- Fastest flight
- non-stop flights
- 46x / week
- Flight distance
- 3,318 km
- Time difference
- Airports in Chicago
- O'Hare International Airport, IL
- Midway International Airport, IL
- Rockford, IL
- Most popular airlines
- United Airlines
- American Airlines
- Spirit Airlines
- Southwest Airlines
- United Airlines
Flight schedule from Chicago (CHI) to San Juan (Puerto Rico) (SJU)
Select a travel date in the flight schedule for the route from Chicago (CHI) to San Juan (Puerto Rico) (SJU) and compare affordable flight deals.
offers
Active filtersnone
Matching outbound flightsCHI–SJU · 2 of 2
fromto
dep.arr.
durationstopovers
- September 20 – 26, 2026
- Sep 27 – Oct 3, 2026
- October 4 – 10, 2026
- ORDSJUnonstop
- ORDSJU1 stopover
Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)
Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.
American Airlines
29 %
Spirit Airlines
27 %
United Airlines
23 %
Important flight information
Frequently Asked Questions (FAQ)
How long is the flight from Chicago to San Juan (Puerto Rico)?
A nonstop flight from Chicago to San Juan (Puerto Rico) typically takes around 4 hours 40 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 11 hours 46 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
Are there nonstop flights from Chicago to San Juan (Puerto Rico)?
Yes, there are nonstop flights from Chicago to San Juan (Puerto Rico), averaging around 6 to 7 flights per day, operated by, among others, United Airlines, American Airlines and NK. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Which airlines fly from Chicago to San Juan (Puerto Rico)?
Direct flights from Chicago to San Juan (Puerto Rico) are operated by, among others, United Airlines, American Airlines and NK. Connecting flights with one stop are also available, for example with American Airlines (via Charlotte) and JetBlue Airways (via Fort Lauderdale). If travel time matters to you, a direct flight is usually the most convenient option. Connecting flights often give you more choice of departure times and airlines.
On which days are there nonstop flights from Chicago to San Juan (Puerto Rico)?
Nonstop flights from Chicago to San Juan (Puerto Rico) operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
How many flights are there per day from Chicago to San Juan (Puerto Rico)?
From Chicago to San Juan (Puerto Rico), there are on average around 6 to 7 flights per day. This usually means you have a good choice of departure times. If you are flexible, you can easily compare times, prices, and airlines.
How many flights per week are there from Chicago to San Juan (Puerto Rico)?
From Chicago to San Juan (Puerto Rico), there are around 46 to 47 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
When does the first flight from Chicago to San Juan (Puerto Rico) depart?
The earliest nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 7:40 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in San Juan (Puerto Rico).
When does the last flight from Chicago to San Juan (Puerto Rico) depart?
The last nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 10:40 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.