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Cheap flights from District of Columbia to Chicago from $89

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 9/7. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
7:50 am - 5:51 pm
IAD
-
MDW
11h 01m
1 stop
Frontier Logo
6:25 am - 5:18 pm
MDW
-
IAD
9h 53m
1 stop
$200Frontier
Sat, Sep 12 - Fri, Sep 18
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$200Frontier
Fri, Aug 28 - Sat, Aug 29
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$200Frontier
Wed, Aug 26 - Wed, Sep 2
Delta Logo
11:10 am - 4:59 pm
IAD
-
MDW
6h 49m
1 stop
Delta Logo
5:37 pm - 11:14 pm
MDW
-
IAD
4h 37m
1 stop
$202Delta
Sun, Sep 6 - Tue, Sep 8
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
Delta Logo
6:05 am - 11:27 am
MDW
-
DCA
4h 22m
1 stop
$202Delta
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
3:15 pm - 6:55 pm
DCA
-
MDW
4h 40m
1 stop
Southwest Logo
8:15 am - 2:55 pm
MDW
-
DCA
5h 40m
1 stop
$202Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
Southwest Logo
8:50 am - 3:00 pm
MDW
-
DCA
5h 10m
1 stop
$202Southwest
Mon, Aug 24 - Wed, Aug 26
Delta Logo
6:00 am - 9:42 am
IAD
-
MDW
4h 42m
1 stop
Delta Logo
9:30 am - 4:26 pm
MDW
-
IAD
5h 56m
1 stop
$238Delta
Mon, Nov 23 - Tue, Dec 1
Multiple Airlines Logo
6:30 pm - 2:59 pm
IAD
-
MDW
21h 29m
2 stops
Multiple Airlines Logo
9:26 pm - 6:29 pm
MDW
-
IAD
20h 03m
1 stop
$363Multiple Airlines
Sun, Aug 16 - Sun, Aug 23
Multiple Airlines Logo
1:30 pm - 10:58 am
IAD
-
MDW
22h 28m
2 stops
Multiple Airlines Logo
11:38 am - 6:45 pm
MDW
-
IAD
6h 07m
1 stop
$454Multiple Airlines
Thu, Oct 8 - Sun, Oct 11

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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
Sep 16
DCA6:00 amWashington, D.C. Reagan-National
7h 05m
2 stops
MDW12:05 pmChicago Midway
Sep 22
MDW10:10 amChicago Midway
5h 00m
1 stop
DCA4:10 pmWashington, D.C. Reagan-National
$202
Southwest
Oct 6
DCA6:05 amWashington, D.C. Reagan-National
7h 00m
2 stops
MDW12:05 pmChicago Midway
Oct 7
MDW3:30 pmChicago Midway
7h 25m
2 stops
DCA11:55 pmWashington, D.C. Reagan-National
$203
Southwest
Sep 11
DCA8:15 amWashington, D.C. Reagan-National
5h 00m
1 stop
MDW12:15 pmChicago Midway
Sep 19
MDW10:05 amChicago Midway
9h 45m
2 stops
DCA8:50 pmWashington, D.C. Reagan-National
$207

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
Sep 6
IAD11:10 amWashington, D.C. Dulles Intl
6h 49m
1 stop
MDW4:59 pmChicago Midway
Sep 8
MDW5:37 pmChicago Midway
4h 37m
1 stop
IAD11:14 pmWashington, D.C. Dulles Intl
$202
Delta
Aug 24
DCA6:30 pmWashington, D.C. Reagan-National
5h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 31
MDW5:45 pmChicago Midway
4h 14m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$238
Delta
Aug 24
DCA6:30 pmWashington, D.C. Reagan-National
5h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 31
MDW5:45 pmChicago Midway
4h 14m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$243

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 July 30, 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

Sat 9/12

7:50 am-5:51 pm

1 stop11h 01m

Chicago Midway

Fri 9/18

6:25 am-5:18 pm

1 stop9h 53m

$200

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 8/28

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Sat 8/29

6:05 am-5:14 pm

1 stop10h 09m

$200

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 8/26

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Wed 9/2

6:05 am-5:14 pm

1 stop10h 09m

$200

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 9/6

11:10 am-4:59 pm

1 stop6h 49m

Chicago Midway

Tue 9/8

5:37 pm-11:14 pm

1 stop4h 37m

$202
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/5

6:30 pm-10:36 pm

1 stop5h 06m

Chicago Midway

Sun 9/6

6:05 am-11:27 am

1 stop4h 22m

$202

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 9/11

3:15 pm-6:55 pm

1 stop4h 40m

Chicago Midway

Mon 9/14

8:15 am-2:55 pm

1 stop5h 40m

$202

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 8/24

1:00 pm-5:50 pm

2 stops5h 50m

Chicago Midway

Wed 8/26

8:50 am-3:00 pm

1 stop5h 10m

$202

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 11/23

6:00 am-9:42 am

1 stop4h 42m

Chicago Midway

Tue 12/1

9:30 am-4:26 pm

1 stop5h 56m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 8/16

6:30 pm-2:59 pm

2 stops21h 29m

Chicago Midway

Sun 8/23

9:26 pm-6:29 pm

1 stop20h 03m

$363

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/8

1:30 pm-10:58 am

2 stops22h 28m

Chicago Midway

Sun 10/11

11:38 am-6:45 pm

1 stop6h 07m

$454

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from District of Columbia, with most prices found around $265. If you are unable to visit Chicago Midway Airport during the month of September, then departing from District of Columbia during the month January is also very affordable. Most momondo users find prices during this month for around $302.

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 $341. 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 $428.

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 $299 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $384. 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 Airport flights?

There are 2 cabin classes available to choose from on District of Columbia to Chicago Midway Airport 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

$183

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 $183. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $275.
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

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 $90Free CancellationRating
5.6
2,747 reviews
Search Frontier flights
DeltaPriceFrom $149Free CancellationRating
7.8
8,489 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,227 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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