$114 Find Cheap Flights from Reagan Washington National Airport to Chicago Midway Airport - Compare and Save

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 8:07 am
• Latest: departs at 9:35 pm and lands at 11:42 pm.

The flight takes about 2h 07m.

Two cabin classes are available on flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport:

• Economy Class
• First Class

A nonstop flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport takes 2h 07m, 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.

Round-trip flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport range from $278 to $440, with an average of $333 over the past 12 months. Anything below $278 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 77% above the $333 route average. Book 25 weeks before departure for the lowest fares.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $333 round-trip, compared to $389 via a layover through Columbus (CMH).

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.

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%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $228 to $1,448. That means the highest observed fare was about 6x higher than the lowest one.

JetBlue is the only airline on the Washington, D.C. Reagan-National Airport to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

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 $120, which is 47% below the typical average for this route.

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

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).

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

• Detroit Metropolitan Wayne County (DTW) - 50% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 13% of one-stop connections
• Columbus (CMH) - 13% of one-stop connections
• Minneapolis St Paul (MSP) - 13% of one-stop connections

Yes. Flexible dates can save you up to 20% on flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport. Tuesday is the cheapest departure day at $299 round-trip on average, while Monday is the most expensive at $371, a difference of $72.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 49m, 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.

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

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.

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
• JetBlue: a cabin bag in Economy Class class

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