Flights from Chicago to San Juan
Cheap MDW to San Juan flights
Book your MDW to SIG flights with Expedia and find last-minute Chicago to San Juan airfare. Expedia offers discount airfare on multiple airline carriers that fly direct and indirect routes between MDW and SIG, with new flight deals and promotions almost daily. When you book your next trip from Midway Intl. to Fernando Luis Ribas Dominicci with Expedia, you can rest assured you’re getting great ticket prices and excellent service from one of the world’s most trusted travel providers.
Discount flights from Chicago to San Juan airfare
Browse the best deals on flights from MDW to SIG. Deals are based on recent deals found by other Expedia users like you. Pricing may have changed for individual airlines. Expand the list to see all available flight deals from MDW to SIG.
| Carrier | Length of Stay | Travel Dates |
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Last Minute Chicago Flight Deals
Traveling on short notice? Expedia offers great deals on last-minute flights from Chicago Airport to the most popular destinations. Deals are based on recent prices found by other Expedia users within the last 12 hours. Prices change often for individual airlines, so check back regularly!
| This Weekend |
Next Weekend |
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Chicago, Illinois (MDW) to Puerto Rico Island, Puerto Rico (SIG)
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How This Works:
The calendar shows the best prices recently found by Expedia customers. Choose a departure date, then choose a return date to see your trip results.
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- Roundtrip (including all taxes and fees)
- Per Adult
- Based on e-ticket purchase
- Shown without coupon discounts
The lowest roundtrip price(s) recently found
Departing From:
| Airport | Flight To | Travel Dates (Nights) |
Hotel Rating | Package Discount |
Price per Passenger |
|---|---|---|---|---|---|
Popular Flights from Chicago, Illinois
Browse popular flight destinations from Chicago (MDW), and plan your next exciting trip. Expedia has cheap flights from Chicago on multiple airline carriers, so book your next trip today!
Top Chicago Flights to US Destinations
Chicago to Chicago (MDW - ORD)
Chicago to New York (MDW - JFK)
Chicago to Denver (MDW - DEN)
Chicago to Atlanta (MDW - ATL)
Chicago to San Francisco (MDW - SFO)
Chicago to Miami (MDW - MIA)
Chicago to Los Angeles (MDW - LAX)
Chicago to Las Vegas (MDW - LAS)
Chicago to Houston (MDW - IAH)
Chicago to Newark (MDW - EWR)
Chicago to New York (MDW - JFK)
Chicago to Denver (MDW - DEN)
Chicago to Atlanta (MDW - ATL)
Chicago to San Francisco (MDW - SFO)
Chicago to Miami (MDW - MIA)
Chicago to Los Angeles (MDW - LAX)
Chicago to Las Vegas (MDW - LAS)
Chicago to Houston (MDW - IAH)
Chicago to Newark (MDW - EWR)
Top Chicago International Destinations
Popular Flights from San Juan, Puerto Rico
Browse popular flight destinations from San Juan (SIG), and plan your next exciting trip. Expedia has cheap flights from San Juan on multiple airline carriers, so book your next trip today!
Top San Juan Flights to US Destinations
San Juan to Chicago (SIG - ORD)
San Juan to New York (SIG - JFK)
San Juan to Denver (SIG - DEN)
San Juan to Atlanta (SIG - ATL)
San Juan to San Francisco (SIG - SFO)
San Juan to Miami (SIG - MIA)
San Juan to Los Angeles (SIG - LAX)
San Juan to Las Vegas (SIG - LAS)
San Juan to Houston (SIG - IAH)
San Juan to Newark (SIG - EWR)
San Juan to New York (SIG - JFK)
San Juan to Denver (SIG - DEN)
San Juan to Atlanta (SIG - ATL)
San Juan to San Francisco (SIG - SFO)
San Juan to Miami (SIG - MIA)
San Juan to Los Angeles (SIG - LAX)
San Juan to Las Vegas (SIG - LAS)
San Juan to Houston (SIG - IAH)
San Juan to Newark (SIG - EWR)
Top San Juan International Destinations
San Juan to Chicago (SIG - ORD)
San Juan to New York (SIG - JFK)
San Juan to Denver (SIG - DEN)
San Juan to Atlanta (SIG - ATL)
San Juan to San Francisco (SIG - SFO)
San Juan to Miami (SIG - MIA)
San Juan to Los Angeles (SIG - LAX)
San Juan to Las Vegas (SIG - LAS)
San Juan to Houston (SIG - IAH)
San Juan to Newark (SIG - EWR)
San Juan to New York (SIG - JFK)
San Juan to Denver (SIG - DEN)
San Juan to Atlanta (SIG - ATL)
San Juan to San Francisco (SIG - SFO)
San Juan to Miami (SIG - MIA)
San Juan to Los Angeles (SIG - LAX)
San Juan to Las Vegas (SIG - LAS)
San Juan to Houston (SIG - IAH)
San Juan to Newark (SIG - EWR)
MDW to SIG Route Map
Chicago to San Juan Flights, Stats and Airplanes
Route information for flights from Midway Intl. to Fernando Luis Ribas Dominicci.
Origin:
Destination:
Distance:
2,054.38 miles
MDW - Midway Intl. Airlines
Browse the the most popular airlines servicing the Chicago (MDW) airport. Visit their flights pages to learn more about the most popular routes these carriers fly.
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