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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 1/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:35 am - 5:38 pmIAD-MDW
13h 03m1 stop
Frontier Logo
6:12 am - 6:16 pmMDW-IAD
11h 04m1 stop
$146Frontier
Find Deal
Thu, Dec 18 - Thu, Jan 1
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$155Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
5:42 pm - 10:19 pmIAD-MDW
5h 37m1 stop
Frontier Logo
9:13 am - 4:55 pmMDW-IAD
6h 42m1 stop
$156Frontier
Find Deal
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$158Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$159Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$160Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
5:45 am - 1:59 pmIAD-MDW
9h 14m1 stop
Frontier Logo
6:15 am - 5:25 pmMDW-IAD
10h 10m1 stop
$162Frontier
Find Deal
Sat, Dec 6 - Mon, Dec 8
Frontier Logo
5:37 pm - 10:12 pmIAD-MDW
5h 35m1 stop
Frontier Logo
6:12 am - 6:16 pmMDW-IAD
11h 04m1 stop
$163Frontier
Find Deal
Tue, Dec 30 - Fri, Jan 2
Frontier Logo
6:05 am - 1:21 pmIAD-MDW
8h 16m1 stop
Frontier Logo
6:12 am - 6:16 pmMDW-IAD
11h 04m1 stop
$164Frontier
Find Deal
Wed, Dec 31 - Thu, Jan 1
Frontier Logo
5:42 pm - 10:17 pmIAD-MDW
5h 35m1 stop
Frontier Logo
8:19 pm - 11:43 amMDW-IAD
14h 24m2 stops
$171Frontier
Find Deal
Wed, Jan 7 - Thu, Jan 15

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
Dec 18
IAD5:35 amWashington, D.C. Dulles Intl
13h 03m
1 stop
MDW5:38 pmChicago Midway
Jan 1
MDW6:12 amChicago Midway
11h 04m
1 stop
IAD6:16 pmWashington, D.C. Dulles Intl
$146
Find similar
Frontier
Jan 8
IAD6:00 amWashington, D.C. Dulles Intl
6h 31m
1 stop
MDW11:31 amChicago Midway
Jan 12
MDW6:10 amChicago Midway
8h 17m
1 stop
IAD3:27 pmWashington, D.C. Dulles Intl
$154
Find similar
Frontier
Jan 8
IAD6:00 amWashington, D.C. Dulles Intl
6h 31m
1 stop
MDW11:31 amChicago Midway
Jan 12
MDW6:10 amChicago Midway
8h 17m
1 stop
IAD3:27 pmWashington, D.C. Dulles Intl
$155
Find similar

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
Dec 6
DCA6:05 amWashington, D.C. Reagan-National
2h 05m
MDW7:10 amChicago Midway
Dec 6
MDW12:50 pmChicago Midway
1h 50m
DCA3:40 pmWashington, D.C. Reagan-National
$231
Find similar
Southwest
Dec 24
DCA6:55 pmWashington, D.C. Reagan-National
2h 05m
MDW8:00 pmChicago Midway
Dec 31
MDW8:10 pmChicago Midway
1h 45m
DCA10:55 pmWashington, D.C. Reagan-National
$237
Find similar
Southwest
Feb 21
DCA6:15 amWashington, D.C. Reagan-National
2h 10m
MDW7:25 amChicago Midway
Feb 23
MDW3:10 pmChicago Midway
1h 45m
DCA5:55 pmWashington, D.C. Reagan-National
$238
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 November 23, 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

Thu 12/18

5:35 am-5:38 pm

1 stop13h 03m

Chicago Midway

Thu 1/1

6:12 am-6:16 pm

1 stop11h 04m

$146

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$155

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/15

5:42 pm-10:19 pm

1 stop5h 37m

Chicago Midway

Sun 1/18

9:13 am-4:55 pm

1 stop6h 42m

$156

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$159

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 12/6

5:45 am-1:59 pm

1 stop9h 14m

Chicago Midway

Mon 12/8

6:15 am-5:25 pm

1 stop10h 10m

$162

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 12/30

5:37 pm-10:12 pm

1 stop5h 35m

Chicago Midway

Fri 1/2

6:12 am-6:16 pm

1 stop11h 04m

$163

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 12/31

6:05 am-1:21 pm

1 stop8h 16m

Chicago Midway

Thu 1/1

6:12 am-6:16 pm

1 stop11h 04m

$164

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 1/7

5:42 pm-10:17 pm

1 stop5h 35m

Chicago Midway

Thu 1/15

8:19 pm-11:43 am

2 stops14h 24m

$171

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 $184. 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 $202.

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 $311. 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 $380.

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 $312 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $354. 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?

You could potentially save up to 11% on your flight if you consider stops on a District of Columbia to Chicago Midway Airport flight.

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

$156

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 $156. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $302.
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 $69Free CancellationRating
5.8
3,100 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
7,999 reviews
Search Delta flights
SouthwestPriceFrom $160Free CancellationRating
8.0
4,252 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
Benton Harbor
Saint Joseph
Portage
Lansing
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.

An easier way to manage your Chicago Midway Airport trip

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