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Cheap flights from Washington, D.C. to Chicago from $67

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 2/26. 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
5:30 am - 9:22 pmBWI-MDW
16h 52m1 stop
Frontier Logo
2:49 pm - 12:24 amMDW-BWI
8h 35m1 stop
$122Frontier
Find Deal
Sat, Dec 13 - Wed, Dec 17
Frontier Logo
8:37 am - 9:58 pmBWI-MDW
14h 21m1 stop
Frontier Logo
2:49 pm - 12:24 amMDW-BWI
8h 35m1 stop
$129Frontier
Find Deal
Mon, Dec 15 - Wed, Dec 17
Frontier Logo
5:30 am - 5:38 pmBWI-MDW
13h 08m1 stop
Frontier Logo
6:52 am - 12:29 amMDW-BWI
16h 37m1 stop
$130Frontier
Find Deal
Thu, Jan 1 - Tue, Jan 6
Frontier Logo
11:24 am - 10:19 pmBWI-MDW
11h 55m1 stop
Frontier Logo
5:01 pm - 12:36 amMDW-BWI
6h 35m1 stop
$133Frontier
Find Deal
Fri, Jan 30 - Sun, Feb 1
Frontier Logo
9:11 pm - 8:46 amBWI-MDW
36h 35m2 stops
Frontier Logo
2:49 pm - 12:24 amMDW-BWI
8h 35m1 stop
$135Frontier
Find Deal
Mon, Dec 15 - Wed, Dec 17
Southwest Logo
1:45 pm - 2:55 pmBWI-MDW
2h 10mnonstop
Southwest Logo
5:15 pm - 8:10 pmMDW-BWI
1h 55mnonstop
$139Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
10:40 am - 9:58 pmBWI-MDW
12h 18m1 stop
Multiple Airlines Logo
3:10 pm - 12:23 amMDW-BWI
8h 13m1 stop
$143Multiple Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Southwest Logo
1:45 pm - 2:55 pmBWI-MDW
2h 10mnonstop
Southwest Logo
7:05 am - 10:00 amMDW-BWI
1h 55mnonstop
$148Southwest
Find Deal
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
8:25 am - 9:35 amDCA-MDW
2h 10mnonstop
Southwest Logo
5:30 pm - 8:20 pmMDW-DCA
1h 50mnonstop
$231Southwest
Find Deal
Sat, Dec 13 - Sat, Dec 13
Southwest Logo
6:05 am - 7:20 amDCA-MDW
2h 15mnonstop
Southwest Logo
12:10 pm - 2:55 pmMDW-DCA
1h 45mnonstop
$234Southwest
Find Deal
Sat, Jan 17 - Sun, Jan 18

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
Dec 13
BWI5:30 amBaltimore/Washington
16h 52m
1 stop
MDW9:22 pmChicago Midway
Dec 17
MDW2:49 pmChicago Midway
8h 35m
1 stop
BWI12:24 amBaltimore/Washington
$122
Find similar
Frontier
Dec 7
BWI9:43 pmBaltimore/Washington
25h 15m
1 stop
MDW9:58 pmChicago Midway
Dec 9
MDW2:49 pmChicago Midway
8h 35m
1 stop
BWI12:24 amBaltimore/Washington
$128
Find similar
Frontier
Dec 15
BWI8:37 amBaltimore/Washington
14h 21m
1 stop
MDW9:58 pmChicago Midway
Dec 17
MDW2:49 pmChicago Midway
8h 35m
1 stop
BWI12:24 amBaltimore/Washington
$129
Find similar

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
Jan 8
BWI1:45 pmBaltimore/Washington
2h 10m
MDW2:55 pmChicago Midway
Jan 12
MDW5:15 pmChicago Midway
1h 55m
BWI8:10 pmBaltimore/Washington
$139
Find similar
Southwest
Jan 8
BWI1:45 pmBaltimore/Washington
2h 10m
MDW2:55 pmChicago Midway
Jan 11
MDW7:05 amChicago Midway
1h 55m
BWI10:00 amBaltimore/Washington
$148
Find similar
Southwest
Jan 9
BWI1:45 pmBaltimore/Washington
2h 10m
MDW2:55 pmChicago Midway
Jan 9
MDW5:15 pmChicago Midway
1h 55m
BWI8:10 pmBaltimore/Washington
$157
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 November 29, 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

Sat 12/13

5:30 am-9:22 pm

1 stop16h 52m

Chicago Midway

Wed 12/17

2:49 pm-12:24 am

1 stop8h 35m

$122

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 12/15

8:37 am-9:58 pm

1 stop14h 21m

Chicago Midway

Wed 12/17

2:49 pm-12:24 am

1 stop8h 35m

$129

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/1

5:30 am-5:38 pm

1 stop13h 08m

Chicago Midway

Tue 1/6

6:52 am-12:29 am

1 stop16h 37m

$130

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/30

11:24 am-10:19 pm

1 stop11h 55m

Chicago Midway

Sun 2/1

5:01 pm-12:36 am

1 stop6h 35m

$133

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 12/15

9:11 pm-8:46 am

2 stops36h 35m

Chicago Midway

Wed 12/17

2:49 pm-12:24 am

1 stop8h 35m

$135

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/8

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Mon 1/12

5:15 pm-8:10 pm

Nonstop1h 55m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 12/11

10:40 am-9:58 pm

1 stop12h 18m

Chicago Midway

Mon 12/15

3:10 pm-12:23 am

1 stop8h 13m

$143

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 1/8

1:45 pm-2:55 pm

Nonstop2h 10m

Chicago Midway

Sun 1/11

7:05 am-10:00 am

Nonstop1h 55m

$148

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 12/13

8:25 am-9:35 am

Nonstop2h 10m

Chicago Midway

Sat 12/13

5:30 pm-8:20 pm

Nonstop1h 50m

$231

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 1/17

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Sun 1/18

12:10 pm-2:55 pm

Nonstop1h 45m

$234

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 $184. 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 $308. 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 $378.

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 $298 when looking at flights departing in the evening. Try not to purchase tickets in the morning 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

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?

As of November 2025, prices for Washington, D.C. to Chicago Midway Airport flights are approximately 3% 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

$108

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 $108. The best round-trip flight deal from Washington, D.C. to Chicago Midway Airport found on momondo in the last 72 hours is $186.
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 2h 05m.

  • 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 $64Free CancellationRating
5.8
3,100 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,011 reviews
Search Delta flights
SouthwestPriceFrom $160Free CancellationRating
8.0
4,253 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 $160. Generally, Southwest has 12 flights on this route every week with an average price of $304. 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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