Flight Routes from Washington DC to Chicago Midway

Compare cheap outbound and return flights from Washington DC (DCA) to Chicago Midway (MDW) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
82x / week
Flight distance
965 km
Time difference

Flight schedule from Washington DC (DCA) to Chicago Midway (MDW)

Select a travel date in the flight schedule for the route from Washington DC (DCA) to Chicago Midway (MDW) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flights18 of 18
fromto
dep.arr.
durationstopovers
  1. September 6 – 12, 2026
  2. September 13 – 19, 2026
  3. September 20 – 26, 2026
    1. DCAMDW
      nonstop
      1. Southwest Airlines
    2. DCAMDW
      nonstop
      1. Southwest Airlines
    3. DCAMDW
      nonstop
      1. Southwest Airlines
    4. DCAMDW
      nonstop
      1. Southwest Airlines
    5. DCAMDW
      nonstop
      1. Southwest Airlines
    6. DCAMDW
      nonstop
      1. Southwest Airlines
    7. DCAMDW
      nonstop
      1. Southwest Airlines
    8. DCAMDW
      nonstop
      1. Southwest Airlines
    9. DCAMDW
      nonstop
      1. Southwest Airlines
    10. DCAMDW
      nonstop
      1. Southwest Airlines
    11. DCAMDW
      nonstop
      1. Southwest Airlines
    12. DCAMDW
      nonstop
      1. Southwest Airlines
    13. DCAMDW
      nonstop
      1. Southwest Airlines
    14. DCAMDW
      nonstop
      1. Southwest Airlines
    15. DCAMDW
      nonstop
      1. Southwest Airlines

      Tips and tricks to help you find cheap flights from Washington DC to Chicago Midway

      Favorite airline: Frontier Airlines
      65 % of flights from Washington DC to Chicago Midway are booked with Frontier Airlines.
      Frontier Airlines
      65 %
      Delta
      35 %
      Favourite connection: via Denver
      On this route, flights with a stopover in Denver are the most popular.
      Route
      bookings
      1 stopover Denver International Airport, CO
      09h 54min, from 413 US$
      65 %
      1 stopover Detroit Metropolitan Wayne County Airport, MI
      03h 50min, from 182 US$
      29 %
      1 stopover Hartsfield-Jackson Atlanta International Airport, GA
      06h 19min, from 566 US$
      6 %

      Important flight information

      Discover more flights around Washington DC and Chicago Midway

      Departure airport Airport Washington DC - Ronald Reagan National Airport, VA (DCA)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      City-Code - Arrival airport Washington-DC - Chicago Midway International Airport, IL
      Departure airport - Destination country Washington DC - Ronald Reagan National Airport, VA - United States
      Departure airport - City-Code Washington DC - Ronald Reagan National Airport, VA - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway