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Cheap flights from Washington, D.C. to Chicago from $56

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 9/19. 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

Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$80Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$89Frontier
Find Deal
Sun, Sep 21 - Thu, Sep 25
Frontier Logo
2:29 pm - 3:33 pmBWI-MDW
2h 04mnonstop
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
$102Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$107Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
5:55 pm - 6:59 pmBWI-MDW
2h 04mnonstop
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
$108Frontier
Find Deal
Sat, Oct 18 - Thu, Oct 23
Southwest Logo
7:55 pm - 8:55 pmBWI-MDW
2h 00mnonstop
Southwest Logo
12:30 pm - 3:20 pmMDW-BWI
1h 50mnonstop
$161Southwest
Find Deal
Sat, Oct 11 - Wed, Oct 15
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
Allegiant Air Logo
9:32 am - 3:23 pmMDW-IAD
4h 51m1 stop
$174Allegiant Air
Find Deal
Mon, Aug 18 - Fri, Aug 22
Southwest Logo
8:25 am - 9:25 amDCA-MDW
2h 00mnonstop
Southwest Logo
12:45 pm - 3:40 pmMDW-DCA
1h 55mnonstop
$217Southwest
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
5:25 pm - 9:12 pmIAD-MDW
4h 47m1 stop
Delta Logo
9:30 am - 11:26 pmMDW-IAD
12h 56m1 stop
$227Delta
Find Deal
Sat, Aug 30 - Tue, Sep 2
Delta Logo
6:00 am - 9:40 amIAD-MDW
4h 40m1 stop
Delta Logo
6:23 pm - 11:01 pmMDW-IAD
3h 38m1 stop
$237Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25

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
Oct 3
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
Oct 6
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
$80
Find similar
Frontier
Sep 21
BWI5:40 pmBaltimore/Washington
2h 03m
MDW6:43 pmChicago Midway
Sep 25
MDW1:49 pmChicago Midway
2h 01m
BWI4:50 pmBaltimore/Washington
$89
Find similar
Frontier
Oct 17
BWI2:29 pmBaltimore/Washington
2h 04m
MDW3:33 pmChicago Midway
Oct 20
MDW1:59 pmChicago Midway
1h 56m
BWI4:55 pmBaltimore/Washington
$102
Find similar

Allegiant Air flights from Washington, D.C. to Chicago Midway Airport

Our best Allegiant Air deals on Washington, D.C. to Chicago Midway Airport flight tickets
Allegiant Air
Aug 18
IAD1:22 pmWashington, D.C. Dulles Intl
5h 55m
1 stop
MDW6:17 pmChicago Midway
Aug 22
MDW9:32 amChicago Midway
4h 51m
1 stop
IAD3:23 pmWashington, D.C. Dulles Intl
$174
Find similar
Allegiant Air
Aug 14
IAD9:12 pmWashington, D.C. Dulles Intl
17h 52m
2 stops
MDW2:04 pmChicago Midway
Aug 17
MDW11:03 amChicago Midway
24h 29m
2 stops
IAD12:32 pmWashington, D.C. Dulles Intl
$369
Find similar
Allegiant Air
Aug 14
IAD9:12 pmWashington, D.C. Dulles Intl
17h 52m
2 stops
MDW2:04 pmChicago Midway
Aug 17
MDW11:03 amChicago Midway
24h 29m
2 stops
IAD12:32 pmWashington, D.C. Dulles Intl
$373
Find similar

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 July 31, 2025.
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

Fri 10/3

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Mon 10/6

1:49 pm-4:50 pm

Nonstop2h 01m

$80

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 9/21

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Thu 9/25

1:49 pm-4:50 pm

Nonstop2h 01m

$89

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 10/17

2:29 pm-3:33 pm

Nonstop2h 04m

Chicago Midway

Mon 10/20

1:59 pm-4:55 pm

Nonstop1h 56m

$102

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 9/11

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Sun 9/14

1:49 pm-4:50 pm

Nonstop2h 01m

$107

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/18

5:55 pm-6:59 pm

Nonstop2h 04m

Chicago Midway

Thu 10/23

1:59 pm-4:55 pm

Nonstop1h 56m

$108

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 10/11

7:55 pm-8:55 pm

Nonstop2h 00m

Chicago Midway

Wed 10/15

12:30 pm-3:20 pm

Nonstop1h 50m

$161

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

12:45 pm-3:40 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/30

5:25 pm-9:12 pm

1 stop4h 47m

Chicago Midway

Tue 9/2

9:30 am-11:26 pm

1 stop12h 56m

$227

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/22

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sat 10/25

6:23 pm-11:01 pm

1 stop3h 38m

$237

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 $181. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Washington, D.C. during the month September is also very affordable. Most momondo users find prices during this month for around $200.

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 $325. 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, Monday 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 $393.

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 $316 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $352. 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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $236 when searching 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 $151 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.

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?

As of July 2025, prices for Washington, D.C. to Chicago Midway Airport flights are approximately 27% 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

$56

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 $56. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $80.
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 $61Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $161Free CancellationRating
8.0
4,246 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 $161. Generally, Southwest has 20 flights on this route every week with an average price of $297. 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
Crown Point
Munster
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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