

6:08 am-5:12 pm

1 stop10h 04m

$209

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Thu 11/19

7:32 am-5:47 pm

1 stop11h 15m

Chicago Midway

Sun 11/22

9:09 am-3:03 pm

1 stop4h 54m

$210

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Thu 11/19

7:32 am-5:47 pm

1 stop11h 15m

Chicago Midway

Mon 11/23

9:09 am-3:03 pm

1 stop4h 54m

$210

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Tue 11/10

6:07 pm-11:47 pm

1 stop6h 40m

Chicago Midway

Mon 11/16

6:08 am-5:12 pm

1 stop10h 04m

$210

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Thu 11/12

7:32 am-5:47 pm

1 stop11h 15m

Chicago Midway

Mon 11/16

6:08 am-5:12 pm

1 stop10h 04m

$211
Quickest round-trip

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Tue 11/10

6:07 pm-11:47 pm

1 stop6h 40m

Chicago Midway

Fri 11/20

8:16 am-3:08 pm

1 stop5h 52m

$212

Washington, D.C.Chicago

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

IADMDW

Washington, D.C. Dulles Intl

Thu 11/19

6:01 pm-1:40 pm

1 stop20h 39m

Chicago Midway

Tue 12/1

12:28 pm-11:11 am

1 stop21h 43m

$219

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

Mon 11/2

6:16 am-5:12 pm

1 stop9h 56m

$257

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $348. 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 $435.

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 $342 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $400. 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

$99

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 $99. 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 $208.
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 $70Free CancellationRating
5.5
2,538 reviews
Search Frontier flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Saint Joseph
Lansing
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

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.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/14
Sat 11/21
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago