Detroit (DTW) to Chicago (MDW) flights
2 airlines fly nonstop from Detroit (DTW) to Chicago (MDW): Delta Air Lines and Southwest Airlines. The two airports are 227 miles (365 km) apart. Delta Air Lines is in SkyTeam. There are also 24 ways to fly it with one stop, through Grand Rapids, Milwaukee and Indianapolis and more.
Airlines flying nonstop from DTW to MDW
- Delta Air LinesSkyTeam · bookable with 8 programsWho books it
- Southwest AirlinesNot in an allianceWho books it
Book DTW to MDW with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Aeromexico RewardsBooks Delta Air Lines
- Air France-KLM Flying BlueBooks Delta Air Lines
- China Eastern Eastern MilesBooks Delta Air Lines
- Delta SkyMilesBooks Delta Air Lines
- Garuda Indonesia GarudaMilesBooks Delta Air Lines
- Korean Air SKYPASSBooks Delta Air Lines
- SAS EuroBonusBooks Delta Air Lines
- Virgin Atlantic Flying ClubBooks Delta Air Lines
DTW to MDW with one stop
24 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Grand Rapids (GRR)Delta Air Lines, then Southwest Airlines
- Via Milwaukee (MKE)Delta Air Lines, then Southwest Airlines
- Via Indianapolis (IND)Delta Air Lines, then Southwest Airlines
- Via Cleveland (CLE)Delta Air Lines, then Southwest Airlines
- Via Columbus (CMH)Delta Air Lines, then Southwest Airlines
- Via Cincinnati (CVG)Delta Air Lines, then Southwest Airlines
- Via Louisville (SDF)Delta Air Lines, then Southwest Airlines
- Via Pittsburgh (PIT)Delta Air Lines, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Buffalo (BUF)Delta Air Lines and American Airlines, then Southwest Airlines
- Via Rochester (ROC)Delta Air Lines, then Southwest Airlines
- Via Des Moines (DSM)Delta Air Lines, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Knoxville (TYS)Delta Air Lines, then Allegiant Air
DTW to MDW: common questions
Which airlines fly nonstop from DTW to MDW?
Delta Air Lines (SkyTeam) and Southwest Airlines fly nonstop from Detroit (DTW) to Chicago (MDW).
How far is Detroit from Chicago by plane?
Detroit (DTW) and Chicago (MDW) are 227 miles (365 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book DTW to MDW award flights?
8 programs can book at least one of the nonstop airlines: Aeromexico Rewards, Air France-KLM Flying Blue, China Eastern Eastern Miles, Delta SkyMiles, Garuda Indonesia GarudaMiles, Korean Air SKYPASS, SAS EuroBonus and Virgin Atlantic Flying Club. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does DTW to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for DTW to MDW with taxes and fees.
Where can I connect between Detroit and Chicago?
The most direct connections are through Grand Rapids (GRR), Milwaukee (MKE), Indianapolis (IND), Cleveland (CLE) and Columbus (CMH). On 4 of them the same airline flies both flights, for example Southwest Airlines through Saint Louis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.