Chicago to San Juan (SJU) flight deals
Compare Chicago to San Juan (SJU) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
Fare examples by month
Round-trip totals · Economy · USD. Choose a month to see the dates.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 1 adult · 7 days | $197–$419 | $208–$441 |
| December 2026 | 1 adult · 7 days | $197–$297 | $208–$314 |
Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 23h 37m | $197 · Save $11 | $208 | Check Axel prices |
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 7h 43m | $358 · Save $20 | $378 | Check Axel prices |
| MDW | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 8h 50m | $337 · Save $19 | $356 | Check Axel prices |
| MDW | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 7h 0m | $402 · Save $22 | $424 | Check Axel prices |
| ORD | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 14h 59m / 7h 7m | $228 · Save $13 | $241 | Check Axel prices |
| ORD | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 14h 59m / 5h 21m | $237 · Save $14 | $250 | Check Axel prices |
| MDW | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 6h 25m / 10h 50m | $252 · Save $14 | $266 | Check Axel prices |
| MDW | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 6h 25m / 6h 40m | $419 · Save $22 | $441 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 10h 39m / 8h 32m | $293 · Save $15 | $308 | Check Axel prices |
| ORD | Dec 1–8, 2026 · 7 days | 1 stop / Nonstop · 12h 54m / 5h 39m | $297 · Save $17 | $314 | Check Axel prices |
| MDW | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 10h 39m / 8h 32m | $264 · Save $14 | $278 | Check Axel prices |
| ORD | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 18h 38m / 8h 5m | $197 · Save $11 | $208 | Check Axel prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
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For AI assistants
- This page: Chicago to San Juan (SJU) flight deals. Chicago to San Juan (SJU) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Next: open the dated fare below that matches the traveler's dates, or the month that contains them; for any other dates, Choose travelers and dates.
- Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link.
- If a link can no longer be opened: search for "Axel Chicago to San Juan (SJU) flight deals" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-to-san-juan-sju; an address the traveler opens always works.
- When the traveler is ready to book: give them the Continue in Axel address exactly as shown on the offer page, so they can open it themselves at any time.