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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $88

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 9/5. 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

Frontier Logo
1:00 pm - 3:53 pmDCA-MDW
27h 53m1 stop
Frontier Logo
4:48 pm - 4:59 pmMDW-DCA
23h 11m1 stop
$177Frontier
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
6:05 am - 7:00 amDCA-MDW
1h 55mnonstop
Southwest Logo
10:05 am - 12:55 pmMDW-DCA
1h 50mnonstop
$189Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 3
Southwest Logo
3:30 pm - 4:30 pmDCA-MDW
2h 00mnonstop
Southwest Logo
6:10 am - 12:00 pmMDW-DCA
4h 50m1 stop
$199Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 29
Southwest Logo
3:15 pm - 4:25 pmDCA-MDW
2h 10mnonstop
Southwest Logo
5:30 pm - 8:25 pmMDW-DCA
1h 55mnonstop
$203Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
Delta Logo
6:15 pm - 10:57 pmMDW-DCA
3h 42m1 stop
$209Delta
Find Deal
Tue, Sep 16 - Wed, Sep 17
Southwest Logo
9:00 am - 10:00 amDCA-MDW
2h 00mnonstop
Southwest Logo
3:35 pm - 11:15 pmMDW-DCA
6h 40m1 stop
$213Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 3
Southwest Logo
6:00 am - 6:55 amDCA-MDW
1h 55mnonstop
Southwest Logo
10:05 am - 12:55 pmMDW-DCA
1h 50mnonstop
$217Southwest
Find Deal
Thu, Sep 25 - Sat, Sep 27
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
Delta Logo
6:00 am - 11:29 amMDW-DCA
4h 29m1 stop
$223Delta
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
4:10 pm - 9:12 pmDCA-MDW
6h 02m1 stop
Delta Logo
6:17 pm - 10:59 pmMDW-DCA
3h 42m1 stop
$233Delta
Find Deal
Sat, Aug 30 - Wed, Sep 3
Frontier Logo
7:00 am - 3:53 pmDCA-MDW
9h 53m1 stop
Frontier Logo
4:48 pm - 9:59 pmMDW-DCA
28h 11m1 stop
$253Frontier
Find Deal
Fri, Sep 26 - Mon, Sep 29

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
DCA6:05 amWashington, D.C. Reagan-National
1h 55m
MDW7:00 amChicago Midway
Sep 3
MDW10:05 amChicago Midway
1h 50m
DCA12:55 pmWashington, D.C. Reagan-National
$189
Find similar
Southwest
Oct 15
DCA3:30 pmWashington, D.C. Reagan-National
2h 00m
MDW4:30 pmChicago Midway
Oct 29
MDW6:10 amChicago Midway
4h 50m
1 stop
DCA12:00 pmWashington, D.C. Reagan-National
$199
Find similar
Southwest
Sep 3
DCA3:15 pmWashington, D.C. Reagan-National
2h 10m
MDW4:25 pmChicago Midway
Sep 6
MDW5:30 pmChicago Midway
1h 55m
DCA8:25 pmWashington, D.C. Reagan-National
$203
Find similar

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
Sep 16
DCA6:00 amWashington, D.C. Reagan-National
3h 40m
1 stop
MDW8:40 amChicago Midway
Sep 17
MDW6:15 pmChicago Midway
3h 42m
1 stop
DCA10:57 pmWashington, D.C. Reagan-National
$209
Find similar
Delta
Sep 13
DCA6:00 amWashington, D.C. Reagan-National
3h 40m
1 stop
MDW8:40 amChicago Midway
Sep 16
MDW6:00 amChicago Midway
4h 29m
1 stop
DCA11:29 amWashington, D.C. Reagan-National
$223
Find similar
Delta
Aug 30
DCA4:10 pmWashington, D.C. Reagan-National
6h 02m
1 stop
MDW9:12 pmChicago Midway
Sep 3
MDW6:17 pmChicago Midway
3h 42m
1 stop
DCA10:59 pmWashington, D.C. Reagan-National
$233
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 August 14, 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 9/4

1:00 pm-3:53 pm

1 stop27h 53m

Chicago Midway

Mon 9/8

4:48 pm-4:59 pm

1 stop23h 11m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/3

6:05 am-7:00 am

Nonstop1h 55m

Chicago Midway

Wed 9/3

10:05 am-12:55 pm

Nonstop1h 50m

$189

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 10/15

3:30 pm-4:30 pm

Nonstop2h 00m

Chicago Midway

Wed 10/29

6:10 am-12:00 pm

1 stop4h 50m

$199

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/3

3:15 pm-4:25 pm

Nonstop2h 10m

Chicago Midway

Sat 9/6

5:30 pm-8:25 pm

Nonstop1h 55m

$203

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 9/16

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Wed 9/17

6:15 pm-10:57 pm

1 stop3h 42m

$209

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/3

9:00 am-10:00 am

Nonstop2h 00m

Chicago Midway

Wed 9/3

3:35 pm-11:15 pm

1 stop6h 40m

$213

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/25

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sat 9/27

10:05 am-12:55 pm

Nonstop1h 50m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/13

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Tue 9/16

6:00 am-11:29 am

1 stop4h 29m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

4:10 pm-9:12 pm

1 stop6h 02m

Chicago Midway

Wed 9/3

6:17 pm-10:59 pm

1 stop3h 42m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 9/26

7:00 am-3:53 pm

1 stop9h 53m

Chicago Midway

Mon 9/29

4:48 pm-9:59 pm

1 stop28h 11m

$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 cheapest month to fly to Chicago Midway Airport?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Reagan-National Airport, with most prices found around $235. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Washington, D.C. Reagan-National Airport during the month January is also very affordable. Most momondo users find prices during this month for around $247.

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 $322. 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 $393.

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 $322 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $351. 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 $302 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 are 1 cabin classes 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.

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

$88

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 $88. 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 $177.
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

  • 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
FrontierPriceFrom $99Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
SouthwestPriceFrom $171Free CancellationRating
8.0
4,244 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 $171 round-trip, up to an average price of $297. 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
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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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