Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from District of Columbia to Chicago 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 District of Columbia to Chicago departing on 7/21. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from District of Columbia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:45 am - 5:05 pm
DCA
-
MDW
6h 20m
2 stops
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$236Southwest
Tue, Jul 28 - Mon, Aug 10
Delta Logo
6:10 am - 9:17 am
IAD
-
MDW
4h 07m
1 stop
Delta Logo
6:42 pm - 11:26 pm
MDW
-
IAD
3h 44m
1 stop
$238Delta
Mon, Aug 10 - Thu, Aug 13
Southwest Logo
3:35 pm - 4:40 pm
DCA
-
MDW
2h 05mnonstop
Southwest Logo
5:45 am - 8:30 am
MDW
-
DCA
1h 45mnonstop
$238Southwest
Mon, Aug 10 - Thu, Aug 13
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Frontier Logo
12:11 pm - 10:55 pm
MDW
-
IAD
9h 44m
1 stop
$240Frontier
Fri, Jul 3 - Tue, Jul 7
Delta Logo
6:10 am - 8:45 am
IAD
-
MDW
3h 35m
1 stop
Delta Logo
5:25 pm - 12:20 am
MDW
-
IAD
5h 55m
1 stop
$241Delta
Thu, Oct 8 - Wed, Oct 14
Delta Logo
6:59 am - 11:55 am
DCA
-
MDW
5h 56m
1 stop
Delta Logo
5:10 pm - 11:43 pm
MDW
-
DCA
5h 33m
1 stop
$241Delta
Wed, Sep 16 - Mon, Sep 21
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Frontier Logo
6:00 am - 4:00 pm
MDW
-
IAD
9h 00m
1 stop
$244Frontier
Wed, Jun 24 - Sat, Jun 27
Southwest Logo
6:05 am - 7:00 am
DCA
-
MDW
1h 55mnonstop
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$244Southwest
Tue, Sep 8 - Thu, Sep 10
Frontier Logo
11:11 am - 10:11 pm
IAD
-
MDW
12h 00m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$245Frontier
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
9:15 pm - 10:10 pm
DCA
-
MDW
1h 55mnonstop
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$245Southwest
Thu, Aug 6 - Mon, Aug 10

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
Jul 3
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
Jul 7
MDW12:11 pmChicago Midway
9h 44m
1 stop
IAD10:55 pmWashington, D.C. Dulles Intl
$240
Frontier
Jun 24
IAD11:17 amWashington, D.C. Dulles Intl
11h 54m
1 stop
MDW10:11 pmChicago Midway
Jun 27
MDW6:00 amChicago Midway
9h 00m
1 stop
IAD4:00 pmWashington, D.C. Dulles Intl
$244
Frontier
Aug 20
IAD11:11 amWashington, D.C. Dulles Intl
12h 00m
1 stop
MDW10:11 pmChicago Midway
Aug 22
MDW6:00 amChicago Midway
9h 20m
1 stop
IAD4:20 pmWashington, D.C. Dulles Intl
$245

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
Aug 10
IAD6:10 amWashington, D.C. Dulles Intl
4h 07m
1 stop
MDW9:17 amChicago Midway
Aug 13
MDW6:42 pmChicago Midway
3h 44m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
$238
Delta
Aug 5
IAD6:10 amWashington, D.C. Dulles Intl
4h 07m
1 stop
MDW9:17 amChicago Midway
Aug 6
MDW6:42 pmChicago Midway
3h 44m
1 stop
IAD11:26 pmWashington, D.C. Dulles Intl
$241
Delta
Sep 17
DCA6:00 amWashington, D.C. Reagan-National
4h 53m
1 stop
MDW9:53 amChicago Midway
Sep 21
MDW5:10 pmChicago Midway
5h 33m
1 stop
DCA11:43 pmWashington, D.C. Reagan-National
$259

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 June 3, 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

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 7/28

11:45 am-5:05 pm

2 stops6h 20m

Chicago Midway

Mon 8/10

9:00 pm-11:55 pm

Nonstop1h 55m

$236

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/10

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Thu 8/13

6:42 pm-11:26 pm

1 stop3h 44m

$238
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 8/10

3:35 pm-4:40 pm

Nonstop2h 05m

Chicago Midway

Thu 8/13

5:45 am-8:30 am

Nonstop1h 45m

$238

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 7/3

11:17 am-10:11 pm

1 stop11h 54m

Chicago Midway

Tue 7/7

12:11 pm-10:55 pm

1 stop9h 44m

$240

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/8

6:10 am-8:45 am

1 stop3h 35m

Chicago Midway

Wed 10/14

5:25 pm-12:20 am

1 stop5h 55m

$241

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/16

6:59 am-11:55 am

1 stop5h 56m

Chicago Midway

Mon 9/21

5:10 pm-11:43 pm

1 stop5h 33m

$241

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 6/24

11:17 am-10:11 pm

1 stop11h 54m

Chicago Midway

Sat 6/27

6:00 am-4:00 pm

1 stop9h 00m

$244

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 9/8

6:05 am-7:00 am

Nonstop1h 55m

Chicago Midway

Thu 9/10

9:00 pm-11:55 pm

Nonstop1h 55m

$244

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/20

11:11 am-10:11 pm

1 stop12h 00m

Chicago Midway

Sat 8/22

6:00 am-4:20 pm

1 stop9h 20m

$245

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/6

9:15 pm-10:10 pm

Nonstop1h 55m

Chicago Midway

Mon 8/10

9:00 pm-11:55 pm

Nonstop1h 55m

$245

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 April is, on average, the cheapest month to fly to Chicago Midway Airport from District of Columbia, with most prices found around $70. If you are unable to visit Chicago Midway Airport during the month of April, then departing from District of Columbia during the month September is also very affordable. Most momondo users find prices during this month for around $77.

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 $336. 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 $411.

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 $333 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $374. 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 is only 1 cabin class 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

$185

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 $185. The best round-trip flight deal from District of Columbia to Chicago Midway Airport found on momondo in the last 72 hours is $311.
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
2,920 reviews
Search Frontier flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,398 reviews
Search Delta flights
SouthwestPriceFrom $158Free CancellationRating
8.0
4,255 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
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 7/3
Fri 7/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago