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Cheap flights from Chicago Midway Airport to District of Columbia from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to District of Columbia departing on 7/28. 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 Chicago Midway Airport to District of Columbia

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
Frontier Logo
6:49 am - 11:07 am
IAD
-
MDW
5h 18m
1 stop
$235Frontier
Wed, Jul 22 - Sat, Jul 25
Southwest Logo
6:35 am - 11:35 am
MDW
-
DCA
4h 00m
1 stop
Southwest Logo
6:00 am - 1:20 pm
DCA
-
MDW
8h 20m
2 stops
$236Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
8:55 pm - 11:50 pm
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:10 am - 7:10 am
DCA
-
MDW
2h 00mnonstop
$237Southwest
Wed, Jul 29 - Sat, Aug 1
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
$238Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 11:26 pm
MDW
-
IAD
3h 44m
1 stop
Delta Logo
6:00 am - 10:10 am
IAD
-
MDW
5h 10m
1 stop
$238Delta
Sat, Aug 8 - Sat, Aug 15
Frontier Logo
7:25 am - 5:36 pm
MDW
-
IAD
9h 11m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$240Frontier
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
7:50 am - 3:55 pm
MDW
-
DCA
7h 05m
2 stops
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$241Southwest
Sat, Aug 29 - Mon, Aug 31
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$241Frontier
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$242Frontier
Thu, Aug 20 - Mon, Aug 24
Delta Logo
6:45 pm - 11:09 pm
MDW
-
DCA
3h 24m
1 stop
Delta Logo
6:25 pm - 10:10 pm
DCA
-
MDW
4h 45m
1 stop
$248Delta
Wed, Oct 21 - Mon, Nov 9

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Delta flights from Chicago Midway Airport to District of Columbia

Our best Delta deals on Chicago Midway Airport to District of Columbia flight tickets
Delta
Aug 8
MDW6:42 pmChicago Midway
3h 44m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
Aug 15
IAD6:00 amWashington, D.C. Dulles Intl
5h 10m
1 stop
MDW10:10 amChicago Midway
$238
Delta
Sep 24
MDW10:48 amChicago Midway
6h 33m
1 stop
IAD6:21 pmWashington, D.C. Dulles Intl
Sep 26
IAD6:09 pmWashington, D.C. Dulles Intl
5h 36m
1 stop
MDW10:45 pmChicago Midway
$248
Delta
Sep 3
MDW5:10 pmChicago Midway
6h 24m
1 stop
IAD12:34 amWashington, D.C. Dulles Intl
Sep 5
IAD5:47 pmWashington, D.C. Dulles Intl
5h 49m
1 stop
MDW10:36 pmChicago Midway
$257

Frontier flights from Chicago Midway Airport to District of Columbia

Our best Frontier deals on Chicago Midway Airport to District of Columbia flight tickets
Frontier
Jul 22
MDW6:05 amChicago Midway
10h 09m
1 stop
IAD5:14 pmWashington, D.C. Dulles Intl
Jul 25
IAD6:49 amWashington, D.C. Dulles Intl
5h 18m
1 stop
MDW11:07 amChicago Midway
$235
Frontier
Sep 17
MDW7:25 amChicago Midway
9h 11m
1 stop
IAD5:36 pmWashington, D.C. Dulles Intl
Sep 21
IAD7:00 amWashington, D.C. Dulles Intl
4h 58m
1 stop
MDW10:58 amChicago Midway
$240
Frontier
Aug 20
MDW11:50 amChicago Midway
10h 02m
1 stop
IAD10:52 pmWashington, D.C. Dulles Intl
Aug 24
IAD6:20 amWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:55 amChicago Midway
$241

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to District of Columbia 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 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to District of Columbia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 7/22

6:05 am-5:14 pm

1 stop10h 09m

Washington, D.C. Dulles Intl

Sat 7/25

6:49 am-11:07 am

1 stop5h 18m

$235

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 8/15

6:35 am-11:35 am

1 stop4h 00m

Washington, D.C. Reagan-National

Sat 8/22

6:00 am-1:20 pm

2 stops8h 20m

$236
Quickest round-trip

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 7/29

8:55 pm-11:50 pm

Nonstop1h 55m

Washington, D.C. Reagan-National

Sat 8/1

6:10 am-7:10 am

Nonstop2h 00m

$237

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 8/8

6:42 pm-10:59 pm

1 stop3h 17m

Washington, D.C. Reagan-National

Sat 8/15

6:30 pm-10:36 pm

1 stop5h 06m

$238

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 8/8

6:42 pm-11:26 pm

1 stop3h 44m

Washington, D.C. Dulles Intl

Sat 8/15

6:00 am-10:10 am

1 stop5h 10m

$238

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 9/17

7:25 am-5:36 pm

1 stop9h 11m

Washington, D.C. Dulles Intl

Mon 9/21

7:00 am-10:58 am

1 stop4h 58m

$240

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 8/29

7:50 am-3:55 pm

2 stops7h 05m

Washington, D.C. Reagan-National

Mon 8/31

1:00 pm-5:50 pm

2 stops5h 50m

$241

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 8/20

11:50 am-10:52 pm

1 stop10h 02m

Washington, D.C. Dulles Intl

Mon 8/24

6:20 am-10:55 am

1 stop5h 35m

$241

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 8/20

11:50 am-10:52 pm

1 stop10h 02m

Washington, D.C. Dulles Intl

Mon 8/24

6:20 am-10:55 am

1 stop5h 35m

$242

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 10/21

6:45 pm-11:09 pm

1 stop3h 24m

Washington, D.C. Reagan-National

Mon 11/9

6:25 pm-10:10 pm

1 stop4h 45m

$248

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 District of Columbia from

How to get the cheapest flight ticket from Chicago Midway Airport to District of Columbia

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 District of Columbia?

In general, November is the cheapest month to fly from Chicago Midway Airport to District of Columbia. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $61. If you don’t want to visit District of Columbia in November, then you should wait until September to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $76.

What is the cheapest day to depart on your flight to District of Columbia?

The cheapest day to depart on your flight to District of Columbia is on a Wednesday when prices can be found for as low as $278. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $460.

What is the cheapest time of day to depart on your flight to District of Columbia?

Flying to District of Columbia from Chicago Midway Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $306 when looking at flights departing at noon. Flights to District of Columbia are more costly in the evening, with an average ticket price of $335. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to District of Columbia flight route?

Fly from Chicago Midway to Washington, D.C. Reagan-National for the best Chicago Midway - District of Columbia flight prices

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

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

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

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

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

Best Price Found

$168

Fastest flight time

1h 45m

Direct flights

Every day

Airports in District of Columbia

2 airports
The best one-way flight to District of Columbia from Chicago Midway Airport in the past 72 hours is $168. The best round-trip flight deal from Chicago Midway Airport to District of Columbia found on momondo in the last 72 hours is $278.
The fastest flight from Chicago Midway Airport to District of Columbia takes 1h 45m
Direct flights go from Chicago Midway Airport to District of Columbia every day.
There are 2 airports in District of Columbia. From Chicago Midway Airport there are direct flights to Washington, D.C. Reagan-National (DCA).
Search flight deals

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

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

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

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

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

    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 Chicago Midway Airport to District of Columbia.

  • What documentation or ID do you need to fly to District of Columbia?

    The required travel and health documents for your District of Columbia 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 District of Columbia. 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 Chicago Midway Airport to District of Columbia?

Best airlines flying from Chicago Midway Airport to District of Columbia

Compare and see reviews for airlines that fly from Chicago Midway Airport to District of Columbia with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $90Free CancellationRating
5.6
2,847 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
7.9
4,252 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to District of Columbia?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to District of Columbia from Chicago.

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

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

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

Once all potential Chicago to District of Columbia flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to District of Columbia flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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