Flight Routes from Chicago Midway to Boston

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

Trip type
Fastest outbound flight
Fastest inbound flight
non-stop flights
23x / week
Flight distance
1,383 km
Time difference

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

Select a travel date in the flight schedule for the route from Chicago Midway (MDW) to Boston (BOS) 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. MDWBOS
      nonstop
      1. Southwest Airlines
    2. MDWBOS
      nonstop
      1. Southwest Airlines
    3. MDWBOS
      nonstop
      1. Southwest Airlines
    4. MDWBOS
      nonstop
      1. Southwest Airlines
    5. MDWBOS
      nonstop
      1. Southwest Airlines
    6. MDWBOS
      nonstop
      1. Southwest Airlines
    7. MDWBOS
      nonstop
      1. Southwest Airlines
    8. MDWBOS
      nonstop
      1. Southwest Airlines
    9. MDWBOS
      nonstop
      1. Southwest Airlines
    10. MDWBOS
      nonstop
      1. Southwest Airlines
    11. MDWBOS
      nonstop
      1. Southwest Airlines
    12. MDWBOS
      nonstop
      1. Southwest Airlines
    13. MDWBOS
      nonstop
      1. Southwest Airlines
    14. MDWBOS
      nonstop
      1. Southwest Airlines
    15. MDWBOS
      nonstop
      1. Southwest Airlines

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

      Favorite airline: Porter Airlines
      Flight tickets on the route Chicago Midway – Boston are most frequently booked with Porter Airlines.
      Porter Airlines
      57 %
      Delta
      43 %
      Favourite connection: via Toronto - City Centre
      On this route, flights with a stopover in Toronto - City Centre are the most popular.
      Route
      bookings
      1 stopover Toronto - City Centre Airport
      09h 12min, from 498 $
      57 %
      1 stopover Hartsfield-Jackson Atlanta International Airport, GA
      08h 11min, from 355 $
      29 %
      1 stopover Detroit Metropolitan Wayne County Airport, MI
      05h 44min, from 735 $
      14 %

      Important flight information

      Discover more flights around Chicago Midway and Boston

      Departure airport Airport Chicago Midway International Airport, IL (MDW)
      Arrival airport Airport Boston Logan International Airport, MA (BOS)
      Destination country Flights to United States
      City-Code - Arrival airport Chicago - Boston Logan International Airport, MA
      Departure airport - Destination country Chicago Midway International Airport, IL - United States
      Alternative flights to Boston
      Flight destinations with a similar price