Flight Routes from Detroit to Chicago Midway

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

Trip type
Cheapest roundtrip flight
from€264
Fastest flight
non-stop flights
64x / week
Flight distance
367 km
Time difference

Cheap flight offers from Detroit to Chicago Midway

sorted by price and recency
filters
  1. –
    Volaris
    –
    DTW–MDW
    2 stopovers
    Aeroméxico
    –
    MDW–DTW
    3 stopovers
    €1,667
  2. –
    Southwest Airlines
    –
    DTW–MDW
    non-stop flight
    Southwest Airlines
    –
    MDW–DTW
    non-stop flight
    €264

Flight schedule from Detroit (DTW) to Chicago Midway (MDW)

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

offers
Active filtersnone
Matching outbound flightsDTW–MDW · 12 of 12
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. DTWMDW
      nonstop
      1. Southwest Airlines
    2. DTWMDW
      nonstop
      1. Southwest Airlines
    3. DTWMDW
      nonstop
      1. Southwest Airlines
    4. DTWMDW
      nonstop
      1. Delta Air Lines
    5. DTWMDW
      nonstop
      1. Delta Air Lines
    6. DTWMDW
      nonstop
      1. Delta Air Lines
    7. DTWMDW
      nonstop
      1. Southwest Airlines
    8. DTWMDW
      nonstop
      1. Southwest Airlines
    9. DTWMDW
      nonstop
      1. Delta Air Lines
    10. DTWMDW
      nonstop
      1. Southwest Airlines
    11. DTWMDW
      nonstop
      1. Southwest Airlines
    12. DTWMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Detroit and Chicago Midway

      Departure airport Airport Detroit Metropolitan Wayne County Airport, MI (DTW)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      City-Code - Arrival airport Detroit Metropolitan Area - Chicago Midway International Airport, IL
      Departure airport - Destination country Detroit Metropolitan Wayne County Airport, MI - United States
      Departure airport - City-Code Detroit Metropolitan Wayne County Airport, MI - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway
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