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Cheap flights from District of Columbia to Chicago from $79

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 4/8. 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 District of Columbia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
1:31 pm - 4:00 pm
IAD
-
MDW
27h 29m
1 stop
Frontier Logo
9:04 am - 7:27 am
MDW
-
IAD
21h 23m
1 stop
$181Frontier
Fri, Apr 17 - Sun, Apr 19
Frontier Logo
5:34 pm - 10:21 pm
IAD
-
MDW
5h 47m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$182Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
5:34 pm - 10:21 pm
IAD
-
MDW
5h 47m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$183Frontier
Thu, Apr 9 - Thu, Apr 16
Delta Logo
6:00 am - 8:47 am
IAD
-
MDW
3h 47m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
IAD
3h 25m
1 stop
$188Delta
Mon, Apr 13 - Fri, Apr 17
Delta Logo
12:29 pm - 5:54 pm
DCA
-
MDW
6h 25m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$188Delta
Wed, Apr 8 - Fri, Apr 10
Frontier Logo
7:00 am - 8:54 pm
IAD
-
MDW
14h 54m
1 stop
Frontier Logo
6:00 am - 11:56 pm
MDW
-
IAD
16h 56m
1 stop
$190Frontier
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
7:55 am - 9:00 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
8:05 pm - 10:55 pm
MDW
-
DCA
1h 50mnonstop
$191Southwest
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
12:55 pm - 9:58 pm
IAD
-
MDW
10h 03m
1 stop
Frontier Logo
9:14 am - 7:27 am
MDW
-
IAD
21h 13m
1 stop
$192Frontier
Fri, Apr 10 - Fri, Apr 17
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
4:20 pm - 7:10 pm
MDW
-
DCA
1h 50mnonstop
$194Southwest
Sat, Apr 18 - Wed, Apr 22
Multiple Airlines Logo
10:25 pm - 1:00 pm
IAD
-
MDW
15h 35m
2 stops
Multiple Airlines Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$197Multiple Airlines
Mon, Apr 13 - Wed, Apr 15

Southwest flights from District of Columbia to Chicago Midway Airport

Our best Southwest deals on District of Columbia to Chicago Midway Airport flight tickets
Southwest
Apr 9
DCA7:55 amWashington, D.C. Reagan-National
2h 05m
MDW9:00 amChicago Midway
Apr 13
MDW8:05 pmChicago Midway
1h 50m
DCA10:55 pmWashington, D.C. Reagan-National
$191
Southwest
Apr 25
DCA6:40 amWashington, D.C. Reagan-National
2h 05m
MDW7:45 amChicago Midway
Apr 28
MDW7:25 pmChicago Midway
1h 50m
DCA10:15 pmWashington, D.C. Reagan-National
$194
Southwest
Apr 11
DCA6:40 amWashington, D.C. Reagan-National
2h 05m
MDW7:45 amChicago Midway
Apr 18
MDW6:35 pmChicago Midway
1h 55m
DCA9:30 pmWashington, D.C. Reagan-National
$197

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
Apr 17
IAD1:31 pmWashington, D.C. Dulles Intl
27h 29m
1 stop
MDW4:00 pmChicago Midway
Apr 19
MDW9:04 amChicago Midway
21h 23m
1 stop
IAD7:27 amWashington, D.C. Dulles Intl
$181
Frontier
Apr 9
IAD5:34 pmWashington, D.C. Dulles Intl
5h 47m
1 stop
MDW10:21 pmChicago Midway
Apr 16
MDW2:15 pmChicago Midway
9h 21m
1 stop
IAD12:36 amWashington, D.C. Dulles Intl
$182
Frontier
Apr 9
IAD5:34 pmWashington, D.C. Dulles Intl
5h 47m
1 stop
MDW10:21 pmChicago Midway
Apr 16
MDW2:15 pmChicago Midway
9h 21m
1 stop
IAD12:36 amWashington, D.C. Dulles Intl
$183

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 February 25, 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

Fri 4/17

1:31 pm-4:00 pm

1 stop27h 29m

Chicago Midway

Sun 4/19

9:04 am-7:27 am

1 stop21h 23m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/9

5:34 pm-10:21 pm

1 stop5h 47m

Chicago Midway

Thu 4/16

2:15 pm-12:36 am

1 stop9h 21m

$182

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/9

5:34 pm-10:21 pm

1 stop5h 47m

Chicago Midway

Thu 4/16

2:15 pm-12:36 am

1 stop9h 21m

$183

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Fri 4/17

6:38 pm-11:03 pm

1 stop3h 25m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/8

12:29 pm-5:54 pm

1 stop6h 25m

Chicago Midway

Fri 4/10

6:34 pm-10:51 pm

1 stop3h 17m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 3/17

7:00 am-8:54 pm

1 stop14h 54m

Chicago Midway

Tue 3/24

6:00 am-11:56 pm

1 stop16h 56m

$190

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 4/9

7:55 am-9:00 am

Nonstop2h 05m

Chicago Midway

Mon 4/13

8:05 pm-10:55 pm

Nonstop1h 50m

$191

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/10

12:55 pm-9:58 pm

1 stop10h 03m

Chicago Midway

Fri 4/17

9:14 am-7:27 am

1 stop21h 13m

$192

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 4/18

6:40 am-7:45 am

Nonstop2h 05m

Chicago Midway

Wed 4/22

4:20 pm-7:10 pm

Nonstop1h 50m

$194

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Wed 4/15

2:15 pm-12:36 am

1 stop9h 21m

$197

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from District of Columbia, with most prices found around $202. 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, 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 $318. 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 $378.

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 $309 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $356. 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?

No. A direct flight is the cheapest option for a flight between District of Columbia to Chicago Midway Airport.

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

$166

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 $166. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $303.
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 $70Free CancellationRating
5.7
3,040 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
DeltaPriceFrom $194Free CancellationRating
7.9
8,237 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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