About this route
Airlines serving both Chicago and San Juan include JetBlue, United Airlines, Condor and 3 more. We don't publish an award chart for this city pair yet, so use the search tool below to check live award pricing and availability across every program that flies it.
Airlines serving these airports
These carriers serve both ORD and SJU, non-stop or via a connecting hub.
JetBlue
B6
United Airlines
UA
Condor
DE
American Airlines
AA
Frontier Airlines
F9
Southwest Airlines
WN
When award seats open on this route
Booking tips
- Book 6-11 months in advance for the best premium cabin availability
- Compare programs before transferring — prices vary significantly between loyalty currencies
- Check our search tool for real-time Chicago to San Juan award availability
Keep planning this trip
Other award routes from Chicago
Frequently asked questions
Which loyalty programs can I use for ORD to SJU?
We don't publish an award chart for ORD–SJU yet, so search the route to see which programs price it and what they charge. Most major programs accept transfers from Amex, Chase and Capital One, so the currency you hold is rarely the constraint — availability is.
Ready to book Chicago to San Juan?
Search real-time award availability across every airline on this route.