Cheap flights from Chicago to San Juan
The cheapest round trip from Chicago to San Juan that travelers found recently is $207 with a carry-on: a $207 fare on Southwest, which usually includes a carry-on. It leaves Wed, Jan 20 and comes back Mon, Jan 25.
Live prices for Wed, Jan 20 to Mon, Jan 25
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Wed, Jan 20 | Mon, Jan 25 | Southwest | MDW → SJU | 2 stops | $207 | Included | $207 | Live price |
| Sun, Jan 3 | Sat, Jan 9 | American Airlines | ORD → SJU | 1 stop | $409 | Included | $409 | Live price |
| Fri, Nov 20 | Mon, Nov 23 | Frontier | ORD → SJU | 1 stop | $338 | +$110 | $448 | Live price |
| Fri, Nov 6 | Mon, Nov 9 | Frontier | ORD → SJU | 1 stop | $346 | +$110 | $456 | Live price |
| Fri, Nov 27 | Mon, Nov 30 | Frontier | ORD → SJU | 1 stop | $381 | +$110 | $491 | Live price |
| Fri, Jan 15 | Mon, Jan 18 | Frontier | ORD → SJU | 1 stop | $444 | +$110 | $554 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| November 2026 | Fri, Nov 20 to Mon, Nov 23, 3 nights | $448 | Live price |
| January 2027 | Wed, Jan 20 to Mon, Jan 25, 5 nights | $207 | Live price |
Bag fees on this route
What the airlines flying Chicago to San Juan usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
| Southwest | Included | $35 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
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