Chicago to San Juan flights (ORD → SJU)
Looking for Chicago to San Juan flights? Cheapest round-trip I’ve found: US$208 on Frontier, 1 stop(s), departing 2026-10-16. That’s US$42 below the typical price for this route. Cheap flights from Chicago to San Juan change daily — I re-check this route three times a day.
Deal score: Exceptional — cheapest 10% we’ve seen — cheaper than 100% of prices I’ve seen on this route.
Best months to fly Chicago to San Juan
| Month | Cheapest seen |
|---|---|
| October | US$208 |
| December | US$217 |
| September | US$222 |
| August | US$228 |
| February | US$241 |
| November | US$252 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book Chicago to San Juan flights:
- Search Chicago to San Juan on Google Flights for the dates shown above (Oct 2026) — the fare I found is usually still available there.
- Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
- Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.
Fares change constantly. If the price has moved, check back — I re-check this route daily.
Other Chicago to … flights
- Chicago to Adelaide flights — US$1,321
- Chicago to Perth flights — US$1,226
- Chicago to Sydney flights — US$1,377
- Chicago to Chiang Mai flights — US$883
- Chicago to Lisbon flights — US$645
- Chicago to Brisbane flights — US$1,295
- Chicago to Sao Paulo flights — US$708
- Chicago to Warsaw flights — US$685
All flights to San Juan · All flights from Chicago
Prices last checked: 2026-09-25, 6:12:03 a.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.