Cancun (CUN) to Chicago (MDW) flights
One airline flies nonstop from Cancun (CUN) to Chicago (MDW): Southwest Airlines. The two airports are 1,434 miles (2,308 km) apart. There are also 37 ways to fly it with one stop, through Nashville, Indianapolis and Atlanta and more.
Airlines flying nonstop from CUN to MDW
- Southwest AirlinesNot in an allianceWho books it
CUN to MDW with one stop
37 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines, Southwest Airlines and 1 more the whole way
- Via New Orleans (MSY)Southwest Airlines the whole way
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Cincinnati (CVG)Delta Air Lines, Frontier Airlines and 2 more, then Southwest Airlines+1
- Via Tampa (TPA)JetBlue Airways and Breeze Airways, then Southwest Airlines
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Orlando (MCO)Frontier Airlines and Southwest Airlines the whole way
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Charleston (CHS)Breeze Airways, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Miami (MIA)American Airlines, LATAM Airlines and 1 more, then Southwest Airlines
- Via Fort Lauderdale (FLL)JetBlue Airways, then Southwest Airlines
CUN to MDW: common questions
Which airlines fly nonstop from CUN to MDW?
Southwest Airlines flies nonstop from Cancun (CUN) to Chicago (MDW).
How far is Cancun from Chicago by plane?
Cancun (CUN) and Chicago (MDW) are 1,434 miles (2,308 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does CUN 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 CUN to MDW with taxes and fees.
Where can I connect between Cancun and Chicago?
The most direct connections are through Nashville (BNA), Indianapolis (IND), Atlanta (ATL), New Orleans (MSY) and Saint Louis (STL). On 23 of them the same airline flies both flights, for example Southwest Airlines through Nashville.
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.