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Cheap flights from Washington, D.C. to Chicago Midway Airport from $34

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 Midway Airport departing on 2/19. 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

These are some of the best round-trip flight deals from Washington, D.C. to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Washington, D.C. to Chicago.

Cheap last minute flights

Planning a quick getaway from Washington, D.C. to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Washington, D.C. to Chicago

Find recent round-trip train or bus tickets from Washington, D.C. to Chicago.

All round-trip flight deals from Washington, D.C. to Chicago

The cheapest plane tickets from Washington, D.C. to Chicago found on KAYAK recently.
4:45 pm - 5:51 pmBWI-MDW
2h 06mnonstop
1:05 pm - 3:55 pmMDW-BWI
1h 50mnonstop
$57Frontier
Find Deal
Wed, Apr 2 - Wed, Apr 9
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$62Frontier
Find Deal
Mon, Mar 3 - Wed, Mar 5
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$68Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$70Frontier
Find Deal
Sat, Feb 22 - Mon, Feb 24
8:50 pm - 10:00 pmBWI-MDW
2h 10mnonstop
6:55 pm - 9:45 pmMDW-BWI
1h 50mnonstop
$137Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
5:00 pm - 6:10 pmBWI-MDW
2h 10mnonstop
6:10 pm - 9:00 pmMDW-BWI
1h 50mnonstop
$177Southwest
Find Deal
Fri, Feb 28 - Mon, Mar 3
6:00 am - 8:43 amIAD-MDW
3h 43m1 stop
6:00 am - 11:24 amMDW-IAD
4h 24m1 stop
$197Delta
Find Deal
Wed, Apr 9 - Tue, Apr 22
10:20 am - 4:20 pmBWI-MDW
7h 00m1 stop
10:57 am - 5:36 pmMDW-BWI
5h 39m1 stop
$197Delta
Find Deal
Tue, Feb 18 - Thu, Feb 20
9:10 pm - 2:03 pmIAD-MDW
17h 53m2 stops
8:05 am - 9:09 pmMDW-IAD
12h 04m3 stops
Thu, Jun 5 - Mon, Jun 9
12:40 pm - 9:41 amIAD-MDW
22h 01m2 stops
11:37 am - 11:20 amMDW-IAD
22h 43m3 stops
Thu, Jul 10 - Sun, Jul 13
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
$34Frontier
Find Deal
Wed, Feb 19
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
$38Frontier
Find Deal
Mon, Feb 24
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
$39Frontier
Find Deal
Sat, Feb 15
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
$40Frontier
Find Deal
Sat, Mar 1
8:10 pm - 9:25 pmBWI-MDW
2h 15mnonstop
$69Southwest
Find Deal
Tue, Feb 25
12:35 pm - 1:40 pmBWI-MDW
2h 05mnonstop
$70Southwest
Find Deal
Tue, Mar 25
6:00 am - 10:12 amIAD-MDW
5h 12m1 stop
$99Delta
Find Deal
Thu, Feb 13
12:26 pm - 6:11 pmBWI-MDW
6h 45m1 stop
$99Delta
Find Deal
Tue, Feb 18
5:40 pm - 5:46 pmIAD-MDW
25h 06m3 stops
Mon, Mar 17
5:40 pm - 5:46 pmIAD-MDW
25h 06m3 stops
Mon, Mar 10
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
4:58 pm - 12:17 amMDW-BWI
6h 19m1 stop
$209Frontier
Find Deal
Sat, Jan 25 - Tue, Mar 25
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$210Frontier
Find Deal
Sat, Jan 25 - Wed, Mar 26
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
7:50 am - 7:03 pmMDW-BWI
10h 13m1 stop
$229Frontier
Find Deal
Sat, Jan 25 - Wed, Mar 26
6:35 pm - 11:29 pmBWI-MDW
5h 54m1 stop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$237Frontier
Find Deal
Sat, Jan 25 - Mon, Mar 24
4:00 pm - 5:05 pmDCA-MDW
2h 05mnonstop
5:25 pm - 8:10 pmMDW-DCA
1h 45mnonstop
$439Southwest
Find Deal
Sat, Jan 25 - Mon, Mar 24
7:55 am - 3:10 pmDCA-MDW
8h 15m1 stop
5:25 pm - 8:10 pmMDW-DCA
1h 45mnonstop
$449Southwest
Find Deal
Sat, Jan 25 - Mon, Mar 24
11:00 am - 5:50 pmDCA-MDW
7h 50m2 stops
5:25 pm - 8:10 pmMDW-DCA
1h 45mnonstop
$454Southwest
Find Deal
Sat, Jan 25 - Mon, Mar 24
6:00 am - 10:12 amIAD-MDW
5h 12m1 stop
6:42 pm - 11:00 pmMDW-IAD
3h 18m1 stop
$494Delta
Find Deal
Sat, Jan 25 - Mon, Mar 24
6:05 am - 10:36 amDCA-MDW
5h 31m1 stop
6:42 pm - 11:16 pmMDW-DCA
3h 34m1 stop
$494Delta
Find Deal
Sat, Jan 25 - Wed, Mar 26
6:00 am - 10:12 amIAD-MDW
5h 12m1 stop
6:28 pm - 11:16 pmMDW-IAD
3h 48m1 stop
$549Delta
Find Deal
Sun, Jan 26 - Wed, Jan 29
4:45 pm - 5:51 pmBWI-MDW
2h 06mnonstop
1:05 pm - 3:55 pmMDW-BWI
1h 50mnonstop
$57Frontier
Find Deal
Wed, Apr 2 - Wed, Apr 9
4:21 pm - 5:33 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$62Frontier
Find Deal
Mon, Mar 3 - Wed, Mar 5
7:53 pm - 9:05 pmBWI-MDW
2h 12mnonstop
1:16 pm - 4:11 pmMDW-BWI
1h 55mnonstop
$68Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$70Frontier
Find Deal
Sat, Feb 22 - Mon, Feb 24
4:45 pm - 5:51 pmBWI-MDW
2h 06mnonstop
1:05 pm - 3:55 pmMDW-BWI
1h 50mnonstop
$77Frontier
Find Deal
Wed, Apr 9 - Wed, Apr 16
5:11 pm - 6:23 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$78Frontier
Find Deal
Wed, Feb 12 - Sat, Feb 15
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
10:26 am - 1:21 pmMDW-BWI
1h 55mnonstop
$80Frontier
Find Deal
Sat, Feb 15 - Sat, Feb 22
2:21 pm - 3:33 pmBWI-MDW
2h 12mnonstop
12:26 pm - 3:21 pmMDW-BWI
1h 55mnonstop
$83Frontier
Find Deal
Sat, Feb 22 - Mon, Feb 24
8:50 pm - 10:00 pmBWI-MDW
2h 10mnonstop
6:55 pm - 9:45 pmMDW-BWI
1h 50mnonstop
$137Southwest
Find Deal
Tue, Feb 18 - Tue, Feb 25
5:00 pm - 6:10 pmBWI-MDW
2h 10mnonstop
6:10 pm - 9:00 pmMDW-BWI
1h 50mnonstop
$177Southwest
Find Deal
Fri, Feb 28 - Mon, Mar 3

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
Apr 2
BWI4:45 pmBaltimore/Washington
2h 06m
MDW5:51 pmChicago Midway
Apr 9
MDW1:05 pmChicago Midway
1h 50m
BWI3:55 pmBaltimore/Washington
Frontier
Mar 3
BWI4:21 pmBaltimore/Washington
2h 12m
MDW5:33 pmChicago Midway
Mar 5
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington
Frontier
Feb 10
BWI7:53 pmBaltimore/Washington
2h 12m
MDW9:05 pmChicago Midway
Feb 12
MDW1:16 pmChicago Midway
1h 55m
BWI4:11 pmBaltimore/Washington

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 18
BWI8:50 pmBaltimore/Washington
2h 10m
MDW10:00 pmChicago Midway
Feb 25
MDW6:55 pmChicago Midway
1h 50m
BWI9:45 pmBaltimore/Washington
Southwest
Feb 28
BWI5:00 pmBaltimore/Washington
2h 10m
MDW6:10 pmChicago Midway
Mar 3
MDW6:10 pmChicago Midway
1h 50m
BWI9:00 pmBaltimore/Washington
Southwest
Feb 22
DCA6:05 amWashington, D.C. Reagan-National
2h 10m
MDW7:15 amChicago Midway
Feb 24
MDW6:25 amChicago Midway
1h 50m
DCA9:15 amWashington, D.C. Reagan-National

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 $53. 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 $184.

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 $229. 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, Tuesday 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 $329.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $209 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $318. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Washington, D.C. when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $211 when searching 15 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Washington, D.C. for as low as $81 on momondo.

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

There are 1 cabin classes 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.

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

As of January 2025, prices for Washington, D.C. to Chicago Midway Airport flights are approximately 58% cheaper when compared to flights at the same time last year.

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

$34

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 $34. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $57.
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.

  • 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 $58Free CancellationRating
6.0
3,443 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.1
4,662 reviews
Search Southwest flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,521 reviews
Search Delta flights
United AirlinesPriceFrom $192Free CancellationRating
7.4
8,984 reviews
Search United Airlines 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 42 flights on this route every week with an average price of $312. Southwest is rated 8.1/10 by our users.


Traveling to a place near Chicago?

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


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