Flight Routes from Boston to Chicago Midway

Trip type

Our cheapest offers for flights from Boston to Chicago Midway

Here you can compare cheap flights from Boston (BOS) to Chicago Midway (MDW) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago Midway. Prices and availability may change at any time.

Flight schedule from Boston (BOS) to Chicago Midway (MDW)

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

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Matching outbound flights18 of 18
fromto
dep.arr.
durationstopovers
  1. August 23 – 29, 2026
  2. Aug 30 – Sep 5, 2026
  3. September 6 – 12, 2026
    1. BOSMDW
      nonstop
      1. Southwest Airlines
    2. BOSMDW
      nonstop
      1. Southwest Airlines
    3. BOSMDW
      nonstop
      1. Southwest Airlines
    4. BOSMDW
      nonstop
      1. Southwest Airlines
    5. BOSMDW
      nonstop
      1. Southwest Airlines
    6. BOSMDW
      nonstop
      1. Southwest Airlines
    7. BOSMDW
      nonstop
      1. Southwest Airlines
    8. BOSMDW
      nonstop
      1. Southwest Airlines
    9. BOSMDW
      1 stopover
      1. Delta Air Lines
    10. BOSMDW
      nonstop
      1. Southwest Airlines
    11. BOSMDW
      nonstop
      1. Southwest Airlines
    12. BOSMDW
      nonstop
      1. Southwest Airlines
    13. BOSMDW
      nonstop
      1. Southwest Airlines
    14. BOSMDW
      nonstop
      1. Southwest Airlines
    15. BOSMDW
      nonstop
      1. Southwest Airlines

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

      Favorite airline: Frontier Airlines
      The most popular airline for flights from Boston to Chicago Midway is Frontier Airlines.
      Frontier Airlines
      52 %
      Delta
      24 %
      Porter Airlines
      16 %
      Cheapest weekday: Thursday
      The cheapest days to fly on this route are Thursday.
      Favourite connection: via Orlando
      37 % of booked tickets on this route are for flights with a transfer in Orlando.
      Route
      bookings
      1 stopover Orlando International Airport, FL
      25h 34min, from 396 $
      37 %
      1 stopover Philadelphia International Airport, PA
      05h 45min, from 217 $
      32 %
      1 stopover Toronto - City Centre Airport
      10h 17min, from 550 $
      21 %

      Flight information: Boston - Chicago Midway

      Roundtrip from 413,00 $
      Flight duration min. 02:45 / max. 06:55
      Return flight duration min. 02:10/ max. 11:15
      Distance 1383 km
      Flights per week 23
      Departure airport Airport Boston Logan International Airport, MA (BOS)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Boston Logan International Airport, MA - United States
      Departure airport - City-Code Boston Logan International Airport, MA - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway
      Flight destinations with a similar price