Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $78

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. Reagan-National Airport to Chicago departing on 12/4. 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 Washington, D.C. Reagan-National Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:00 am - 11:08 amDCA-MDW
28h 08m1 stop
Frontier Logo
12:18 pm - 9:59 pmMDW-DCA
8h 41m1 stop
$200Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
2:00 pm - 11:08 amDCA-MDW
22h 08m1 stop
Frontier Logo
12:18 pm - 1:06 pmMDW-DCA
23h 48m1 stop
$201Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
6:00 pm - 11:08 amDCA-MDW
18h 08m1 stop
Frontier Logo
12:18 pm - 1:06 pmMDW-DCA
23h 48m1 stop
$202Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15
Southwest Logo
8:45 pm - 9:55 pmDCA-MDW
2h 10mnonstop
Southwest Logo
12:15 pm - 3:00 pmMDW-DCA
1h 45mnonstop
$223Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
6:05 am - 9:40 amDCA-MDW
4h 35m1 stop
Southwest Logo
6:00 am - 8:45 amMDW-DCA
1h 45mnonstop
$233Southwest
Find Deal
Wed, Dec 3 - Sun, Dec 7
Southwest Logo
6:40 pm - 7:50 pmDCA-MDW
2h 10mnonstop
Southwest Logo
9:10 am - 12:00 pmMDW-DCA
1h 50mnonstop
$237Southwest
Find Deal
Sat, Feb 14 - Sun, Feb 15
Southwest Logo
6:30 am - 3:20 pmDCA-MDW
9h 50m2 stops
Southwest Logo
9:15 am - 12:00 pmMDW-DCA
1h 45mnonstop
$238Southwest
Find Deal
Sat, Dec 6 - Sun, Dec 7
Delta Logo
9:36 am - 12:34 pmDCA-MDW
3h 58m1 stop
Delta Logo
6:40 pm - 11:08 pmMDW-DCA
3h 28m1 stop
$243Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
6:00 am - 11:06 amDCA-MDW
6h 06m1 stop
Delta Logo
6:00 am - 12:57 pmMDW-DCA
5h 57m1 stop
$257Delta
Find Deal
Wed, Dec 31 - Thu, Jan 1
Delta Logo
2:00 pm - 6:18 pmDCA-MDW
5h 18m1 stop
Delta Logo
6:40 pm - 11:08 pmMDW-DCA
3h 28m1 stop
$265Delta
Find Deal
Tue, Dec 9 - Thu, Dec 11

Frontier flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

Our best Frontier deals on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight tickets
Frontier
Nov 13
DCA2:00 pmWashington, D.C. Reagan-National
22h 30m
1 stop
MDW11:30 amChicago Midway
Nov 17
MDW12:30 pmChicago Midway
27h 29m
1 stop
DCA4:59 pmWashington, D.C. Reagan-National
$190
Find similar
Frontier
Dec 4
DCA8:00 amWashington, D.C. Reagan-National
28h 08m
1 stop
MDW11:08 amChicago Midway
Dec 8
MDW12:18 pmChicago Midway
8h 41m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National
$200
Find similar
Frontier
Dec 4
DCA2:00 pmWashington, D.C. Reagan-National
22h 08m
1 stop
MDW11:08 amChicago Midway
Dec 8
MDW12:18 pmChicago Midway
23h 48m
1 stop
DCA1:06 pmWashington, D.C. Reagan-National
$201
Find similar

Southwest flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

Our best Southwest deals on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight tickets
Southwest
Dec 3
DCA8:45 pmWashington, D.C. Reagan-National
2h 10m
MDW9:55 pmChicago Midway
Dec 10
MDW12:15 pmChicago Midway
1h 45m
DCA3:00 pmWashington, D.C. Reagan-National
$223
Find similar
Southwest
Dec 3
DCA6:05 amWashington, D.C. Reagan-National
4h 35m
1 stop
MDW9:40 amChicago Midway
Dec 7
MDW6:00 amChicago Midway
1h 45m
DCA8:45 amWashington, D.C. Reagan-National
$233
Find similar
Southwest
Feb 14
DCA6:40 pmWashington, D.C. Reagan-National
2h 10m
MDW7:50 pmChicago Midway
Feb 15
MDW9:10 amChicago Midway
1h 50m
DCA12:00 pmWashington, D.C. Reagan-National
$237
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Reagan-National Airport 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 6, 2025.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/4

8:00 am-11:08 am

1 stop28h 08m

Chicago Midway

Mon 12/8

12:18 pm-9:59 pm

1 stop8h 41m

$200

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/4

2:00 pm-11:08 am

1 stop22h 08m

Chicago Midway

Mon 12/8

12:18 pm-1:06 pm

1 stop23h 48m

$201

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/11

6:00 pm-11:08 am

1 stop18h 08m

Chicago Midway

Mon 12/15

12:18 pm-1:06 pm

1 stop23h 48m

$202

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/3

8:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Wed 12/10

12:15 pm-3:00 pm

Nonstop1h 45m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/3

6:05 am-9:40 am

1 stop4h 35m

Chicago Midway

Sun 12/7

6:00 am-8:45 am

Nonstop1h 45m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/14

6:40 pm-7:50 pm

Nonstop2h 10m

Chicago Midway

Sun 2/15

9:10 am-12:00 pm

Nonstop1h 50m

$237

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 12/6

6:30 am-3:20 pm

2 stops9h 50m

Chicago Midway

Sun 12/7

9:15 am-12:00 pm

Nonstop1h 45m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 12/5

9:36 am-12:34 pm

1 stop3h 58m

Chicago Midway

Sun 12/7

6:40 pm-11:08 pm

1 stop3h 28m

$243

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/31

6:00 am-11:06 am

1 stop6h 06m

Chicago Midway

Thu 1/1

6:00 am-12:57 pm

1 stop5h 57m

$257

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 12/9

2:00 pm-6:18 pm

1 stop5h 18m

Chicago Midway

Thu 12/11

6:40 pm-11:08 pm

1 stop3h 28m

$265

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 Washington, D.C. Reagan-National Airport 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Reagan-National Airport, with most prices found around $247. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Washington, D.C. Reagan-National Airport during the month July is also very affordable. Most momondo users find prices during this month for around $263.

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 Washington, D.C. Reagan-National Airport. 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 Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National to Chicago Midway flight route?

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. Reagan-National - 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 Washington, D.C. Reagan-National Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $315 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 Washington, D.C. Reagan-National Airport for as low as $215 on momondo.

What cabin class options are available on Washington, D.C. Reagan-National to Chicago Midway flights?

There is only 1 cabin class available to choose from on Washington, D.C. Reagan-National 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 Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. Reagan-National Airport to Chicago Midway Airport.

How have Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight prices changed over time?

When to book flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Washington, D.C. Reagan-National Airport to Chicago Midway Airport (DCA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

Best Price Found

$156

Fastest flight time

2h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Washington, D.C. Reagan-National Airport in the past 72 hours is $156. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago Midway Airport found on momondo in the last 72 hours is $302.
The fastest flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport takes 2h 00m
Direct flights go from Washington, D.C. Reagan-National Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Washington, D.C. Reagan-National to Chicago Midway by plane?

    Washington, D.C. Reagan-National and Chicago Midway are 598.5 mi apart from one another. By plane, this route typically takes 2h 05m.

  • When did momondo last update prices for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    Prices for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

  • What is the most popular airline from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

Best airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $99Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
SouthwestPriceFrom $179Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

  • Southwest Flights From Washington, D.C. Reagan-National Airport to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, operating 36 flights/week on average for this route. A good Southwest flight deal for Washington, D.C. Reagan-National Airport to Chicago Midway Airport starts from $179 round-trip, up to an average price of $309. Our users have rated Southwest at 8.0/10.

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 Washington, D.C. to Chicago?

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 Chicago from Washington, D.C..

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Washington, D.C. with this policy.

How can momondo help me find flights from Washington, D.C. to Chicago?

momondo helps you find the best flight between Washington, D.C. and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Washington, D.C. to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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
Sat 12/6
Sat 12/13
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago