DCA - MDW

$89 Find Cheap Flights from Reagan Washington National Airport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Reagan-National to Midway departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$177
Overall average: $312
Delta
Sat 3/7Sat 3/14
DCA - MDW • 1 stop
Cheapest non-stop
$205
Typical prices: $259-$418
Southwest
Sat 4/11Tue 4/14
DCA - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
DCA is easily accessible via the city's metro line.
The CTA Orange Line connects MDW to downtown quickly.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $177 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 20% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Reagan-National to Midway (DCA-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Reagan-National to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Reagan-National to Midway

Sat, Mar 7 - Sat, Mar 14
Delta Logo
6:03 am - 8:54 am
DCA
-
MDW
3h 51m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$177Delta
Sat, Mar 7 - Tue, Mar 10
Delta Logo
6:03 am - 8:54 am
DCA
-
MDW
3h 51m
1 stop
Delta Logo
6:07 pm - 11:39 pm
MDW
-
DCA
4h 32m
1 stop
$197Delta
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
1:30 pm - 4:15 pm
MDW
-
DCA
1h 45mnonstop
$205Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
6:10 am - 10:25 am
DCA
-
MDW
5h 15m
1 stop
Southwest Logo
4:20 pm - 7:10 pm
MDW
-
DCA
1h 50mnonstop
$207Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
6:35 pm - 9:30 pm
MDW
-
DCA
1h 55mnonstop
$213Southwest
Sat, Mar 7 - Wed, Mar 11
Delta Logo
6:03 am - 8:54 am
DCA
-
MDW
3h 51m
1 stop
Delta Logo
1:10 pm - 6:59 pm
MDW
-
DCA
4h 49m
1 stop
$214Delta
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
4:40 pm - 11:00 pm
MDW
-
DCA
5h 20m
1 stop
$215Southwest
Wed, Apr 1 - Wed, Apr 8
Delta Logo
6:00 am - 8:53 am
DCA
-
MDW
3h 53m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$217Delta
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
12:15 pm - 2:45 pm
DCA
-
MDW
3h 30m
1 stop
Southwest Logo
6:35 pm - 9:30 pm
MDW
-
DCA
1h 55mnonstop
$219Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
6:40 am - 7:45 am
DCA
-
MDW
2h 05mnonstop
Southwest Logo
10:10 am - 6:20 pm
MDW
-
DCA
7h 10m
2 stops
$220Southwest
Booking Insights

KAYAK's insights & trends for Reagan-National to Midway flights

Get data-powered insights and trends into flights from Reagan-National to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Chicago Midway Airport?

The average price of all round-trip flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Wednesday and more expensive on a Sunday. On your return trip to Reagan Washington National Airport, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport is July, where tickets cost $263 (return) on average. On the other hand, the most expensive months are November and January, where the average cost of round-trip tickets is $393 and $386 respectively.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $306 on average.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Reagan-National to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Ramsey Qubein

Ramsey Qubein

Expert on DCA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Good to know

Low seasonJanuary
Cheapest flight$89
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Reagan Washington National Airport to Chicago Midway Airport

When to book flights from Reagan-National to Midway

Are your dates flexible? Find out the best times to travel from Reagan-National to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Reagan Washington National Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport was $89 for a one-way ticket and $177 for a round-trip.

  • Do I need a passport to fly between Reagan Washington National Airport and Chicago Midway Airport?

    No

  • Which airports will I be using when flying from Reagan Washington National Airport to Chicago Midway Airport?

    When flying out of Reagan Washington National Airport you will be using Washington, D.C. Reagan-National. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Reagan Washington National Airport to Chicago Midway Airport?

    American Airlines, Alaska Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the Reagan Washington National Airport to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Reagan Washington National Airport to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Reagan Washington National Airport to Chicago Midway Airport flight route.

  • On which days can I fly direct from Reagan Washington National Airport to Chicago Midway Airport?

    There are nonstop flights from Reagan Washington National Airport to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Reagan Washington National Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Reagan Washington National Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Reagan Washington National Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Reagan Washington National Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Reagan Washington National Airport with another airline. Booking your flights between Reagan Washington National Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Reagan Washington National Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Reagan Washington National Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $169 or less one-way and $298 or less round-trip.

Prefer to fly direct from Reagan Washington National Airport to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Washington, D.C. Reagan-National to Chicago Midway.
Find which airlines fly direct from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Washington, D.C. Reagan-National to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Washington, D.C. Reagan-National

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Reagan-National to Midway

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Reagan-National to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4289 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Everything you need to know for your flight from Reagan-National to Midway

Information on your arrival and departure airports