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Cheap flights from District of Columbia to Chicago from $108

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 4/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from District of Columbia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:26 pm - 10:02 pm
IAD
-
MDW
5h 36m
1 stop
Multiple Airlines Logo
9:14 am - 5:28 pm
MDW
-
IAD
7h 14m
1 stop
$219Multiple Airlines
sam., mai 9 - jeu., mai 21
Southwest Logo
2:45 pm - 5:50 pm
DCA
-
MDW
4h 05m
1 stop
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
$219Southwest
lun., mai 4 - mar., mai 5
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$220Frontier
jeu., mai 28 - mar., juin 2
Frontier Logo
1:26 pm - 8:04 am
IAD
-
MDW
19h 38m
1 stop
Frontier Logo
6:00 am - 12:14 pm
MDW
-
IAD
5h 14m
1 stop
$221Frontier
dim., avr. 19 - ven., mai 1
Frontier Logo
8:20 am - 7:31 pm
IAD
-
MDW
12h 11m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$222Frontier
mar., avr. 21 - jeu., avr. 23
Southwest Logo
3:40 pm - 4:50 pm
DCA
-
MDW
2h 10mnonstop
Southwest Logo
9:15 am - 8:55 pm
MDW
-
DCA
10h 40m
2 stops
$223Southwest
mer., mai 6 - sam., mai 9
Frontier Logo
9:21 am - 7:31 pm
IAD
-
MDW
11h 10m
1 stop
Frontier Logo
6:00 am - 5:34 pm
MDW
-
IAD
10h 34m
1 stop
$223Frontier
ven., avr. 24 - lun., avr. 27
Frontier Logo
5:26 pm - 10:02 pm
IAD
-
MDW
5h 36m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$224Frontier
jeu., mai 14 - dim., mai 17
Delta Logo
6:00 pm - 10:28 pm
DCA
-
MDW
5h 28m
1 stop
Delta Logo
1:24 pm - 6:59 pm
MDW
-
DCA
4h 35m
1 stop
$226Delta
mer., avr. 29 - mer., mai 6
Delta Logo
5:33 pm - 9:09 pm
IAD
-
MDW
4h 36m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
lun., mai 11 - mar., mai 12

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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
Apr 29
DCA6:00 pmWashington, D.C. Reagan-National
5h 28m
1 stop
MDW10:28 pmChicago Midway
May 6
MDW1:24 pmChicago Midway
4h 35m
1 stop
DCA6:59 pmWashington, D.C. Reagan-National
$226
Delta
May 11
IAD5:33 pmWashington, D.C. Dulles Intl
4h 36m
1 stop
MDW9:09 pmChicago Midway
May 12
MDW6:36 pmChicago Midway
3h 20m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$228
Delta
Apr 27
DCA6:00 pmWashington, D.C. Reagan-National
5h 28m
1 stop
MDW10:28 pmChicago Midway
May 13
MDW5:10 pmChicago Midway
5h 34m
1 stop
DCA11:44 pmWashington, D.C. Reagan-National
$236

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
May 28
IAD11:07 amWashington, D.C. Dulles Intl
11h 55m
1 stop
MDW10:02 pmChicago Midway
Jun 2
MDW6:00 amChicago Midway
9h 21m
1 stop
IAD4:21 pmWashington, D.C. Dulles Intl
$220
Frontier
Apr 19
IAD1:26 pmWashington, D.C. Dulles Intl
19h 38m
1 stop
MDW8:04 amChicago Midway
May 1
MDW6:00 amChicago Midway
5h 14m
1 stop
IAD12:14 pmWashington, D.C. Dulles Intl
$221
Frontier
Apr 21
IAD8:20 amWashington, D.C. Dulles Intl
12h 11m
1 stop
MDW7:31 pmChicago Midway
Apr 23
MDW2:15 pmChicago Midway
9h 21m
1 stop
IAD12:36 amWashington, D.C. Dulles Intl
$222

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 avril 17, 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

Cheapest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

sam. 5/9

5:26 pm-10:02 pm

1 stop5h 36m

Chicago Midway

jeu. 5/21

9:14 am-5:28 pm

1 stop7h 14m

$219
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

lun. 5/4

2:45 pm-5:50 pm

1 stop4h 05m

Chicago Midway

mar. 5/5

1:55 pm-6:40 pm

1 stop3h 45m

$219

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

jeu. 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

mar. 6/2

6:00 am-4:21 pm

1 stop9h 21m

$220

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

dim. 4/19

1:26 pm-8:04 am

1 stop19h 38m

Chicago Midway

ven. 5/1

6:00 am-12:14 pm

1 stop5h 14m

$221

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mar. 4/21

8:20 am-7:31 pm

1 stop12h 11m

Chicago Midway

jeu. 4/23

2:15 pm-12:36 am

1 stop9h 21m

$222

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mer. 5/6

3:40 pm-4:50 pm

Nonstop2h 10m

Chicago Midway

sam. 5/9

9:15 am-8:55 pm

2 stops10h 40m

$223

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

ven. 4/24

9:21 am-7:31 pm

1 stop11h 10m

Chicago Midway

lun. 4/27

6:00 am-5:34 pm

1 stop10h 34m

$223

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

jeu. 5/14

5:26 pm-10:02 pm

1 stop5h 36m

Chicago Midway

dim. 5/17

6:00 am-4:21 pm

1 stop9h 21m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mer. 4/29

6:00 pm-10:28 pm

1 stop5h 28m

Chicago Midway

mer. 5/6

1:24 pm-6:59 pm

1 stop4h 35m

$226

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

lun. 5/11

5:33 pm-9:09 pm

1 stop4h 36m

Chicago Midway

mar. 5/12

6:36 pm-10:56 pm

1 stop3h 20m

$228

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 August is, on average, the cheapest month to fly to Chicago Midway Airport from District of Columbia, with most prices found around $207. If you are unable to visit Chicago Midway Airport during the month of August, then departing from District of Columbia during the month September is also very affordable. Most momondo users find prices during this month for around $228.

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 District of Columbia. The lowest ticket price found for a Saturday departure recently was $328. 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 $384.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $364. 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 Washington, D.C. Reagan-National 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 6% 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

$189

Fastest flight time

1h 55m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from District of Columbia in the past 72 hours is $189. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $301.
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 on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
Search flight deals

Frequently asked questions about flying from District of Columbia to Chicago Midway Airport

  • 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 $95Free CancellationRating
5.7
2,987 reviews
Search Frontier flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,328 reviews
Search Southwest flights
DeltaPriceFrom $194Free CancellationRating
7.9
8,406 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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.

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