Des Moines (DSM) to Chicago (MDW) flights
One airline flies nonstop from Des Moines (DSM) to Chicago (MDW): Southwest Airlines. The two airports are 305 miles (491 km) apart. There are also 3 ways to fly it with one stop, through Minneapolis, Detroit and Nashville.
Airlines flying nonstop from DSM to MDW
- Southwest AirlinesNot in an allianceWho books it
DSM to MDW with one stop
3 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
DSM to MDW: common questions
Which airlines fly nonstop from DSM to MDW?
Southwest Airlines flies nonstop from Des Moines (DSM) to Chicago (MDW).
How far is Des Moines from Chicago by plane?
Des Moines (DSM) and Chicago (MDW) are 305 miles (491 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does DSM 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 DSM to MDW with taxes and fees.
Where can I connect between Des Moines and Chicago?
The most direct connections are through Minneapolis (MSP), Detroit (DTW) and Nashville (BNA). On 3 of them the same airline flies both flights, for example Delta Air Lines through Minneapolis.
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.