$89 Find Cheap Flights from Reagan Washington National Airport to Chicago Midway Airport - Compare and Save

Among airlines operating Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Washington, D.C. Reagan-National Airport and Chicago Midway Airport.

Flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport usually depart from Washington, D.C. Reagan-National (DCA) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $302 round-trip via Detroit Metropolitan Wayne County (DTW), compared to $328 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

One-stop flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 25% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 25% of one-stop connections
• Minneapolis St Paul (MSP) - 25% of one-stop connections
• Lambert-St Louis (STL) - 25% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 18% on the Washington, D.C. Reagan-National Airport to Chicago Midway Airport route. Tuesday is the cheapest departure day at $298 round-trip on average, while Monday is the most expensive at $360, a difference of $62. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 34%, evening flights for 16%, and night flights for 16%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Washington, D.C. Reagan-National Airport to Chicago Midway Airport:

• Earliest: departs at 6:00 am and lands at 8:02 am
• Latest: departs at 9:30 pm and lands at 11:32 pm.

The flight takes about 2h 02m.

Last-minute fares on this route - booked within 2 weeks of departure - run 77% above the route average of $328. Book 25 weeks before departure for the lowest fares.

A nonstop flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport takes 2h 02m, covering 599 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $177 to $1,520. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Washington, D.C. Reagan-National Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $91, which is 59% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 45m, compared with 4h 10m via Lambert-St Louis (STL) and 5h 17m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport is 1 hour behind Washington, D.C. Reagan-National Airport (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Round-trip flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport range from $274 to $426, with an average of $328 over the past 12 months. Anything below $274 counts as a good deal.