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Cheap flights from Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Chicago departing on 8/11. 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
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
9:15 pm - 10:10 pm
DCA
-
MDW
1h 55mnonstop
Southwest Logo
5:10 pm - 8:05 pm
MDW
-
DCA
1h 55mnonstop
$241Southwest
Thu, Sep 3 - Sat, Sep 5
Southwest Logo
10:45 am - 3:00 pm
DCA
-
MDW
5h 15m
1 stop
Southwest Logo
5:50 pm - 10:50 pm
MDW
-
DCA
4h 00m
1 stop
$242Southwest
Fri, Oct 2 - Mon, Oct 5
Southwest Logo
6:40 pm - 7:35 pm
DCA
-
MDW
1h 55mnonstop
Southwest Logo
5:45 am - 8:30 am
MDW
-
DCA
1h 45mnonstop
$243Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
11:40 am - 4:20 pm
DCA
-
MDW
5h 40m
1 stop
Southwest Logo
8:15 am - 3:50 pm
MDW
-
DCA
6h 35m
2 stops
$244Southwest
Tue, Aug 11 - Fri, Aug 21
Southwest Logo
3:30 pm - 7:20 pm
DCA
-
MDW
4h 50m
1 stop
Southwest Logo
8:50 am - 3:50 pm
MDW
-
DCA
6h 00m
2 stops
$245Southwest
Fri, Aug 14 - Tue, Aug 18
Southwest Logo
12:15 pm - 3:25 pm
DCA
-
MDW
4h 10m
1 stop
Southwest Logo
7:50 am - 3:55 pm
MDW
-
DCA
7h 05m
2 stops
$247Southwest
Fri, Aug 28 - Sat, Aug 29
Southwest Logo
12:45 pm - 5:00 pm
DCA
-
MDW
5h 15m
1 stop
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$249Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
1:20 pm - 4:40 pm
DCA
-
MDW
4h 20m
1 stop
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$251Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$252Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
5:05 pm - 10:40 pm
DCA
-
MDW
6h 35m
1 stop
Southwest Logo
5:45 am - 8:30 am
MDW
-
DCA
1h 45mnonstop
$253Southwest
Fri, Sep 4 - Mon, Sep 7

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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
Sep 3
DCA9:15 pmWashington, D.C. Reagan-National
1h 55m
MDW10:10 pmChicago Midway
Sep 5
MDW5:10 pmChicago Midway
1h 55m
DCA8:05 pmWashington, D.C. Reagan-National
$241
Southwest
Oct 2
DCA10:45 amWashington, D.C. Reagan-National
5h 15m
1 stop
MDW3:00 pmChicago Midway
Oct 5
MDW5:50 pmChicago Midway
4h 00m
1 stop
DCA10:50 pmWashington, D.C. Reagan-National
$242
Southwest
Sep 4
DCA6:40 pmWashington, D.C. Reagan-National
1h 55m
MDW7:35 pmChicago Midway
Sep 7
MDW5:45 amChicago Midway
1h 45m
DCA8:30 amWashington, D.C. Reagan-National
$243

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
Aug 21
DCA6:30 pmWashington, D.C. Reagan-National
5h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 28
MDW12:46 pmChicago Midway
4h 47m
1 stop
DCA6:33 pmWashington, D.C. Reagan-National
$257
Delta
Aug 14
DCA6:10 amWashington, D.C. Reagan-National
4h 07m
1 stop
MDW9:17 amChicago Midway
Aug 17
MDW5:10 pmChicago Midway
5h 38m
1 stop
DCA11:48 pmWashington, D.C. Reagan-National
$265
Delta
Aug 6
DCA6:59 amWashington, D.C. Reagan-National
5h 52m
1 stop
MDW11:51 amChicago Midway
Aug 11
MDW6:05 amChicago Midway
4h 22m
1 stop
DCA11:27 amWashington, D.C. Reagan-National
$280

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 July 12, 2026.
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

Cheapest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/3

9:15 pm-10:10 pm

Nonstop1h 55m

Chicago Midway

Sat 9/5

5:10 pm-8:05 pm

Nonstop1h 55m

$241

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 10/2

10:45 am-3:00 pm

1 stop5h 15m

Chicago Midway

Mon 10/5

5:50 pm-10:50 pm

1 stop4h 00m

$242
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 9/4

6:40 pm-7:35 pm

Nonstop1h 55m

Chicago Midway

Mon 9/7

5:45 am-8:30 am

Nonstop1h 45m

$243

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 8/11

11:40 am-4:20 pm

1 stop5h 40m

Chicago Midway

Fri 8/21

8:15 am-3:50 pm

2 stops6h 35m

$244

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 8/14

3:30 pm-7:20 pm

1 stop4h 50m

Chicago Midway

Tue 8/18

8:50 am-3:50 pm

2 stops6h 00m

$245

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 8/28

12:15 pm-3:25 pm

1 stop4h 10m

Chicago Midway

Sat 8/29

7:50 am-3:55 pm

2 stops7h 05m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/8

12:45 pm-5:00 pm

1 stop5h 15m

Chicago Midway

Mon 8/10

9:00 pm-11:55 pm

Nonstop1h 55m

$249

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/5

1:20 pm-4:40 pm

1 stop4h 20m

Chicago Midway

Mon 9/7

9:00 pm-11:55 pm

Nonstop1h 55m

$251

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/13

1:00 pm-5:50 pm

2 stops5h 50m

Chicago Midway

Mon 8/17

9:00 pm-11:55 pm

Nonstop1h 55m

$252

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 9/4

5:05 pm-10:40 pm

1 stop6h 35m

Chicago Midway

Mon 9/7

5:45 am-8:30 am

Nonstop1h 45m

$253

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?

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

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Reagan-National Airport, with most prices found around $280. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Washington, D.C. Reagan-National Airport during the month August is also very affordable. Most momondo users find prices during this month for around $303.

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 $334. 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 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 $416.

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 $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $378. 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 $362 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 $250 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?

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?

As of July 2026, prices for Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights are approximately 15% 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

$189

Fastest flight time

1h 55m

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 $189. 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 $297.
The fastest flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport takes 1h 55m
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 1h 55m.

  • 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 $217Free CancellationRating
7.9
4,251 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 32 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 $217 round-trip, up to an average price of $362. Our users have rated Southwest at 7.9/10.

Traveling to a place near Chicago?

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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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