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Cheap flights from Washington, D.C. 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. to Chicago departing on 7/21. 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. to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:55 am - 1:30 pm
BWI
-
MDW
3h 35m
1 stop
Southwest Logo
6:35 am - 2:20 pm
MDW
-
BWI
6h 45m
1 stop
$226Southwest
Wed, Aug 5 - Sat, Aug 8
Southwest Logo
9:25 pm - 10:25 pm
BWI
-
MDW
2h 00mnonstop
Southwest Logo
7:25 am - 10:15 am
MDW
-
BWI
1h 50mnonstop
$227Southwest
Sat, Jun 13 - Wed, Jun 17
Southwest Logo
9:25 pm - 10:30 pm
BWI
-
MDW
2h 05mnonstop
Southwest Logo
8:10 am - 11:10 am
MDW
-
BWI
2h 00mnonstop
$229Southwest
Sat, Jul 11 - Tue, Jul 14
Southwest Logo
1:00 pm - 4:10 pm
BWI
-
MDW
4h 10m
1 stop
Southwest Logo
7:35 pm - 10:25 pm
MDW
-
BWI
1h 50mnonstop
$231Southwest
Wed, Jul 1 - Wed, Jul 1
Southwest Logo
9:25 pm - 10:25 pm
BWI
-
MDW
2h 00mnonstop
Southwest Logo
7:50 am - 1:00 pm
MDW
-
BWI
4h 10m
1 stop
$233Southwest
Sat, Jun 13 - Wed, Jun 17
Delta Logo
8:28 am - 11:51 am
IAD
-
MDW
4h 23m
1 stop
Delta Logo
6:42 pm - 11:26 pm
MDW
-
IAD
3h 44m
1 stop
$238Delta
Tue, Aug 18 - Thu, Aug 20
Delta Logo
6:00 am - 9:53 am
DCA
-
MDW
4h 53m
1 stop
Delta Logo
5:10 pm - 11:43 pm
MDW
-
DCA
5h 33m
1 stop
$238Delta
Wed, Sep 16 - Mon, Sep 21
Frontier Logo
11:24 am - 10:11 pm
IAD
-
MDW
11h 47m
1 stop
Frontier Logo
12:04 pm - 11:17 pm
MDW
-
IAD
10h 13m
1 stop
$240Frontier
Tue, Jun 16 - Mon, Jun 22
Frontier Logo
11:24 am - 10:11 pm
IAD
-
MDW
11h 47m
1 stop
Frontier Logo
11:59 am - 11:17 pm
MDW
-
IAD
10h 18m
1 stop
$241Frontier
Tue, Jun 23 - Sat, Jun 27
Multiple Airlines Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Multiple Airlines Logo
2:48 pm - 2:26 pm
MDW
-
IAD
22h 38m
1 stop
$256Multiple Airlines
Wed, Jul 1 - Sun, Jul 5

Frontier flights from Washington, D.C. to Chicago Midway Airport

Our best Frontier deals on Washington, D.C. to Chicago Midway Airport flight tickets
Frontier
Jun 16
IAD11:24 amWashington, D.C. Dulles Intl
11h 47m
1 stop
MDW10:11 pmChicago Midway
Jun 22
MDW12:04 pmChicago Midway
10h 13m
1 stop
IAD11:17 pmWashington, D.C. Dulles Intl
$240
Frontier
Jun 23
IAD11:24 amWashington, D.C. Dulles Intl
11h 47m
1 stop
MDW10:11 pmChicago Midway
Jun 27
MDW11:59 amChicago Midway
10h 18m
1 stop
IAD11:17 pmWashington, D.C. Dulles Intl
$241
Frontier
Jun 24
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
Jul 4
MDW11:59 amChicago Midway
10h 18m
1 stop
IAD11:17 pmWashington, D.C. Dulles Intl
$244

Delta flights from Washington, D.C. to Chicago Midway Airport

Our best Delta deals on Washington, D.C. to Chicago Midway Airport flight tickets
Delta
Sep 16
DCA6:00 amWashington, D.C. Reagan-National
4h 53m
1 stop
MDW9:53 amChicago Midway
Sep 21
MDW5:10 pmChicago Midway
5h 33m
1 stop
DCA11:43 pmWashington, D.C. Reagan-National
$238
Delta
Jul 1
DCA6:00 amWashington, D.C. Reagan-National
4h 14m
1 stop
MDW9:14 amChicago Midway
Jul 7
MDW1:18 pmChicago Midway
4h 41m
1 stop
DCA6:59 pmWashington, D.C. Reagan-National
$248
Delta
Jul 22
BWI11:52 amBaltimore/Washington
5h 22m
1 stop
MDW4:14 pmChicago Midway
Jul 25
MDW6:35 pmChicago Midway
3h 43m
1 stop
BWI11:18 pmBaltimore/Washington
$249

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. 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 May 28, 2026.
Use the filters below to find and compare flights from Washington, D.C. to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 8/5

10:55 am-1:30 pm

1 stop3h 35m

Chicago Midway

Sat 8/8

6:35 am-2:20 pm

1 stop6h 45m

$226
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 6/13

9:25 pm-10:25 pm

Nonstop2h 00m

Chicago Midway

Wed 6/17

7:25 am-10:15 am

Nonstop1h 50m

$227

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 7/11

9:25 pm-10:30 pm

Nonstop2h 05m

Chicago Midway

Tue 7/14

8:10 am-11:10 am

Nonstop2h 00m

$229

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 7/1

1:00 pm-4:10 pm

1 stop4h 10m

Chicago Midway

Wed 7/1

7:35 pm-10:25 pm

Nonstop1h 50m

$231

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 6/13

9:25 pm-10:25 pm

Nonstop2h 00m

Chicago Midway

Wed 6/17

7:50 am-1:00 pm

1 stop4h 10m

$233

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/18

8:28 am-11:51 am

1 stop4h 23m

Chicago Midway

Thu 8/20

6:42 pm-11:26 pm

1 stop3h 44m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/16

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

Mon 9/21

5:10 pm-11:43 pm

1 stop5h 33m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/16

11:24 am-10:11 pm

1 stop11h 47m

Chicago Midway

Mon 6/22

12:04 pm-11:17 pm

1 stop10h 13m

$240

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/23

11:24 am-10:11 pm

1 stop11h 47m

Chicago Midway

Sat 6/27

11:59 am-11:17 pm

1 stop10h 18m

$241

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 7/1

11:17 am-10:11 pm

1 stop11h 54m

Chicago Midway

Sun 7/5

2:48 pm-2:26 pm

1 stop22h 38m

$256

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. 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 typical price of a round-trip flight between Washington, D.C. and Chicago Midway Airport?

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

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C., with most prices found around $70. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Washington, D.C. during the month September is also very affordable. Most momondo users find prices during this month for around $77.

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.. The lowest ticket price found for a Saturday departure recently was $336. 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. because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $405.

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. at noon is the least expensive time of day to depart. momondo users have found prices as low as $327 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $373. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Washington, D.C. to Chicago Midway flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago Midway flight prices

What cabin class options are available on Washington, D.C. to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Washington, D.C. to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago Midway Airport.

How have Washington, D.C. to Chicago Midway Airport flight prices changed over time?

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

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. 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. to Chicago Midway Airport (WAS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago Midway Airport

Best Price Found

$183

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Washington, D.C. in the past 72 hours is $183. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $320.
The fastest flight from Washington, D.C. to Chicago Midway Airport takes 1h 55m
Direct flights go from Washington, D.C. to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Washington, D.C. to Chicago Midway Airport

  • How far is Washington, D.C. to Chicago Midway by plane?

    Washington, D.C. and Chicago Midway are 597.2 mi apart from one another. In terms of flight time, this usually takes a little over 1h 55m.

  • When did momondo last update prices for flights from Washington, D.C. to Chicago Midway Airport?

    Prices for flights from Washington, D.C. to Chicago Midway Airport are updated daily.

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

  • How old do you have to be to fly from Washington, D.C. to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Washington, D.C. to Chicago Midway Airport?

  • What is the most popular airline from Washington, D.C. to Chicago Midway Airport?

Best airlines flying from Washington, D.C. to Chicago Midway Airport

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $90Free CancellationRating
5.6
2,930 reviews
Search Frontier flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,422 reviews
Search Delta flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,265 reviews
Search Southwest flights

  • Southwest Flights From Washington, D.C. to Chicago Midway Airport

    The lowest priced Southwest flight from Washington, D.C. to Chicago Midway Airport from the last 72 hours was $158. Generally, Southwest has 33 flights on this route every week with an average price of $328. Southwest is rated 7.9/10 by our users.

Traveling to a place near Chicago?

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

Yes. momondo enables you to select and highlight flights to Chicago from Washington, D.C. with this policy.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Washington, D.C..

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

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