Chicago (MDW) to Cancun (CUN) flights
One airline flies nonstop from Chicago (MDW) to Cancun (CUN): 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 MDW to CUN
- Southwest AirlinesNot in an allianceWho books it
MDW to CUN 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)Southwest Airlines, then Delta Air Lines, Frontier Airlines and 2 more+1
- Via Tampa (TPA)Southwest Airlines, then JetBlue Airways and Breeze Airways
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Orlando (MCO)Southwest Airlines and Frontier Airlines the whole way
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Charlotte (CLT)Southwest Airlines, then American Airlines
- Via Charleston (CHS)Southwest Airlines, then Breeze Airways
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Miami (MIA)Southwest Airlines, then American Airlines, LATAM Airlines and 1 more
- Via Fort Lauderdale (FLL)Southwest Airlines, then JetBlue Airways
MDW to CUN: common questions
Which airlines fly nonstop from MDW to CUN?
Southwest Airlines flies nonstop from Chicago (MDW) to Cancun (CUN).
How far is Chicago from Cancun by plane?
Chicago (MDW) and Cancun (CUN) 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 MDW to CUN cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to CUN with taxes and fees.
Where can I connect between Chicago and Cancun?
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.