Chicago to Cancún (MDW–CUN) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
MDW–CUN is served by 2 airlines with nonstop service. Southwest Airlines and Frontier lead the route. The flight covers 1,434 miles in approximately 3h 30m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 19 | 737, 738, 7S7 | 3h29-3h35 | – | – | |
| F9 Frontier Also: Y4 | 0 | – | – | – | Y4 |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Cancún from Chicago
| Metric | MDW→CUN | ORD→CUN | RFD→CUN |
|---|---|---|---|
| Distance from MDW | – | 15 mi | 75 mi |
| Nonstop airlines | 2 | 7 | 1 |
| Weekly flights | 19 | 58 | – |
| Flight time | 3h 30m | 3h 22m | 3h 39m |
| Departure OTP | 72% | – | – |
Travel Essentials
MDW: CDT · CUN: EST
When it's 6:00 PM in Chicago, it's 6:00 PM in Cancún.
US citizens enter Mexico visa-free for up to 180 days for tourism. Complete the immigration form (FMM) online or on arrival; the online version speeds up processing. Passport must be valid for the duration of stay.
Duty-free allowances: USD 500 in goods. Mexico prohibits importing certain foods and medications without documentation. Declare cash over USD 10,000.
Authorised airport taxis operate from a voucher desk inside each terminal. Fares to the Hotel Zone run MXN 350–550 (USD $17–28) and to downtown Cancún MXN 200–300. Purchase tickets inside before exiting to avoid touts. ADO buses depart from outside Terminal 2 to downtown Cancún for MXN 102 and continue to Playa del Carmen and Tulum.The Tren Maya connects Terminal 4 to Playa del Carmen, Tulum, and the broader Yucatán Peninsula. Car rental desks are located in all terminals; driving is straightforward on Highway 307.
Tropical climate with two distinct seasons. Dry season (December–April) brings warm, sunny weather at 25–32°C with low humidity, the peak tourist season and most reliable flying conditions. Wet season (May–November) is hot, humid, and prone to heavy afternoon downpours; thunderstorms can cause short ground delays.
Hurricane season runs June through November, peaking in September–October. Major storms (e.g., Wilma 2005, Zeta 2020) can close the airport for 12–48 hours. Monitor forecasts carefully from August through October. September is statistically the highest-risk month.
MDW–CUN Quick Facts
Frequently Asked Questions
Flights from MDW to CUN
Chicago Midway International Airport (MDW) and Cancún International Airport (CUN) are connected by nonstop service from Southwest Airlines and Frontier. With 19 weekly departures, this is a well served route.
MDW to CUN Flight Duration and Schedule
Nonstop flight time from MDW to CUN is about 3 hours 30 minutes gate to gate. The route covers a distance of 1,434 miles (2,308 km). There are approximately 19 weekly flights outbound and 13 return, totaling 32 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via St. Louis Lambert, Hartsfield Jackson Atlanta and Orlando. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), Chicago/Rockford (RFD) and Milwaukee (MKE).