Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.
Question : When traveling to Chicago from San Juan, how long will you be in the air?
Answer : When flying from SJU to MDW, it will take five hours and five minutes on average.
Question : Are you paying the cheapest or highest price for your ticket to Chicago?
Answer : Flight prices are fluctuating much more for this route than most routes from Puerto Rico, as they're ranging anywhere from $354 to $2,738. Prices tend to be lower the further out you book.
Question : What are the chances this flight will be delayed?
Answer : The San Juan to Chicago route has an 83% on-time rate, ranking in the 69th percentile worldwide in getting their passengers to their destinations on schedule. When there is a delay, it averages less than half an hour.
Question : For SJU to MDW, how many departure times are there on a given day?
Answer : Of course the day of the week matters, but on average, only one flight time exists when you fly from SJU to MDW. The average route departing Puerto Rico currently has six different flight times per day, so expect fewer choices than you're used to.
Question : Over the coming months, which airline is getting their passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Delta Air Lines is the leader in keeping prices down for their passengers over the next three months. Fares are being booked at just $354 and, when compared to the more expensive bookings of $2,738, it's quite a deal.
Question : How long does it take to get from SJU to MDW?
Answer : Southwest Airlines can get you there in five hours and five minutes. So, if you were to leave San Juan at 4:25 PM AST, you would arrive in Chicago at 7:30 PM CST (remember, there is a two-hour time change).
Question : When flying into Chicago, is Chicago Midway International Airport your cheapest option?
Answer : Chicago Midway International Airport is a great airport, but there is a cheaper option – O'Hare International Airport. It’s just 16 miles away and flights are being booked 35% cheaper over the coming two months.
Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Carolina to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.
Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with SJU to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Carolina for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.
All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.