Flight Routes from Chicago Midway to San Juan (Puerto Rico)

Compare cheap outbound and return flights from Chicago Midway (MDW) to San Juan (Puerto Rico) (SJU) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€517
Fastest outbound flight
Fastest inbound flight
non-stop flights
3x / week
Flight distance
3,317 km
Time difference

Cheap flight offers from Chicago Midway to San Juan Puerto Rico

sorted by price and recency
  1. –
    Volaris
    –
    MDW–SJU
    3 stopovers
    United Airlines
    –
    SJU–MDW
    3 stopovers
    €1,225
  2. –
    Frontier Airlines
    –
    MDW–SJU
    1 stopover
    Frontier Airlines
    –
    SJU–MDW
    1 stopover
    €517

Flight schedule from Chicago Midway (MDW) to San Juan (Puerto Rico) (SJU)

Select a travel date in the flight schedule for the route from Chicago Midway (MDW) to San Juan (Puerto Rico) (SJU) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsMDW–SJU · 1 of 1
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. MDWSJU
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Chicago Midway and San Juan (Puerto Rico)

      Departure airport Airport Chicago Midway International Airport, IL (MDW)
      Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
      Destination country Flights to Puerto Rico
      City-Code - Arrival airport Chicago - San Juan - Luis Muñoz Marín International Airport
      Departure airport - Destination country Chicago Midway International Airport, IL - Puerto Rico
      Alternative flights to San Juan (Puerto Rico)
      Flight destinations with a similar price
      Flight destinations with a similar price