Denver (DEN) to Chicago (MDW) flights
One airline flies nonstop from Denver (DEN) to Chicago (MDW): Southwest Airlines. The two airports are 894 miles (1,439 km) apart. There are also 31 ways to fly it with one stop, through Omaha, Des Moines and Kansas City and more.
Airlines flying nonstop from DEN to MDW
- Southwest AirlinesNot in an allianceWho books it
DEN to MDW with one stop
31 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Omaha (OMA)Southwest Airlines the whole way
- Via Des Moines (DSM)Southwest Airlines the whole way
- Via Kansas City (MCI)Southwest Airlines the whole way+1
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Colorado Springs (COS)Southwest Airlines the whole way
- Via Wichita (ICT)Southwest Airlines the whole way
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines and Southwest Airlines the whole way
+2
- Via Tulsa (TUL)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Grand Rapids (GRR)Southwest Airlines the whole way
- Via Oklahoma City (OKC)Southwest Airlines the whole way
- Via Louisville (SDF)Southwest Airlines the whole way
- Via Cincinnati (CVG)Southwest Airlines the whole way
- Via Detroit (DTW)Delta Air Lines and Southwest Airlines the whole way+1
DEN to MDW: common questions
Which airlines fly nonstop from DEN to MDW?
Southwest Airlines flies nonstop from Denver (DEN) to Chicago (MDW).
How far is Denver from Chicago by plane?
Denver (DEN) and Chicago (MDW) are 894 miles (1,439 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does DEN 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 DEN to MDW with taxes and fees.
Where can I connect between Denver and Chicago?
The most direct connections are through Omaha (OMA), Des Moines (DSM), Kansas City (MCI), Milwaukee (MKE) and Colorado Springs (COS). On 31 of them the same airline flies both flights, for example Southwest Airlines through Omaha.
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.