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Cheap flights from Washington, D.C. to Chicago from $89

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 5/19. 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
5:10 pm - 6:15 pm
BWI
-
MDW
2h 05mnonstop
Southwest Logo
5:00 pm - 7:50 pm
MDW
-
BWI
1h 50mnonstop
$198Southwest
Sat, May 2 - Wed, May 6
Frontier Logo
12:18 pm - 6:37 pm
BWI
-
MDW
7h 19m
1 stop
Frontier Logo
2:15 pm - 12:44 am
MDW
-
BWI
9h 29m
1 stop
$199Frontier
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
7:30 pm - 8:40 pm
BWI
-
MDW
2h 10mnonstop
Southwest Logo
9:25 pm - 12:15 am
MDW
-
BWI
1h 50mnonstop
$200Southwest
Sat, May 2 - Mon, May 4
Frontier Logo
6:45 am - 11:09 am
BWI
-
MDW
5h 24m
1 stop
Frontier Logo
6:00 am - 6:28 pm
MDW
-
BWI
11h 28m
1 stop
$201Frontier
Wed, Jun 3 - Fri, Jun 5
Frontier Logo
12:27 pm - 10:19 pm
BWI
-
MDW
10h 52m
1 stop
Frontier Logo
6:00 am - 5:11 pm
MDW
-
BWI
10h 11m
1 stop
$202Frontier
Mon, Apr 27 - Thu, Apr 30
Frontier Logo
4:25 pm - 10:26 pm
BWI
-
MDW
7h 01m
1 stop
Frontier Logo
6:00 am - 1:48 pm
MDW
-
BWI
6h 48m
1 stop
$203Frontier
Fri, May 1 - Mon, May 4
Southwest Logo
4:50 pm - 7:35 pm
BWI
-
MDW
3h 45m
1 stop
Southwest Logo
12:05 pm - 2:55 pm
MDW
-
BWI
1h 50mnonstop
$204Southwest
Tue, May 12 - Sat, May 16
Frontier Logo
6:45 am - 11:09 am
BWI
-
MDW
5h 24m
1 stop
Frontier Logo
12:19 pm - 6:22 pm
MDW
-
BWI
5h 03m
1 stop
$205Frontier
Thu, May 7 - Thu, May 14
Delta Logo
6:05 am - 8:43 am
DCA
-
MDW
3h 38m
1 stop
Delta Logo
6:36 pm - 10:59 pm
MDW
-
DCA
3h 23m
1 stop
$227Delta
Thu, May 7 - Wed, May 20
Delta Logo
12:37 pm - 4:26 pm
IAD
-
MDW
4h 49m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
Tue, May 5 - Sat, May 9

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

Our best Southwest deals on Washington, D.C. to Chicago Midway Airport flight tickets
Southwest
May 2
BWI7:30 pmBaltimore/Washington
2h 10m
MDW8:40 pmChicago Midway
May 4
MDW9:25 pmChicago Midway
1h 50m
BWI12:15 amBaltimore/Washington
$200
Southwest
May 23
BWI7:30 pmBaltimore/Washington
2h 10m
MDW8:40 pmChicago Midway
May 27
MDW7:50 amChicago Midway
3h 20m
1 stop
BWI12:10 pmBaltimore/Washington
$204
Southwest
May 20
BWI4:50 pmBaltimore/Washington
3h 45m
1 stop
MDW7:35 pmChicago Midway
May 27
MDW5:00 pmChicago Midway
1h 50m
BWI7:50 pmBaltimore/Washington
$206

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
May 7
DCA6:05 amWashington, D.C. Reagan-National
3h 38m
1 stop
MDW8:43 amChicago Midway
May 20
MDW6:36 pmChicago Midway
3h 23m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$227
Delta
May 5
IAD12:37 pmWashington, D.C. Dulles Intl
4h 49m
1 stop
MDW4:26 pmChicago Midway
May 9
MDW6:36 pmChicago Midway
3h 20m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$228
Delta
May 5
IAD5:27 pmWashington, D.C. Dulles Intl
6h 01m
1 stop
MDW10:28 pmChicago Midway
May 9
MDW5:29 pmChicago Midway
6h 22m
1 stop
IAD12:51 amWashington, D.C. Dulles Intl
$238

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 April 13, 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
Quickest round-trip

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 5/2

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Wed 5/6

5:00 pm-7:50 pm

Nonstop1h 50m

$198

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 4/25

12:18 pm-6:37 pm

1 stop7h 19m

Chicago Midway

Tue 4/28

2:15 pm-12:44 am

1 stop9h 29m

$199

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 5/2

7:30 pm-8:40 pm

Nonstop2h 10m

Chicago Midway

Mon 5/4

9:25 pm-12:15 am

Nonstop1h 50m

$200

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 6/3

6:45 am-11:09 am

1 stop5h 24m

Chicago Midway

Fri 6/5

6:00 am-6:28 pm

1 stop11h 28m

$201

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 4/27

12:27 pm-10:19 pm

1 stop10h 52m

Chicago Midway

Thu 4/30

6:00 am-5:11 pm

1 stop10h 11m

$202

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 5/1

4:25 pm-10:26 pm

1 stop7h 01m

Chicago Midway

Mon 5/4

6:00 am-1:48 pm

1 stop6h 48m

$203

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 5/12

4:50 pm-7:35 pm

1 stop3h 45m

Chicago Midway

Sat 5/16

12:05 pm-2:55 pm

Nonstop1h 50m

$204

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 5/7

6:45 am-11:09 am

1 stop5h 24m

Chicago Midway

Thu 5/14

12:19 pm-6:22 pm

1 stop5h 03m

$205

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/7

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Wed 5/20

6:36 pm-10:59 pm

1 stop3h 23m

$227

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 5/5

12:37 pm-4:26 pm

1 stop4h 49m

Chicago Midway

Sat 5/9

6:36 pm-10:56 pm

1 stop3h 20m

$228

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C., with most prices found around $207. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Washington, D.C. during the month September is also very affordable. Most momondo users find prices during this month for around $228.

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 $328. 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 $384.

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 $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $364. 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 Washington, D.C. Reagan-National 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 flights?

There is only 1 cabin class available to choose from on Washington, D.C. to Chicago Midway 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?

You could potentially save up to 6% on your flight if you consider stops on a Washington, D.C. to Chicago Midway Airport flight.

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

$189

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 $189. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $296.
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 $95Free CancellationRating
5.7
2,993 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,331 reviews
Search Southwest flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,406 reviews
Search Delta 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 $159. Generally, Southwest has 34 flights on this route every week with an average price of $300. Southwest is rated 8.0/10 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
Chesterton
Monticello
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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