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Cheap flights from Washington, D.C. to Chicago Midway Airport from $53

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 1/30. 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 to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:00 am - 11:04 amBWI-MDW
5h 04m1 stop
12:15 pm - 3:07 pmMDW-BWI
1h 52mnonstop
$100Frontier
Find Deal
Wed, Nov 20 - Sat, Nov 23
4:33 pm - 5:37 pmBWI-MDW
2h 04mnonstop
11:33 am - 9:10 amMDW-BWI
20h 37m1 stop
$101Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
4:55 pm - 5:56 pmBWI-MDW
2h 01mnonstop
12:26 pm - 3:18 pmMDW-BWI
1h 52mnonstop
$103Frontier
Find Deal
Mon, Nov 11 - Thu, Nov 14
4:30 pm - 7:50 pmBWI-MDW
4h 20m1 stop
5:55 pm - 8:45 pmMDW-BWI
1h 50mnonstop
$179Southwest
Find Deal
Thu, Dec 5 - Sat, Dec 7
7:55 am - 9:00 amBWI-MDW
2h 05mnonstop
7:20 am - 10:10 amMDW-BWI
1h 50mnonstop
$195Southwest
Find Deal
Thu, Dec 5 - Thu, Dec 12
6:00 am - 8:50 amBWI-MDW
3h 50m1 stop
4:58 pm - 11:03 pmMDW-BWI
5h 05m1 stop
$196Delta
Find Deal
Wed, Dec 4 - Sat, Dec 7
6:00 am - 9:50 amBWI-MDW
4h 50m1 stop
12:44 pm - 6:42 pmMDW-BWI
4h 58m1 stop
$197Delta
Find Deal
Fri, Dec 6 - Thu, Dec 12
8:25 am - 9:40 amIAD-MDW
26h 15m3 stops
10:10 am - 11:20 amMDW-IAD
24h 10m3 stops
Sat, Nov 23 - Tue, Nov 26
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
12:05 pm - 10:24 pmMDW-IAD
9h 19m1 stop
$537Porter Airlines
Find Deal
Mon, Dec 2 - Fri, Dec 6
7:00 am - 12:00 pmIAD-MDW
6h 00m1 stop
12:05 pm - 10:24 pmMDW-IAD
9h 19m1 stop
$701Porter Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2
5:27 pm - 9:29 pmIAD-MDW
5h 02m1 stop
$53Frontier
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Thu, Jan 30
1:20 pm - 5:18 pmIAD-MDW
4h 58m1 stop
$54Frontier
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Thu, Dec 12
7:55 am - 9:00 amBWI-MDW
2h 05mnonstop
$69Southwest
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Wed, Dec 11
5:25 pm - 6:35 pmBWI-MDW
2h 10mnonstop
$70Southwest
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Tue, Jan 7
12:30 pm - 5:01 pmBWI-MDW
5h 31m1 stop
$98Delta
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Tue, Dec 10
6:00 am - 8:58 amIAD-MDW
3h 58m1 stop
$124Delta
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Tue, Dec 10
10:49 pm - 8:19 pmBWI-MDW
22h 30m2 stops
Thu, Nov 21
5:28 am - 7:58 pmBWI-MDW
15h 30m2 stops
Fri, Nov 15
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
$270Porter Airlines
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Mon, Dec 2
7:00 am - 4:40 pmIAD-MDW
10h 40m1 stop
$283Porter Airlines
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Sat, Dec 21
4:08 pm - 5:09 pmBWI-MDW
2h 01mnonstop
12:26 pm - 3:18 pmMDW-BWI
1h 52mnonstop
$199Frontier
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Thu, Nov 7 - Thu, Nov 14
5:04 pm - 11:56 pmBWI-MDW
7h 52m1 stop
12:26 pm - 3:18 pmMDW-BWI
1h 52mnonstop
$203Frontier
Find Deal
Sat, Nov 9 - Thu, Nov 14
3:42 pm - 4:43 pmBWI-MDW
2h 01mnonstop
1:13 pm - 4:05 pmMDW-BWI
1h 52mnonstop
$207Frontier
Find Deal
Sun, Nov 10 - Mon, Nov 11
5:35 pm - 6:40 pmBWI-MDW
2h 05mnonstop
5:30 pm - 8:20 pmMDW-BWI
1h 50mnonstop
$425Southwest
Find Deal
Sat, Nov 9 - Tue, Nov 12
3:55 pm - 6:55 pmBWI-MDW
4h 00m1 stop
5:55 pm - 8:45 pmMDW-BWI
1h 50mnonstop
$430Southwest
Find Deal
Sat, Nov 9 - Sat, Nov 16
6:05 am - 8:55 amIAD-MDW
3h 50m1 stop
6:00 am - 11:49 amMDW-IAD
4h 49m1 stop
$470Delta
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Sun, Nov 10 - Wed, Nov 20
6:05 am - 8:55 amIAD-MDW
3h 50m1 stop
5:42 pm - 11:22 pmMDW-IAD
4h 40m1 stop
$476Delta
Find Deal
Sat, Nov 9 - Wed, Nov 20
9:43 am - 7:42 amIAD-MDW
22h 59m2 stops
11:15 am - 11:20 amMDW-IAD
23h 05m3 stops
Thu, Nov 7 - Sun, Nov 10
5:25 am - 6:06 pmBWI-MDW
13h 41m2 stops
11:32 am - 11:34 amMDW-BWI
23h 02m3 stops
Sun, Nov 10 - Mon, Nov 11
6:06 pm - 6:29 pmIAD-MDW
25h 23m3 stops
9:35 am - 5:32 pmMDW-IAD
30h 57m3 stops
$1,648WestJet
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Wed, Nov 6 - Fri, Nov 8
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$63Frontier
Find Deal
Sat, Feb 15 - Wed, Feb 26
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
6:25 am - 9:17 amMDW-BWI
1h 52mnonstop
$67Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$68Frontier
Find Deal
Sat, Feb 15 - Sat, Feb 22
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$70Frontier
Find Deal
Sat, Feb 15 - Sat, Feb 22
4:18 pm - 5:22 pmBWI-MDW
2h 04mnonstop
6:25 am - 9:17 amMDW-BWI
1h 52mnonstop
$75Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
4:49 pm - 5:56 pmBWI-MDW
2h 07mnonstop
12:45 pm - 3:30 pmMDW-BWI
1h 45mnonstop
$77Frontier
Find Deal
Fri, Jan 31 - Mon, Feb 3
4:33 pm - 5:37 pmBWI-MDW
2h 04mnonstop
12:36 pm - 3:28 pmMDW-BWI
1h 52mnonstop
$78Frontier
Find Deal
Fri, Dec 13 - Mon, Dec 16
4:49 pm - 5:56 pmBWI-MDW
2h 07mnonstop
12:45 pm - 3:30 pmMDW-BWI
1h 45mnonstop
$80Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
7:55 am - 9:00 amBWI-MDW
2h 05mnonstop
7:20 am - 10:10 amMDW-BWI
1h 50mnonstop
$154Southwest
Find Deal
Wed, Dec 4 - Wed, Dec 11
12:50 pm - 2:00 pmBWI-MDW
2h 10mnonstop
10:30 am - 1:15 pmMDW-BWI
1h 45mnonstop
$158Southwest
Find Deal
Sat, Jan 11 - Mon, Jan 13

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
Nov 20
BWI7:00 amBaltimore/Washington
5h 04m
1 stop
MDW11:04 amChicago Midway
Nov 23
MDW12:15 pmChicago Midway
1h 52m
BWI3:07 pmBaltimore/Washington
Frontier
Dec 6
BWI4:33 pmBaltimore/Washington
2h 04m
MDW5:37 pmChicago Midway
Dec 9
MDW11:33 amChicago Midway
20h 37m
1 stop
BWI9:10 amBaltimore/Washington
Frontier
Nov 11
BWI4:55 pmBaltimore/Washington
2h 01m
MDW5:56 pmChicago Midway
Nov 14
MDW12:26 pmChicago Midway
1h 52m
BWI3:18 pmBaltimore/Washington

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
Dec 4
BWI6:00 amBaltimore/Washington
3h 50m
1 stop
MDW8:50 amChicago Midway
Dec 7
MDW4:58 pmChicago Midway
5h 05m
1 stop
BWI11:03 pmBaltimore/Washington
Delta
Dec 6
BWI6:00 amBaltimore/Washington
4h 50m
1 stop
MDW9:50 amChicago Midway
Dec 12
MDW12:44 pmChicago Midway
4h 58m
1 stop
BWI6:42 pmBaltimore/Washington
Delta
Dec 4
BWI6:00 amBaltimore/Washington
3h 50m
1 stop
MDW8:50 amChicago Midway
Dec 12
MDW5:50 pmChicago Midway
4h 52m
1 stop
BWI11:42 pmBaltimore/Washington

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 from Washington, D.C. to Chicago Midway Airport?

April. The cheapest time of year to fly to Chicago Midway Airport from Washington, D.C. is April. Most expensive is March

What is the cheapest day to depart Washington, D.C. for Chicago Midway Airport?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Sunday

When is the cheapest time to fly from Washington, D.C. to Chicago Midway Airport?

In the evening. Washington, D.C. to Chicago Midway Airport flights are approximately 41% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago Midway Airport from Washington, D.C.?

Frontier. Frontier, Southwest, and United Airlines are the most popular carriers operating from Washington, D.C. to Chicago Midway Airport

How far in advance should you book Washington, D.C. to Chicago Midway Airport flights?

57 days before. The cheapest time to buy a flight from Washington, D.C. to Chicago Midway Airport is approximately 57 days to departure

How many flights depart from Washington, D.C. to Chicago Midway Airport on average per day?

3 flights are operational weekly from Washington, D.C. to Chicago Midway Airport as of November 2024. The most popular departure time for this route is 6:00PM, with 36% of flights per day taking off in the evening.

How many flights depart from Washington, D.C. to Chicago Midway Airport on average per week?

As of November 2024, there are 21 flights per week flying from Washington, D.C. to Chicago Midway Airport. The most common day of the week flights depart is Monday, with 29% of flights taking off on this day.

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.

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

$53

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 $53. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $100.
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
6.1
3,572 reviews
Search Frontier flights
SouthwestPriceFrom $150Free CancellationRating
8.1
5,082 reviews
Search Southwest flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,830 reviews
Search Delta flights
United AirlinesPriceFrom $192Free CancellationRating
7.4
9,215 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 $150. Generally, Southwest has 21 flights on this route every week with an average price of $270. Southwest is rated 8.1/10 by our users.


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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