Flight Routes from Boston to Chicago Midway

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

Trip type
Cheapest oneway flight
from€94
Cheapest roundtrip flight
from€563
Fastest outbound flight
Fastest inbound flight
non-stop flights
23x / week
Flight distance
1,383 km
Time difference

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.

offers
Active filtersnone
Matching outbound flightsBOS–MDW · 16 of 16
fromto
dep.arr.
durationstopovers
  1. Sep 27 – Oct 3, 2026
  2. October 4 – 10, 2026
  3. October 11 – 17, 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
      nonstop
      1. Southwest Airlines
    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 %

      Important flight information

      Discover more flights around Boston and Chicago Midway

      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
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