$99 Find Cheap Flights from Reagan Washington National Airport to Chicago Midway Airport - Compare and Save

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

The cheapest month for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport is September, where tickets cost $280 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $478 and $423 respectively.

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 $328 on average.

To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should book around 5 weeks before departure, which saves you about 60% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

In the past 5 days, the cheapest round-trip tickets from Reagan Washington National Airport to Chicago Midway Airport were found on Southwest ($245) and Delta ($276).

There is just one airline that flies from Washington, D.C. Reagan-National Airport to Chicago Midway Airport direct and that is Southwest. The best round-trip deal found from Southwest for the route is $217.

Detroit (DTW) is the top choice – 40% of KAYAK users who clicked on 1-stop flights from Reagan Washington National Airport to Chicago Midway Airport picked an itinerary connecting there.

Flights via Detroit (DTW) offer the most affordable fares, with an average round-trip price of $457.

Consider flying via Detroit (DTW) for the shortest journey. The average one-way travel time for flights connecting there is 3h 44m.

If you prefer a quick connection, Detroit (DTW) often has the shortest layovers from Reagan Washington National Airport to Chicago Midway Airport, with an average of 0h 49m.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are between 5 and 6 nonstop flights that take off from Washington, D.C. Reagan-National Airport and land in Chicago Midway Airport, with an average flight time of 2h 00m. The most common departure time is 9:00 pm and most flights take off in the morning. Each week, there are 41 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.