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Cheap flights from District of Columbia to Chicago from $74

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from District of Columbia to Chicago departing on 3/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
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
5:33 pm - 10:19 pm
IAD
-
MDW
5h 46m
1 stop
Frontier Logo
6:20 am - 4:28 pm
MDW
-
IAD
9h 08m
1 stop
$150Frontier
Mon, Jan 26 - Thu, Jan 29
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
$151Frontier
Thu, Feb 19 - Mon, Feb 23
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
$156Frontier
Thu, Feb 5 - Mon, Feb 9
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
$157Frontier
Thu, Jan 29 - Mon, Feb 2
Frontier Logo
5:33 pm - 10:19 pm
IAD
-
MDW
5h 46m
1 stop
Frontier Logo
6:20 am - 4:28 pm
MDW
-
IAD
9h 08m
1 stop
$160Frontier
Mon, Feb 2 - Thu, Feb 5
Frontier Logo
5:37 pm - 10:37 pm
IAD
-
MDW
6h 00m
1 stop
Frontier Logo
9:04 pm - 10:40 am
MDW
-
IAD
12h 36m
1 stop
$166Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
8:15 am - 2:26 pm
IAD
-
MDW
7h 11m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$170Frontier
Fri, Feb 20 - Mon, Feb 23
Southwest Logo
6:55 pm - 8:05 pm
DCA
-
MDW
2h 10mnonstop
Southwest Logo
1:55 pm - 4:40 pm
MDW
-
DCA
1h 45mnonstop
$211Southwest
Wed, Feb 11 - Sat, Feb 14
Southwest Logo
2:45 pm - 8:40 pm
DCA
-
MDW
6h 55m
1 stop
Southwest Logo
5:55 pm - 8:45 pm
MDW
-
DCA
1h 50mnonstop
$221Southwest
Wed, Feb 11 - Sat, Feb 14

Frontier flights from District of Columbia to Chicago Midway Airport

Our best Frontier deals on District of Columbia to Chicago Midway Airport flight tickets
Frontier
Feb 21
IAD10:29 amWashington, D.C. Dulles Intl
12h 04m
1 stop
MDW9:33 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
9h 08m
1 stop
IAD4:08 pmWashington, D.C. Dulles Intl
$143
Frontier
Jan 26
IAD5:33 pmWashington, D.C. Dulles Intl
5h 46m
1 stop
MDW10:19 pmChicago Midway
Jan 29
MDW6:20 amChicago Midway
9h 08m
1 stop
IAD4:28 pmWashington, D.C. Dulles Intl
$150
Frontier
Feb 19
IAD5:37 pmWashington, D.C. Dulles Intl
6h 00m
1 stop
MDW10:37 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
9h 08m
1 stop
IAD4:08 pmWashington, D.C. Dulles Intl
$151

Delta flights from District of Columbia to Chicago Midway Airport

Our best Delta deals on District of Columbia to Chicago Midway Airport flight tickets
Delta
Feb 7
DCA9:54 amWashington, D.C. Reagan-National
3h 52m
1 stop
MDW12:46 pmChicago Midway
Feb 14
MDW11:06 amChicago Midway
4h 54m
1 stop
DCA5:00 pmWashington, D.C. Reagan-National
$271
Delta
Feb 14
DCA8:59 amWashington, D.C. Reagan-National
7h 22m
1 stop
MDW3:21 pmChicago Midway
Feb 16
MDW6:20 pmChicago Midway
3h 37m
1 stop
DCA10:57 pmWashington, D.C. Reagan-National
$290
Delta
Feb 3
DCA9:54 amWashington, D.C. Reagan-National
3h 52m
1 stop
MDW12:46 pmChicago Midway
Feb 5
MDW6:35 pmChicago Midway
3h 22m
1 stop
DCA10:57 pmWashington, D.C. Reagan-National
$300

momondo Fare Finder

 
Customize your flight search to find flights from District of Columbia 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 14, 2026.
Use the filters below to find and compare flights from District of Columbia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:19 pm

1 stop5h 46m

Chicago Midway

Thu 1/29

6:20 am-4:28 pm

1 stop9h 08m

$150

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

$151

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

$156

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/29

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Mon 2/2

6:20 am-4:28 pm

1 stop9h 08m

$157

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 2/2

5:33 pm-10:19 pm

1 stop5h 46m

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

$160

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

Sun 2/22

9:04 pm-10:40 am

1 stop12h 36m

$166

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 2/20

8:15 am-2:26 pm

1 stop7h 11m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$170

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 2/11

6:55 pm-8:05 pm

Nonstop2h 10m

Chicago Midway

Sat 2/14

1:55 pm-4:40 pm

Nonstop1h 45m

$211

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 2/11

2:45 pm-8:40 pm

1 stop6h 55m

Chicago Midway

Sat 2/14

5:55 pm-8:45 pm

Nonstop1h 50m

$221

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 District of Columbia 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 District of Columbia, with most prices found around $187. If you are unable to visit Chicago Midway Airport during the month of February, then departing from District of Columbia 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 District of Columbia. 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 District of Columbia 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 District of Columbia 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 District of Columbia to Chicago Midway flight route?

Fly from Baltimore/Washington to Chicago Midway for the best District of Columbia - Chicago Midway flight prices

What cabin class options are available on District of Columbia to Chicago Midway flights?

There is only 1 cabin class available to choose from on District of Columbia 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 District of Columbia to Chicago Midway Airport flights?

You could potentially save up to 10% on your flight if you consider stops on a District of Columbia to Chicago Midway Airport flight.

Cheap District of Columbia to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from District of Columbia to Chicago Midway Airport

Best Price Found

$164

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from District of Columbia in the past 72 hours is $164. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $309.
The fastest flight from District of Columbia to Chicago Midway Airport takes 1h 55m
Direct flights go from District of Columbia to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from District of Columbia to Chicago Midway Airport?

    Prices for flights from District of Columbia to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from District of Columbia to Chicago Midway Airport?

  • How old do you have to be to fly from District of Columbia to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from District of Columbia to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from District of Columbia to Chicago Midway Airport?

Best airlines flying from District of Columbia to Chicago Midway Airport

Compare and see reviews for airlines that fly from District of Columbia 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
4,258 reviews
Search Southwest flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,042 reviews
Search Delta flights

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 District of Columbia to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from District of Columbia to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from District of Columbia to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for District of Columbia to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from District of Columbia to Chicago?

Once you have performed a search for District of Columbia to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from District of Columbia to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from District of Columbia are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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