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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 6/16. 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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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
6:00 am - 12:05 pm
DCA
-
MDW
7h 05m
2 stops
Southwest Logo
2:50 pm - 9:55 pm
MDW
-
DCA
6h 05m
1 stop
$233Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
6:50 pm - 9:55 pm
DCA
-
MDW
4h 05m
1 stop
Southwest Logo
8:50 am - 3:50 pm
MDW
-
DCA
6h 00m
2 stops
$236Southwest
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
9:30 pm - 10:30 pm
DCA
-
MDW
2h 00mnonstop
Southwest Logo
8:15 am - 11:10 am
MDW
-
DCA
1h 55mnonstop
$237Southwest
Tue, Jun 23 - Thu, Jun 25
Delta Logo
6:00 am - 9:53 am
DCA
-
MDW
4h 53m
1 stop
Delta Logo
5:10 pm - 11:43 pm
MDW
-
DCA
5h 33m
1 stop
$238Delta
Wed, Sep 16 - Mon, Sep 21
Southwest Logo
7:25 am - 8:20 am
DCA
-
MDW
1h 55mnonstop
Southwest Logo
1:20 pm - 4:15 pm
MDW
-
DCA
1h 55mnonstop
$239Southwest
Thu, Sep 24 - Sat, Sep 26
Southwest Logo
11:40 am - 5:55 pm
DCA
-
MDW
7h 15m
2 stops
Southwest Logo
5:55 am - 8:40 am
MDW
-
DCA
1h 45mnonstop
$242Southwest
Tue, Jun 23 - Sat, Jun 27
Southwest Logo
9:00 pm - 10:00 pm
DCA
-
MDW
2h 00mnonstop
Southwest Logo
5:40 am - 8:25 am
MDW
-
DCA
1h 45mnonstop
$243Southwest
Thu, Jul 2 - Tue, Jul 7
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
Southwest Logo
12:00 pm - 1:00 pm
DCA
-
MDW
2h 00mnonstop
Southwest Logo
11:50 am - 6:55 pm
MDW
-
DCA
6h 05m
1 stop
$247Southwest
Mon, Jul 13 - Wed, Jul 15
Delta Logo
6:00 am - 9:14 am
DCA
-
MDW
4h 14m
1 stop
Delta Logo
1:18 pm - 6:59 pm
MDW
-
DCA
4h 41m
1 stop
$248Delta
Wed, Jul 1 - Tue, Jul 7

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
Jul 1
DCA6:00 amWashington, D.C. Reagan-National
4h 14m
1 stop
MDW9:14 amChicago Midway
Jul 7
MDW1:18 pmChicago Midway
4h 41m
1 stop
DCA6:59 pmWashington, D.C. Reagan-National
$248
Delta
Jun 16
DCA9:39 amWashington, D.C. Reagan-National
4h 07m
1 stop
MDW12:46 pmChicago Midway
Jun 23
MDW1:26 pmChicago Midway
8h 33m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$260
Delta
Aug 6
DCA6:10 amWashington, D.C. Reagan-National
4h 07m
1 stop
MDW9:17 amChicago Midway
Aug 6
MDW6:42 pmChicago Midway
3h 17m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$265

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
Aug 18
DCA6:00 amWashington, D.C. Reagan-National
7h 05m
2 stops
MDW12:05 pmChicago Midway
Aug 20
MDW2:50 pmChicago Midway
6h 05m
1 stop
DCA9:55 pmWashington, D.C. Reagan-National
$233
Southwest
Aug 6
DCA6:50 pmWashington, D.C. Reagan-National
4h 05m
1 stop
MDW9:55 pmChicago Midway
Aug 11
MDW8:50 amChicago Midway
6h 00m
2 stops
DCA3:50 pmWashington, D.C. Reagan-National
$236
Southwest
Jun 23
DCA3:00 pmWashington, D.C. Reagan-National
5h 05m
1 stop
MDW7:05 pmChicago Midway
Jun 27
MDW5:05 pmChicago Midway
1h 50m
DCA7:55 pmWashington, D.C. Reagan-National
$237

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 May 27, 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

Tue 8/18

6:00 am-12:05 pm

2 stops7h 05m

Chicago Midway

Thu 8/20

2:50 pm-9:55 pm

1 stop6h 05m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/6

6:50 pm-9:55 pm

1 stop4h 05m

Chicago Midway

Tue 8/11

8:50 am-3:50 pm

2 stops6h 00m

$236

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/23

9:30 pm-10:30 pm

Nonstop2h 00m

Chicago Midway

Thu 6/25

8:15 am-11:10 am

Nonstop1h 55m

$237

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/16

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

Mon 9/21

5:10 pm-11:43 pm

1 stop5h 33m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/24

7:25 am-8:20 am

Nonstop1h 55m

Chicago Midway

Sat 9/26

1:20 pm-4:15 pm

Nonstop1h 55m

$239

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/23

11:40 am-5:55 pm

2 stops7h 15m

Chicago Midway

Sat 6/27

5:55 am-8:40 am

Nonstop1h 45m

$242
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 7/2

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

Tue 7/7

5:40 am-8:25 am

Nonstop1h 45m

$243

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

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 7/13

12:00 pm-1:00 pm

Nonstop2h 00m

Chicago Midway

Wed 7/15

11:50 am-6:55 pm

1 stop6h 05m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 7/1

6:00 am-9:14 am

1 stop4h 14m

Chicago Midway

Tue 7/7

1:18 pm-6:59 pm

1 stop4h 41m

$248

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 $262. 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 July is also very affordable. Most momondo users find prices during this month for around $266.

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 $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, 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 $405.

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 $327 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $373. 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 $334 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 $206 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 May 2026, prices for Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights are approximately 25% 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

$205

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 $205. 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 $320.
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 $204Free CancellationRating
7.9
4,265 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 33 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 $204 round-trip, up to an average price of $343. 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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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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