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Cheap flights from Washington, D.C. to Chicago from $64

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 2/3. 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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0 bags

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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.
Frontier Logo
7:10 am - 12:05 pm
BWI
-
MDW
5h 55m
1 stop
Frontier Logo
6:15 am - 5:47 pm
MDW
-
BWI
10h 32m
1 stop
$128Frontier
Wed, Feb 4 - Wed, Feb 11
Frontier Logo
8:25 pm - 2:26 pm
BWI
-
MDW
19h 01m
1 stop
Frontier Logo
7:15 am - 5:47 pm
MDW
-
BWI
9h 32m
1 stop
$138Frontier
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
10:20 am - 11:30 am
BWI
-
MDW
2h 10mnonstop
Southwest Logo
6:15 pm - 9:05 pm
MDW
-
BWI
1h 50mnonstop
$139Southwest
Thu, Feb 12 - Sat, Feb 14
Frontier Logo
7:10 am - 12:05 pm
BWI
-
MDW
5h 55m
1 stop
Frontier Logo
5:01 pm - 12:36 am
MDW
-
BWI
6h 35m
1 stop
$140Frontier
Tue, Feb 3 - Thu, Feb 5
Frontier Logo
10:29 am - 9:33 pm
IAD
-
MDW
12h 04m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$143Frontier
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
11:24 am - 10:19 pm
BWI
-
MDW
11h 55m
1 stop
Frontier Logo
1:20 pm - 12:21 am
MDW
-
BWI
10h 01m
1 stop
$144Frontier
Mon, Feb 2 - Tue, Feb 3
Frontier Logo
5:37 pm - 10:37 pm
IAD
-
MDW
6h 00m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$150Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
6:00 am - 11:45 am
BWI
-
MDW
6h 45m
1 stop
Frontier Logo
1:20 pm - 12:21 am
MDW
-
BWI
10h 01m
1 stop
$150Frontier
Mon, Jan 26 - Tue, Jan 27
Frontier Logo
5:37 pm - 10:19 pm
IAD
-
MDW
5h 42m
1 stop
Frontier Logo
6:20 am - 4:28 pm
MDW
-
IAD
9h 08m
1 stop
$151Frontier
Thu, Feb 5 - Mon, Feb 9
Southwest Logo
6:05 am - 7:20 am
DCA
-
MDW
2h 15mnonstop
Southwest Logo
5:25 pm - 8:15 pm
MDW
-
DCA
1h 50mnonstop
$211Southwest
Sat, Feb 7 - Tue, Feb 10

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
Feb 19
BWI6:00 amBaltimore/Washington
6h 27m
1 stop
MDW11:27 amChicago Midway
Feb 23
MDW2:19 pmChicago Midway
25h 54m
1 stop
BWI5:13 pmBaltimore/Washington
$127
Frontier
Feb 4
BWI7:10 amBaltimore/Washington
5h 55m
1 stop
MDW12:05 pmChicago Midway
Feb 11
MDW6:15 amChicago Midway
10h 32m
1 stop
BWI5:47 pmBaltimore/Washington
$128
Frontier
Feb 3
BWI7:10 amBaltimore/Washington
5h 55m
1 stop
MDW12:05 pmChicago Midway
Feb 5
MDW5:01 pmChicago Midway
6h 35m
1 stop
BWI12:36 amBaltimore/Washington
$140

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
Feb 12
BWI10:20 amBaltimore/Washington
2h 10m
MDW11:30 amChicago Midway
Feb 14
MDW6:15 pmChicago Midway
1h 50m
BWI9:05 pmBaltimore/Washington
$139
Southwest
Feb 13
BWI9:35 pmBaltimore/Washington
2h 10m
MDW10:45 pmChicago Midway
Feb 17
MDW7:05 pmChicago Midway
1h 50m
BWI9:55 pmBaltimore/Washington
$158
Southwest
Feb 3
BWI5:50 pmBaltimore/Washington
2h 10m
MDW7:00 pmChicago Midway
Feb 5
MDW7:05 pmChicago Midway
1h 50m
BWI9:55 pmBaltimore/Washington
$159

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 January 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

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 2/4

7:10 am-12:05 pm

1 stop5h 55m

Chicago Midway

Wed 2/11

6:15 am-5:47 pm

1 stop10h 32m

$128

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 2/25

8:25 pm-2:26 pm

1 stop19h 01m

Chicago Midway

Wed 3/4

7:15 am-5:47 pm

1 stop9h 32m

$138

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/12

10:20 am-11:30 am

Nonstop2h 10m

Chicago Midway

Sat 2/14

6:15 pm-9:05 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 2/3

7:10 am-12:05 pm

1 stop5h 55m

Chicago Midway

Thu 2/5

5:01 pm-12:36 am

1 stop6h 35m

$140

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$143

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 2/2

11:24 am-10:19 pm

1 stop11h 55m

Chicago Midway

Tue 2/3

1:20 pm-12:21 am

1 stop10h 01m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/19

5:37 pm-10:37 pm

1 stop6h 00m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$150

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 1/26

6:00 am-11:45 am

1 stop6h 45m

Chicago Midway

Tue 1/27

1:20 pm-12:21 am

1 stop10h 01m

$150

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/5

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Mon 2/9

6:20 am-4:28 pm

1 stop9h 08m

$151

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/7

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Tue 2/10

5:25 pm-8:15 pm

Nonstop1h 50m

$211

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 cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C., with most prices found around $187. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Washington, D.C. during the month August is also very affordable. Most momondo users find prices during this month for around $202.

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.. The lowest ticket price found for a Wednesday departure recently was $305. 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 $376.

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. in the evening is the least expensive time of day to depart. momondo users have found prices as low as $297 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $351. 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 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?

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

$125

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 $125. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $250.
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

  • 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 $63Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,257 reviews
Search Southwest flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,039 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 $158. Generally, Southwest has 24 flights on this route every week with an average price of $299. 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
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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