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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 8/23. 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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Find the cheapest flights from District of Columbia to Chicago

Cheap round-trip flights

Frontier Logo
9:30 am - 2:01 pmIAD-MDW
5h 31m1 stop
Frontier Logo
3:03 pm - 9:39 pmMDW-IAD
5h 36m1 stop
$178Frontier
Find Deal
mié., ago. 27 - mié., sep. 3
Frontier Logo
9:15 am - 3:58 pmIAD-MDW
7h 43m1 stop
Frontier Logo
9:00 am - 7:55 pmMDW-IAD
9h 55m1 stop
$179Frontier
Find Deal
mié., sep. 24 - mié., oct. 1
Frontier Logo
9:15 am - 3:58 pmIAD-MDW
7h 43m1 stop
Frontier Logo
9:00 am - 7:55 pmMDW-IAD
9h 55m1 stop
$181Frontier
Find Deal
mié., sep. 10 - mié., sep. 17
Frontier Logo
4:22 pm - 11:25 pmIAD-MDW
8h 03m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$183Frontier
Find Deal
sáb., oct. 11 - mar., oct. 14
Southwest Logo
3:15 pm - 4:25 pmDCA-MDW
2h 10mnonstop
Southwest Logo
3:25 pm - 6:15 pmMDW-DCA
1h 50mnonstop
$189Southwest
Find Deal
mar., sep. 9 - mar., sep. 16
Southwest Logo
9:00 am - 10:00 amDCA-MDW
2h 00mnonstop
Southwest Logo
10:20 am - 6:55 pmMDW-DCA
7h 35m1 stop
$199Southwest
Find Deal
mié., oct. 1 - mar., oct. 7
Southwest Logo
6:35 pm - 7:30 pmDCA-MDW
1h 55mnonstop
Southwest Logo
8:00 am - 10:50 amMDW-DCA
1h 50mnonstop
$203Southwest
Find Deal
mié., sep. 3 - sáb., sep. 6
Delta Logo
6:00 am - 8:35 amDCA-MDW
3h 35m1 stop
Delta Logo
6:17 pm - 10:59 pmMDW-DCA
3h 42m1 stop
$209Delta
Find Deal
mié., sep. 3 - mar., sep. 9
Delta Logo
5:52 pm - 10:14 pmIAD-MDW
5h 22m1 stop
Delta Logo
3:00 pm - 11:40 pmMDW-IAD
7h 40m1 stop
$223Delta
Find Deal
mié., oct. 22 - sáb., oct. 25
Delta Logo
6:00 am - 8:35 amDCA-MDW
3h 35m1 stop
Delta Logo
1:08 pm - 5:25 pmMDW-DCA
3h 17m1 stop
$223Delta
Find Deal
mié., sep. 3 - sáb., sep. 6

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 9
DCA3:15 pmWashington, D.C. Reagan-National
2h 10m
MDW4:25 pmChicago Midway
Sep 16
MDW3:25 pmChicago Midway
1h 50m
DCA6:15 pmWashington, D.C. Reagan-National
$189
Find similar
Southwest
Oct 1
DCA9:00 amWashington, D.C. Reagan-National
2h 00m
MDW10:00 amChicago Midway
Oct 7
MDW10:20 amChicago Midway
7h 35m
1 stop
DCA6:55 pmWashington, D.C. Reagan-National
$199
Find similar
Southwest
Sep 3
DCA6:35 pmWashington, D.C. Reagan-National
1h 55m
MDW7:30 pmChicago Midway
Sep 6
MDW8:00 amChicago Midway
1h 50m
DCA10:50 amWashington, D.C. Reagan-National
$203
Find similar

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
Aug 27
IAD9:30 amWashington, D.C. Dulles Intl
5h 31m
1 stop
MDW2:01 pmChicago Midway
Sep 3
MDW3:03 pmChicago Midway
5h 36m
1 stop
IAD9:39 pmWashington, D.C. Dulles Intl
$178
Find similar
Frontier
Sep 24
IAD9:15 amWashington, D.C. Dulles Intl
7h 43m
1 stop
MDW3:58 pmChicago Midway
Oct 1
MDW9:00 amChicago Midway
9h 55m
1 stop
IAD7:55 pmWashington, D.C. Dulles Intl
$179
Find similar
Frontier
Sep 10
IAD9:15 amWashington, D.C. Dulles Intl
7h 43m
1 stop
MDW3:58 pmChicago Midway
Sep 17
MDW9:00 amChicago Midway
9h 55m
1 stop
IAD7:55 pmWashington, D.C. Dulles Intl
$181
Find similar

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 agosto 11, 2025.
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

mié. 8/27

9:30 am-2:01 pm

1 stop5h 31m

Chicago Midway

mié. 9/3

3:03 pm-9:39 pm

1 stop5h 36m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 9/24

9:15 am-3:58 pm

1 stop7h 43m

Chicago Midway

mié. 10/1

9:00 am-7:55 pm

1 stop9h 55m

$179

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 9/10

9:15 am-3:58 pm

1 stop7h 43m

Chicago Midway

mié. 9/17

9:00 am-7:55 pm

1 stop9h 55m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

sáb. 10/11

4:22 pm-11:25 pm

1 stop8h 03m

Chicago Midway

mar. 10/14

8:05 am-7:46 pm

1 stop10h 41m

$183

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mar. 9/9

3:15 pm-4:25 pm

Nonstop2h 10m

Chicago Midway

mar. 9/16

3:25 pm-6:15 pm

Nonstop1h 50m

$189

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 10/1

9:00 am-10:00 am

Nonstop2h 00m

Chicago Midway

mar. 10/7

10:20 am-6:55 pm

1 stop7h 35m

$199

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 9/3

6:35 pm-7:30 pm

Nonstop1h 55m

Chicago Midway

sáb. 9/6

8:00 am-10:50 am

Nonstop1h 50m

$203

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

mar. 9/9

6:17 pm-10:59 pm

1 stop3h 42m

$209

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 10/22

5:52 pm-10:14 pm

1 stop5h 22m

Chicago Midway

sáb. 10/25

3:00 pm-11:40 pm

1 stop7h 40m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 9/3

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

sáb. 9/6

1:08 pm-5:25 pm

1 stop3h 17m

$223

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from District of Columbia, with most prices found around $181. If you are unable to visit Chicago Midway Airport during the month of February, then departing from District of Columbia during the month August is also very affordable. Most momondo users find prices during this month for around $199.

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 $322. 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, Monday 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 $392.

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 $317 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $351. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from District of Columbia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $238 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from District of Columbia for as low as $151 on momondo.

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

There are 1 cabin classes 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

$89

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 $89. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $178.
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 $62Free CancellationRating
5.8
3,221 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
8.0
7,979 reviews
Search Delta flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
SouthwestPriceFrom $161Free CancellationRating
8.0
4,248 reviews
Search Southwest 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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Saint Joseph
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Portage
Schererville
Valparaiso
Crown Point
Munster
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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