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Cheap flights from Chicago Midway Airport to District of Columbia 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 Chicago Midway Airport to District of Columbia departing on 6/12. 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 Chicago Midway Airport to District of Columbia

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:23 pm - 8:04 pm
MDW
-
IAD
21h 41m
1 stop
Multiple Airlines Logo
8:57 pm - 11:04 am
IAD
-
MDW
15h 07m
1 stop
$227Multiple Airlines
Fri, Jun 12 - Fri, Jun 19
Southwest Logo
7:25 pm - 10:15 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
11:45 am - 5:55 pm
DCA
-
MDW
7h 10m
1 stop
$228Southwest
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
6:00 am - 4:52 pm
MDW
-
IAD
9h 52m
1 stop
Frontier Logo
11:17 am - 10:08 pm
IAD
-
MDW
11h 51m
1 stop
$228Frontier
Thu, Jul 2 - Fri, Jul 10
Frontier Logo
12:04 pm - 11:22 pm
MDW
-
IAD
10h 18m
1 stop
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
$229Frontier
Fri, Jun 19 - Mon, Jun 22
Southwest Logo
5:40 am - 8:25 am
MDW
-
DCA
1h 45mnonstop
Southwest Logo
7:25 am - 12:15 pm
DCA
-
MDW
5h 50m
1 stop
$230Southwest
Wed, Jun 10 - Wed, Jun 17
Frontier Logo
12:04 pm - 11:22 pm
MDW
-
IAD
10h 18m
1 stop
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
$230Frontier
Fri, Jun 19 - Mon, Jun 22
Southwest Logo
1:40 pm - 4:30 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
6:05 am - 1:10 pm
DCA
-
MDW
8h 05m
2 stops
$233Southwest
Tue, Oct 20 - Sat, Oct 24
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
Frontier Logo
8:47 pm - 11:09 am
IAD
-
MDW
15h 22m
1 stop
$234Frontier
Thu, May 28 - Thu, May 28
Delta Logo
1:22 pm - 6:59 pm
MDW
-
DCA
4h 37m
1 stop
Delta Logo
6:25 pm - 10:17 pm
DCA
-
MDW
4h 52m
1 stop
$237Delta
Sat, Jun 6 - Tue, Jun 23
Delta Logo
1:00 pm - 6:59 pm
MDW
-
DCA
4h 59m
1 stop
Delta Logo
7:00 am - 11:56 am
DCA
-
MDW
5h 56m
1 stop
$238Delta
Wed, Oct 21 - Sat, Oct 24

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 2
MDW6:00 amChicago Midway
9h 52m
1 stop
IAD4:52 pmWashington, D.C. Dulles Intl
Jul 10
IAD11:17 amWashington, D.C. Dulles Intl
11h 51m
1 stop
MDW10:08 pmChicago Midway
$228
Frontier
Jun 19
MDW12:04 pmChicago Midway
10h 18m
1 stop
IAD11:22 pmWashington, D.C. Dulles Intl
Jun 22
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
$229
Frontier
Jun 1
MDW6:00 amChicago Midway
10h 27m
1 stop
IAD5:27 pmWashington, D.C. Dulles Intl
Jun 10
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
$230

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
Jun 6
MDW1:22 pmChicago Midway
4h 37m
1 stop
DCA6:59 pmWashington, D.C. Reagan-National
Jun 23
DCA6:25 pmWashington, D.C. Reagan-National
4h 52m
1 stop
MDW10:17 pmChicago Midway
$237
Delta
Oct 21
MDW1:00 pmChicago Midway
4h 59m
1 stop
DCA6:59 pmWashington, D.C. Reagan-National
Oct 24
DCA7:00 amWashington, D.C. Reagan-National
5h 56m
1 stop
MDW11:56 amChicago Midway
$238
Delta
Jul 1
MDW6:00 amChicago Midway
7h 02m
1 stop
IAD2:02 pmWashington, D.C. Dulles Intl
Jul 7
IAD6:00 amWashington, D.C. Dulles Intl
4h 08m
1 stop
MDW9:08 amChicago Midway
$258

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 May 18, 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

Fri 6/12

9:23 pm-8:04 pm

1 stop21h 41m

Washington, D.C. Dulles Intl

Fri 6/19

8:57 pm-11:04 am

1 stop15h 07m

$227

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 6/3

7:25 pm-10:15 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 6/10

11:45 am-5:55 pm

1 stop7h 10m

$228

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 7/2

6:00 am-4:52 pm

1 stop9h 52m

Washington, D.C. Dulles Intl

Fri 7/10

11:17 am-10:08 pm

1 stop11h 51m

$228

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 6/19

12:04 pm-11:22 pm

1 stop10h 18m

Washington, D.C. Dulles Intl

Mon 6/22

11:17 am-10:11 pm

1 stop11h 54m

$229
Quickest round-trip

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 6/10

5:40 am-8:25 am

Nonstop1h 45m

Washington, D.C. Reagan-National

Wed 6/17

7:25 am-12:15 pm

1 stop5h 50m

$230

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 6/19

12:04 pm-11:22 pm

1 stop10h 18m

Washington, D.C. Dulles Intl

Mon 6/22

11:17 am-10:11 pm

1 stop11h 54m

$230

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Tue 10/20

1:40 pm-4:30 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Sat 10/24

6:05 am-1:10 pm

2 stops8h 05m

$233

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 5/28

6:00 am-4:21 pm

1 stop9h 21m

Washington, D.C. Dulles Intl

Thu 5/28

8:47 pm-11:09 am

1 stop15h 22m

$234

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 6/6

1:22 pm-6:59 pm

1 stop4h 37m

Washington, D.C. Reagan-National

Tue 6/23

6:25 pm-10:17 pm

1 stop4h 52m

$237

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 10/21

1:00 pm-6:59 pm

1 stop4h 59m

Washington, D.C. Reagan-National

Sat 10/24

7:00 am-11:56 am

1 stop5h 56m

$238

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 $271. 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 $419.

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 $308 when looking at flights departing at noon. Flights to District of Columbia are more costly in the evening, with an average ticket price of $322. 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

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

$154

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 $154. The best round-trip flight deal from Chicago Midway Airport to District of Columbia found on momondo in the last 72 hours is $287.
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 $95Free CancellationRating
5.6
2,946 reviews
Search Frontier flights
SouthwestPriceFrom $159Free CancellationRating
7.9
4,286 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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