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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $114

1 adult
1 adult, Economy, 0 bags

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.
Southwest Logo
6:10 am - 7:15 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
5:35 am - 8:25 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$228Southwest
Tue, Nov 17 - Tue, Nov 24
Southwest Logo
9:40 am - 10:50 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
9:00 pm - 11:45 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
$228Southwest
Tue, Jan 12 - Wed, Jan 13
Southwest Logo
8:55 pm - 10:10 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
12:05 pm - 2:55 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$230Southwest
Wed, Nov 18 - Thu, Nov 19
Southwest Logo
6:00 am - 7:05 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
7:25 am - 10:15 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$230Southwest
Sat, Dec 5 - Wed, Dec 9
Southwest Logo
1:00 pm - 2:15 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:50 am - 8:45 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 55mnonstop
$230Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
3:35 pm - 4:50 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
1:30 pm - 4:15 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
$233Southwest
Thu, Dec 3 - Thu, Dec 10
Southwest Logo
2:40 pm - 5:50 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 10m1 stop Lambert-St Louis
Southwest Logo
5:35 am - 8:25 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$233Southwest
Tue, Nov 17 - Tue, Nov 24
Southwest Logo
7:00 pm - 8:20 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
1:45 pm - 6:30 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
3h 45m1 stop Lambert-St Louis
$233Southwest
Tue, Jan 12 - Wed, Jan 13
Delta Logo
6:10 am - 9:32 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 22m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:27 pm - 11:44 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
10h 17m1 stop Minneapolis St Paul
$309Delta
Thu, Nov 5 - Sat, Nov 7
Delta Logo
6:26 pm - 10:33 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
5h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 pm - 11:44 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
10h 17m1 stop Minneapolis St Paul
$309Delta
Wed, Nov 4 - Sat, Nov 7

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

Our best Delta deals on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight tickets
Delta
Nov 4
DCA6:26 pmWashington, D.C. Reagan-National
5h 07m
1 stop
MDW10:33 pmChicago Midway
Nov 7
MDW12:27 pmChicago Midway
10h 17m
1 stop
DCA11:44 pmWashington, D.C. Reagan-National
$309
Delta
Dec 5
DCA9:45 amWashington, D.C. Reagan-National
4h 16m
1 stop
MDW1:01 pmChicago Midway
Dec 8
MDW1:02 pmChicago Midway
4h 23m
1 stop
DCA6:25 pmWashington, D.C. Reagan-National
$317
Delta
Nov 1
DCA9:40 amWashington, D.C. Reagan-National
4h 07m
1 stop
MDW12:47 pmChicago Midway
Nov 4
MDW11:39 amChicago Midway
4h 47m
1 stop
DCA5:26 pmWashington, D.C. Reagan-National
$425

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
Nov 17
DCA6:10 amWashington, D.C. Reagan-National
2h 05m
MDW7:15 amChicago Midway
Nov 24
MDW5:35 amChicago Midway
1h 50m
DCA8:25 amWashington, D.C. Reagan-National
$228
Southwest
Nov 18
DCA8:55 pmWashington, D.C. Reagan-National
2h 15m
MDW10:10 pmChicago Midway
Nov 19
MDW12:05 pmChicago Midway
1h 50m
DCA2:55 pmWashington, D.C. Reagan-National
$230
Southwest
Nov 17
DCA2:40 pmWashington, D.C. Reagan-National
4h 10m
1 stop
MDW5:50 pmChicago Midway
Nov 24
MDW5:35 amChicago Midway
1h 50m
DCA8:25 amWashington, D.C. Reagan-National
$233

momondo Fare Finder

 
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.

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Route

Depart

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Price

Cheapest round-trip
Quickest round-trip

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Tue 11/17

6:10 am-7:15 am

Nonstop2h 05m

Chicago Midway

Tue 11/24

5:35 am-8:25 am

Nonstop1h 50m

$228

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Tue 1/12

9:40 am-10:50 am

Nonstop2h 10m

Chicago Midway

Wed 1/13

9:00 pm-11:45 pm

Nonstop1h 45m

$228

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Wed 11/18

8:55 pm-10:10 pm

Nonstop2h 15m

Chicago Midway

Thu 11/19

12:05 pm-2:55 pm

Nonstop1h 50m

$230

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Sat 12/5

6:00 am-7:05 am

Nonstop2h 05m

Chicago Midway

Wed 12/9

7:25 am-10:15 am

Nonstop1h 50m

$230

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Wed 12/2

1:00 pm-2:15 pm

Nonstop2h 15m

Chicago Midway

Sat 12/5

5:50 am-8:45 am

Nonstop1h 55m

$230

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Thu 12/3

3:35 pm-4:50 pm

Nonstop2h 15m

Chicago Midway

Thu 12/10

1:30 pm-4:15 pm

Nonstop1h 45m

$233

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Tue 11/17

2:40 pm-5:50 pm

1 stop4h 10m

Chicago Midway

Tue 11/24

5:35 am-8:25 am

Nonstop1h 50m

$233

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Tue 1/12

7:00 pm-8:20 pm

Nonstop2h 20m

Chicago Midway

Wed 1/13

1:45 pm-6:30 pm

1 stop3h 45m

$233

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Thu 11/5

6:10 am-9:32 am

1 stop4h 22m

Chicago Midway

Sat 11/7

12:27 pm-11:44 pm

1 stop10h 17m

$309

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Wed 11/4

6:26 pm-10:33 pm

1 stop5h 07m

Chicago Midway

Sat 11/7

12:27 pm-11:44 pm

1 stop10h 17m

$309

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 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 typical price of a round-trip flight between Washington, D.C. Reagan-National Airport and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $308 to $505.
The lowest price recently found on this route was $228.

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Reagan-National Airport, with most prices found around $316. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Washington, D.C. Reagan-National Airport during the month February is also very affordable. Most momondo users find prices during this month for around $325.

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 Washington, D.C. Reagan-National Airport. The lowest ticket price found for a Saturday departure recently was $348. 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 $435.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $342 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $400. 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 from Washington, D.C. Reagan-National Airport 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 $383 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 $262 on momondo.

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

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

You could potentially save up to 25% on your flight if you consider stops on a Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight.

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

As of October 2026, prices for Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights are approximately 120% more expensive when compared to flights at the same time last year.

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

$114

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 $114. 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 $228.
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

Frequently asked questions about flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

  • 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 00m.

  • 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
SouthwestPriceFrom $236Free CancellationRating
7.9
4,209 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 31 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 $236 round-trip, up to an average price of $381. Our users have rated Southwest at 7.9/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
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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.

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