Chicago to San Juan in October 2026
Round trips departing in October · Economy · Prices per person in USD
Prices updated
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when October fares drop below your price.October 2026 by departure day
Cheapest round trip leaving that day| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 1 | 2 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 $279 | 13 $236 | 14 | 15 $236 | 16 $228 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 $203 | 24 | 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
Empty days: no round trip found for that departure date yet. Green = cheapest third of the month.
Cheapest dates in October 2026
Round trip, per person-
Oct 23 – 26 3 nights · leave Fri$203Frontier Airlines 1 stop · 6h 18mBook
-
Oct 16 – 19 3 nights · leave Fri$228Frontier Airlines 1 stop · 5h 55mBook
-
Oct 13 – 22 9 nights · leave Tue$236Frontier Airlines 1 stop · 5h 59mBook
-
Oct 15 – 19 4 nights · leave Thu$236Frontier Airlines 1 stop · 5h 57mBook
-
Oct 12 – 22 10 nights · leave Mon$279American Airlines 1 stop · 5h 51mBook
Prices change often. The booking site shows the final price before you pay.
Cheapest by trip length
Good to know for October
October vs other months
Cheapest round trip per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $203 (cheapest month) |
| November 2026 | $226 |
| December 2026 | No fares found yet |
| January 2027 | $386 |
| February 2027 | No fares found yet |
| March 2027 | $428 |
| April 2027 | $329 |
| May 2027 | No fares found yet |
| June 2027 | $328 |
| July 2027 | $236 |
Chicago to San Juan in October: questions
What's the cheapest date to fly from Chicago to San Juan in October 2026?
Leaving Friday, October 23 and returning Monday, October 26 (3 nights) for $203 round trip on Frontier Airlines, the cheapest of the 5 date combinations we track that month.
How much is a round trip from Chicago to San Juan in October 2026?
From $203. Half of the 5 date combinations we track are under $236. Prices are per person in USD and change often.
Is October a cheap month to fly from Chicago to San Juan?
Yes. It's the cheapest of the 7 months ahead we have prices for.